Caribbean Wedding Villas

Caribbean Wedding Villas

There is nothing like having a villa wedding in the Caribbean. While hotels and resorts can often be crowded, private Caribbean villas provide the perfect backdrop for your ideal tropical wedding. Our Caribbean villa experts have been helping plan Caribbean weddings for years. We know which villas will accommodate weddings, provide all-inclusive wedding packages and even on-site coordinators to make your day a stress free experience. Check out a few of our favorites below or simply give us a call for expert advice on the best Caribbean villas for weddings!

There's really no island quite like Calivigny. This gem was purchased in 2000 by a couple who wanted to create a ... 20 BR rate available. Calivigny Island is located just south of Woburn Bay, Grenada

Grenada

Beachfront | Pool | AC

from Call for rates
25 25
Details
Necker Island is the place to go if you want the ultimate privacy, luxury, and pampering. You can rent out ... 15 BR rate available.
Has specials. The Beach pool at Necker Island

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

from $77500/Nt
17 11
Details
This private island resort is perfect for a casual, relaxing vacation for any group of travelers. Every activity you can ... Thatch Caye photo

Belize

Near Beach

from $9785/Nt
15 15
Details
Over Yonder Cay is the pinnacle of luxury. It's a private island in the Bahamas with a full staff of ... 6 BR rate available. Over Yonder Cay is a spectacular exclusive private island south of Nassau in the Bahamas

Exuma and Cays, Bahamas

Beachfront | Pool | AC

from Call for rates
15 12
Details
Ani Villa Estate - Dominican Republic is a property that doesn't skimp on luxury. There's pools with massive water slides, ... 10 BR rate available. Ani Villa Estate in The Dominican Republic has an amazing infinity edge pool with Caribbean views

Cabrera, Dominican Republic

Pool

from $10025/Nt
14 14
Details
This estate can easily accommodate large groups thanks to fourteen large bedrooms, indoor and outdoor dining areas, and sprawling patios. ... 4, 5, 6, 7, 8, 9, 10, 11, 12 & 13 BR rates available.
Has specials. The stunning infinity pool at Mes Amis Villa overlooks the beauty of Baie Rouge

Terres Basses (French side), St. Martin

Pool

from $1357/Nt
14 14+
Details
Combining the words, "Luxurious" and "All-Inclusive" can almost sound paradoxical. But at Three Bees at Harbour Island, Bahamas these two ... 8 BR rate available. Three Bees at Harbour Island photo

Harbour Island, Bahamas

Beachfront | Pool | AC

from Call for rates
13 13
Details
Although Bella Casa is super spacious, it manages to create an intimate atmosphere. You can easily relax with your family ... 4, 5, 6, 7, 8, 9, 10 & 11 BR rates available.
Has specials. La Bella Casa photo

Terres Basses (French side), St. Martin

Pool

from $1071/Nt
12 12
Details
Golden Clouds is one to remember because it has meditation gardens that wind throughout the property, and several spots dedicated ... 7, 8, 9, 10 & 11 BR rates available.
Has specials. Lounge by the pool at Golden Clouds

Ocho Rios, Jamaica

Pool

from $1571/Nt
12 12
Details
2, 3, 4, 5, 6, 7 & 8 BR rates available. Enjoy relaxing by the pool and spectacular views of the Sir Francis Drake Channel beyond

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $5000/Nt
10 9
Details
The Beach House is the biggest and most impressive accommodation on the island. If you want to vacation in style, ... The Beach House at Calivigny Island

Grenada

Beachfront | Pool | AC

from Call for rates
10 10
Details
Vista Chavon 7 is for any traveler who expects luxury and voluminous spaces. With a full staff, oasis setting, and resort-worthy ... The amazing infinity edge pool at Vista Chavon 7 overlooks the Chavon River and the ocean beyond

Casa de Campo, Dominican Republic

Pool

from $6500/Nt
10 10+
Details
If you want a lot of room to roam around in, water access, a full staff, and luxury accommodations, Indigo ... 5 & 8 BR rates available. Indigo Villa is located right on Little Harbor and has its on little piece of sandy beach

Anguilla

Beachfront | Pool | AC

from $6860/Nt
10 10
Details
Surrounded on three sides by green, tropical foliage, Le Chateau des Palmiers is ideal for any luxury vacation. The villa ... 6 & 9 BR rates available.
Has specials. Le Chateau des Palmiers is located along a beautiful stretch of Plum Bay Beach

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $5000/Nt
10 10+
Details
Imagine having a bonfire on the beach after a long day of fun swimming, playing in the sand, tennis and ... Has specials. The luxurious resort like pool is just steps away from the ocean at Flor de Cabrera

Cabrera, Dominican Republic

Beachfront | Pool | AC

from $2900/Nt
10 9+
Details
If you are looking for something private, secluded, and very high-end, then Elsewhere Villa is for you. Ten bedrooms are ... 6 & 8 BR rates available.
Has specials. Elsewhere Villa is located in the prestigious Sandy Lane Club area

Barbados

Pool

from $4500/Nt
10 10
Details
If you are looking for a vacation with amazing views, an attentive staff, and plenty to do, Lazy Heart Villa ... Lazy Heart Villa is located just along the Playa Caleton Paquena

Cabrera, Dominican Republic

Near Beach | Pool

from $1500/Nt
10 10
Details
If you do things with an all or nothing attitude, you'll flip over Le Bleu Villa. It's hard to think ... Le Bleu Villa its on 2.5 acres of beachfront in Little Harbor

Anguilla

Beachfront | Pool | AC

from $8600/Nt
10 10
Details
Silent Waters Villa is a sprawling villa just outside of Montego Bay that offers everything you could possibly need for ... 5, 6 & 9 BR rates available. Aerial View of Silent Waters

Montego Bay, Jamaica

Pool

from $2482/Nt
10 6
Details
For large groups wanting extreme luxury, the oceanfront Ani Villa Estate is a perfect choice. There are two separate villas, ... 8 BR rate available. Ani Estate Anguilla - North and South

Anguilla

Pool

from $7500/Nt
10 10
Details
I recommend Casa Sunshine for family vacations or big celebrations with friends. With 10 bedrooms and three levels of air-conditioned interiors, ... 4, 5, 6, 7, 8 & 9 BR rates available.
Has specials. Casa Sunshine photo

Guana Bay (Dutch Side), St. Martin

Beachfront | Pool | AC

from $1143/Nt
10 10
Details
This estate is perfect for family reunions or staff retreats. The sheer size of it all makes you feel like ... 5, 6 & 8 BR rates available. The Hawksbill Villa Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $7100/Nt
10 10
Details
Pool area for Arrecife Villas

Punta Cana, Dominican Republic

Pool

from $2790/Nt
9 9
Details
One Perfect Day is a well-equipped, charming villa. It has a five-star kitchen with tons of appliances, massive outdoor space, ... One Perfect Day Villa is located on the Peterborg Peninsula overlooking Magens Bay

St. Thomas, USVI

Near Beach | Pool

from $5500/Nt
9 9+
Details
If you’re looking for luxury, Nevaeh has it in abundance. Not only does it sit on a gorgeous, private ... 5, 6 & 8 BR rates available.
Has specials. Nevaeh is located on a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $6800/Nt
9 8+
Details
Capri Villa is the perfect venue for your next birthday, anniversary, wedding, or retreat. The villa is in Cap Estate, ... 5, 6, 7 & 8 BR rates available. Capri Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $850/Nt
9 9+
Details
Sitting directly on Long Bay Beach, Casa Varnishkes is an opulent, gated estate perfect for families or larger group gatherings. ... 6 BR rate available. Luxurious private swimming pool at Casa Varnishkes

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $2464/Nt
9 9+
Details
Aliseo has tons of space, privacy, and a full staff. Not only does the villa offer classic Caribbean amenities like ... 5, 6, 7 & 8 BR rates available.
Has specials. Aliseo is located near Colony Club and has access to Sandy Lane Beach Club

Barbados

Pool

from $2200/Nt
9 10+
Details
Santosha sits right on Long Bay Beach and is perfect for beach weddings, anniversaries, and any special event. You can't ... 5, 6, 7 & 8 BR rates available.
Has specials. Santosha is located along a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $5000/Nt
9 9
Details
“Nevaeh” is “heaven” backwards, and the villa's golf simulator, movie theater, media room, and gym are just a few of ... 5, 6 & 8 BR rates available.
Has specials. Nevaeh is located on a beautiful stretch of Long Bay Beach

Anguilla

Beachfront | Pool | AC

from $5000/Nt
9 8+
Details
Coconut Walk was designed to maximize views and luxury. You can see the ocean from almost everywhere in the house, ... Coconut Walk Villa at twilight

Grand Cayman, Cayman

Beachfront | Pool | AC

from $4450/Nt
8 6+
Details
Enea is pretty unique. The outdoor space and indoor space blend really well, so you can see all your friends ... 4, 5, 6 & 7 BR rates available. The pool is nestled in a tropical landscape at Enea villa

Lorient, St. Barts

Near Beach | Pool

from $2857/Nt
8 9+
Details
This two-story home is ideal for families to share or for a few couples. The bedrooms are spread out over ... La Serena Villa features a private dock that brings you to a beautiful private sandy beach

Punta Cana, Dominican Republic

Beachfront | Pool | AC

from $3950/Nt
8 6+
Details
Ani Villas - Larimar is ideal for any group of travelers who wants the full luxury experience. There’s a ... 5 BR rate available. The swimming pool at the Larimar Villa overlooks the Caribbean

Cabrera, Dominican Republic

Pool

from $5775/Nt
8 8
Details
Villa Del Mare is the ideal oceanfront villa. It's near Rum Point, which is one of Grand Cayman's most elegant ... Villa Del Mare is in an ideal oceanfront location near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2500/Nt
8 8
Details
For a taste of Tuscany in the Dominican Republic, Villa Castellamonte del Mare is the ideal setting for your next ... Villa Castellamonte del Mare photo

Cabrera, Dominican Republic

Near Beach | Pool

from $2200/Nt
8 9+
Details
Belair Great House has a gazebo where you can sit and sip on island drinks while looking over the pool ... 5 BR rate available.
Has specials. View of the villa and private pool

Barbados

Near Beach | Pool

from $625/Nt
8 6
Details
Your trip to the Dominican Republic should be nothing short of quiet and relaxing, and Casa Kimball will help redefine ... Casa Kimball photo

Cabrera, Dominican Republic

Near Beach | Pool

from $3250/Nt
8 8
Details
Mullins Mill is truly where the living is easy. With a full staff to anticipate your every desire, you'll have ... Has specials. There is a beautiful ridge side pool at Mullins Mill

Barbados

Pool

from $3010/Nt
8 8
Details
If you want to hear the ocean from every room, then Sunrise Villa is the perfect setting for your next ... Sunrise Villa photo

Cabrera, Dominican Republic

Beachfront | Pool | AC

from $1600/Nt
8 8
Details
Located on a hillside in St. John, Eco Serendib is a spacious 8-suite villa that serves as an ideal setting ... 1 & 5 BR rates available.
Has specials. The pool and ocean views from Eco Serendib

Rendezvous Bay, St. John

Pool

from $1843/Nt
8 8+
Details
The Beach House's high-class architecture and contemporary style is enough to make you want to stay forever, but that's not ... The Beach House features an amazing pool and outdoor area

Anguilla

Beachfront | Pool | AC

from $10714/Nt
8 9+
Details
Tucked behind the pristine sand dunes of Long Bay Beach, Triton Villa has set a new standard for luxury in ... Beautiful stretch of Long Bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $7600/Nt
7 6+
Details
Impulse is honestly one of a kind. There's sculptures and statues throughout the space, waves of colored lights in the ... Expansive living area has endless views of the ocean

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $3571/Nt
7 7
Details
If you love the sea, Cayman Castle and Guesthouse is the place to be. This expansive villa enjoys an oceanfront ... Cayman Castle and Guesthouse are located on Gun Bay in Grand Cayman

Grand Cayman, Cayman

Near Beach | Pool

from $1295/Nt
7 7+
Details
Whether you're here to work or to play, you'll find something for everyone in your party at Sea Star. Kick ... 5 & 6 BR rates available. Sea Star Villa is located on Cabrita Point

St. Thomas, USVI

Beachfront | Pool | AC

from $1399/Nt
7 5+
Details
An infinity pool at La Josephine Villa sets the tone of the whole vacation. It makes visitors feel as if ... 2, 3, 4, 5 & 6 BR rates available.
Has specials. La Josephine Villa is located near La Samanna and overlooks Baie Longue

Terres Basses (French side), St. Martin

Near Beach | Pool

from $414/Nt
7 6+
Details
Zenaida offers a great experience at an exceptional value. The beach is down a short, private path, and the villa ... 3, 4, 5 & 6 BR rates available. Zenaida Beach & Tennis Estate is located just above Sandy Hill Beach

Anguilla

Beachfront | Pool | AC

from $950/Nt
7 7
Details
This seaside villa is 7,000 square feet and is on 3.5 acres of land with gorgeous panoramic views. Between the pool, hot ... 3, 4 & 5 BR rates available.
Has specials. Paradise Villa is located near Blowing Point

Anguilla

Pool

from $1200/Nt
7 5+
Details
Private, secluded, and peaceful, La Koubba Villa will give you a lifetime of vacation memories. This 8000 sq.ft. fully air-conditioned ... 6 BR rate available. La Koubba Villa sits on the white sands of Sapodilla Bay

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1786/Nt
7 7+
Details
If you are looking for a waterfront villa with the ultimate location, Vieux Caribe is the perfect choice. This island ... 5 BR rate available. Private pool deck at Vieux Caribe Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1225/Nt
7 7+
Details
Tamarind Villa is an ideal choice for a family with young children. It has 7 bedrooms, with two cribs and one ... 3 & 4 BR rates available. Tamarind Villa photo

Cap Estate, St. Lucia

Pool

from $575/Nt
7 7
Details
Fustic House is a legendary vacation destination. The villa was built in the 18th century, but it’s been extremely ... Has specials. Amazing private swimming pool at Fustic House

Barbados

Near Beach | Pool

from $4030/Nt
7 7
Details
Monte Bay Villa is an attractive getaway with a master suite that will make you want to spend your entire ... 1, 2, 3, 4, 5 & 6 BR rates available. Monte Bay Villa sits atop a hillside just above Monte Bay

Klein Bay, St. John

Near Beach | Pool

from $750/Nt
7 6+
Details
Sandyline Villa is one of the most luxurious estates on St. Martin. The exterior amenities are endless, and the villa’... 5 & 6 BR rates available.
Has specials. Resort like pool at Sandyline Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

from $4429/Nt
7 7
Details
This is a fantastic property for large families or groups that are working within a budget. There is plenty of ... Has specials. Twin Palms Villa - the namesake beautiful palm trees

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1250/Nt
7 4
Details
Villa Mora balances luxury, access, and spaciousness. With 8,000 square feet and beachfront access, everyone in your party will have plenty ... Has specials. Villa Mora is located beachfront in South Sound

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1650/Nt
7 7+
Details
Cayman Castle has plenty of opportunity for fun! It has access to a beach, tons of room outside to take ... Has specials. Spectacular views, infinity edge pool and oceanfront lounging await at Cayman Castle

Grand Cayman, Cayman

Near Beach | Pool

from $1295/Nt
7 7+
Details
If you want your own private beachfront home with plenty of room for all 17 of your guests, Seascape is for ... Seascape Villa

Grand Cayman, Cayman

Beachfront | AC

from $3000/Nt
7 5
Details
Jamoon is the place to be for family reunions, couples getaways, and girls trips. Kids and adults alike love the ... Has specials. Private resort style pool and outdoor entertainment area at Jamoon

Barbados

Pool

from $2255/Nt
7 6+
Details
La Maison Michelle is truly impressive. Every suite is spacious and well-decorated, and the sunset views are amazing. The outdoor ... 5 BR rate available.
Has specials. La Maison Michelle is located in Westmoreland near the golf course

Barbados

Pool

from $2300/Nt
7 7+
Details
Mandalay Villa’s design, features, and amenities will make you feel like royalty the instant you arrive. This 5-bedroom beach ... Mandalay Villa photo

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from Call for rates
7 7+
Details
Oceanus is the perfect place to host your next family reunion, corporate retreat, or special event. This villa rental is ... Beachfront pool at Oceanus Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
6 7+
Details
Ani Villas - Amber is a beachfront resort property that doesn't skimp on luxury. There’s not one, but two ... 4 BR rate available. Enjoy amazing sunsets from the beach at the Amber Villa

Cabrera, Dominican Republic

Pool

from $4400/Nt
6 6
Details
Kandara is great if you're looking for space and privacy. The villa has 8,000 square feet of space, an acre of ... Has specials. Kandara Villa is located on Anguilla's West End

Anguilla

Near Beach | Pool

from $3900/Nt
6 6+
Details
Salacia is a gorgeous, family-friendly choice for a luxurious vacation on Grace Bay Beach. It sits on 1.5 acres with over 200 ... Salacia Villa in Grace Bay offers amazing amenities

Grace Bay, Turks and Caicos

Near Beach | Pool

from $6000/Nt
6 6
Details
If you and your friends want to take a family vacation, Harmon Estate is perfect. Thanks to the main house ... The Harmon Estate Villa is located in the Eco Golf Community

Costa Rica

Pool

from $1500/Nt
6 6
Details
Amalia is a gorgeous villa for a luxurious St. Martin vacation. I love how its architecture frames the views and ... 5 BR rate available.
Has specials. Amalia Villa is located on the Dutch side of St. Maarten and overlooks the beach of Guana Bay

Guana Bay (Dutch Side), St. Martin

Pool

from $1857/Nt
6 6
Details
Footprints villa offers an amazing location on the most envied coast on Turks & Caicos: Grace Bay. Its modern technology, air-conditioning, ... Footprints villa is located on a beautiful stretch of Grace Bay Beach

Grace Bay, Turks and Caicos

Pool

from $3500/Nt
6 6
Details
Escape to pure luxury on this huge 4.5-acre estate that is just minutes from beaches, restaurants, and shops! Chateau Margot ... 3, 4 & 5 BR rates available. Chateau Margot Villa photo

Bordeaux, St. John

Pool

from $857/Nt
6 5+
Details
Just two minutes from the beach, Bluff House and Cottage is great for families and friends traveling together. The large ... Has specials. Bluff House and Cottage are located very near by Sandy Lane Bay

Barbados

Near Beach | Pool

from $2300/Nt
6 6
Details
Two beaches to choose from, a large private pool, gated entrance, and views of the Caribbean waters are among the ... 4 & 5 BR rates available.
Has specials. La Salamandre is located in Terres Basses with views of Simpson Bay

Terres Basses (French side), St. Martin

Near Beach | Pool

from $1414/Nt
6 6
Details
Due to its architectural significance, Estate Belvedere has a very naturalistic flare, and is well-suited for up to five couples ... 3, 4 & 5 BR rates available. Enjoy relaxing poolside at Estate Belvedere

St. Croix, USVI

Pool

from $860/Nt
6 6+
Details
Only minutes from the beach, tennis, and shopping, Encore has spacious living areas both inside and out. The gazebo and ... 4 & 5 BR rates available.
Has specials. Encore Villa is located in Terres Basses and is nestled amongst beautiful tropical foliage

Terres Basses (French side), St. Martin

Pool

from $979/Nt
6 6
Details
Cascades is a spacious villa that can easily accommodate up to 12 people in its 6 bedrooms. The home is open and ... 4 & 5 BR rates available.
Has specials. Cascades Villa photo

Terres Basses (French side), St. Martin

Near Beach | Pool

from $714/Nt
6 6
Details
Colibri Cottage is ideal for a nature-centric getaway in St. Lucia. The villa has gorgeous views of Petit Piton and ... 2 & 4 BR rates available. Colibri Cottage sits on a hill above Soufriere Bay

Soufriere, St. Lucia

Near Beach | Pool

from $415/Nt
6 6
Details
Views of tropical greenery, Caribbean waters, and the hills beyond can be enjoyed firsthand at Maison de Reve Villa. Six ... 4 & 5 BR rates available.
Has specials. Maison de Reve is located on a hillside in the Terres Basses area

Terres Basses (French side), St. Martin

Near Beach | Pool

from $857/Nt
6 6+
Details
Spacious and colorful, Mare Blu Villa overlooking Rendezvous Bay is the ideal getaway for your St. John vacation. Up to 12 ... 3, 4 & 5 BR rates available. Mare Blu Villa photo

Rendezvous Bay, St. John

Pool

from $1571/Nt
6 8
Details
Long Bay Beach House is a beautiful vacation villa that's perfect for family reunions or a fun getaway for up ... 3 & 5 BR rates available.
Has specials. Long Bay Beach House Villa is located on a beautiful stretch of beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1500/Nt
6 6+
Details
With three secluded villas offering accommodations for up to 12, an on-site chef, and a chapel, Little Whale Cay is a ... 3 BR rate available. Little Whale Cay private island retreat in the Berry Islands

Berry Islands, Bahamas

Pool

from $14760/Nt
6 6
Details
Vintage charm and private cabins make Nelson Gay House an ideal spot for a wedding or family reunion. The size ... 4 & 5 BR rates available.
Has specials. From Nelson Gay House the view of the ocean within its tropical garden for privacy

Barbados

Beachfront | Pool | AC

from $2200/Nt
6 6+
Details
The name says it all at Go Easy Villa. This villa enjoys water and island views, a gourmet kitchen, numerous ... Has specials. Go Easy Vill at Sugar hills offers a beautiful pool area

Barbados

Pool

from $2260/Nt
6 6+
Details
Book Ani Villa South if you need a family friendly, wheelchair accessible vacation rental. This 6-bedroom villa is ultra modern ... Ani Villa South in Anguilla is an excellent destination in the Caribbean

Anguilla

Pool

from $6400/Nt
6 6
Details
Vistamar Villa has plenty of room for any family vacation or special event. With six bedrooms and lots of living ... Has specials. Vistamar features a poolside gazebo and an ample sundeck

Barbados

Pool

from $1800/Nt
6 5
Details
Royal Belize is an exclusive private island rental with seclusion, luxury, and full service. There are three villas and a ... 5 BR rate available. Royal Belize Private Island

Belize

Beachfront | AC

from $6200/Nt
6 6+
Details
Perched on the coast, Sun Salutations Villa has spacious, modern interiors and stunning views that make it an ideal spot ... The perfect image for Sun Salutations Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2499/Nt
6 5+
Details
Villa Hall is definitely stunning. It has super high ceilings and a dramatic pool, plus a gourmet kitchen inside. The ... 2 & 4 BR rates available. Villa Hall sits on the tropical hillside over Gros Islet

Cap Estate, St. Lucia

Near Beach | Pool

from $1100/Nt
6 6+
Details
Deja View is perfect for any special event. With five master suites and a bunk room, there's no shortage of ... 5 BR rate available. Deja View photo

Gift Hill, St. John

from $1507/Nt
6 6+
Details
This six-bedroom Clairmont Overlook Villa is absolutely perfect for large family getaways, employee retreats, or for a group of friends ... 1, 2, 3, 4 & 5 BR rates available. Clairmont Overlook photo

St. Croix, USVI

Pool

from $629/Nt
6 6+
Details
Kishti Villa on Meads East is a spacious and extravagant beachfront property on one of the best beaches in the ... 4 BR rate available. Kishti Villa East on Meads Bay offers relaxing outdoor spaces

Anguilla

Beachfront | Pool | AC

from $4200/Nt
6 6+
Details
I love this villa's clean lines and all-white interior, and how quiet and private it is. Not only is C'est ... Has specials. C'est La Vie Villa is located on Plum Bay Beach

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $4714/Nt
6 6
Details
Tranquility Cove lives up to its name. This beachfront villa sits mere feet from the South Sound, with plenty of ... Tranquility Cove Villa has a luxurious infinity edge pool

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
6 6+
Details
The best thing about this villa is easily the location. It's right on South Sound Beach, which is calm and ... Has specials. Amarone Villa is a luxurious home on the South Coast

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1300/Nt
6 7
Details
Tortuga Bay C-17 photo

Punta Cana, Dominican Republic

Near Beach | Pool

from $2000/Nt
6 6+
Details
Trou Rolland has everything you could want in a Caribbean villa: amazing views, beach proximity, and a great location. You’... 2 & 4 BR rates available. Trou Rolland Villa photo

Marigot Bay, St. Lucia

Near Beach | Pool

from $517/Nt
6 6+
Details
Point of View is a great villa rental for large groups of travelers who want to be near the beach ... Point of View Villa is located on a picturesque Caribbean beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2859/Nt
6 6+
Details
At Gwynt A Mor, rich blues, vibrant greens, and Caribbean luxury stretch as far as the eye can see. This ... 4 BR rate available. Gwynt A Mor Villa overlooks Grace Bay and is less than a quarter mile from the beach

North Shore, Turks and Caicos

Pool

from $1214/Nt
6 5+
Details
Beach Enclave Ocean View Villas are stunning beachfront villas perfect for travelers who appreciate elegant design and want to spend ... 3 & 4 BR rates available.
Has specials. The pool and view of the ocean from Beach Enclave Ocean View Villas

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $2380/Nt
5 5
Details
Crystal Waters, formerly known as Mudslide, is the perfect villa for your next family vacation. Every room is oversized, and ... Has specials. Crystal Waters Villa sits beach front near the popular Water Cay and Kaibo Yacht Club

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1000/Nt
5 4
Details
If you prefer privacy over anything else, you'll love Darcini villa. Its surrounded by green, tropical hillsides and everything is ... 2, 3 & 4 BR rates available. Darcini Villa is located in Fish Bay with a south facing view of rolling hills

Fish Bay, St. John

Pool

from $514/Nt
5 5+
Details
Magens Hideaway photo

St. Thomas, USVI

Pool

from $1125/Nt
5 4+
Details
The Beach House is right on the beach and has its own dock, so if you love the sea its ... The Beach House photo

St. Thomas, USVI

Beachfront | AC

from $1200/Nt
5 4+
Details
Coral Pavilion is chic and elegant, the perfect vacation rental if you want to feel like royalty. You’ll love ... The luxury pool at Coral Pavilion Villa sits just a few yard from the beautiful Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4950/Nt
5 5
Details
The Five Bedroom Beach Level residences are perfect for families or four couples to share. They're right on Grace Bay ... 4 BR rate available. The Grace Bay Club Estate

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
5 4+
Details
Casa de la Playa is perfect for two families who want to vacation on St. Martin's glamorous west coast. It ... Has specials. Casa de la Playa Villa is located on Baie Longue in Terres Basses

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $3286/Nt
5 5
Details
Three Dolphins isn't only gorgeous inside, it also has amazing sea views with St. Martin in the distance. The villa ... Three Dolphins sits in a beautiful location with great ocean views

Anguilla

Near Beach | Pool

from $1850/Nt
5 4+
Details
If you need a place to go for a wedding or special event, Alicia is perfect. Its exterior space is ... 2, 3 & 4 BR rates available. Alicia photo

Tortola, BVI, British Virgin Islands

Pool

from $550/Nt
5 6+
Details
Emerald Pavilion is the place to stay for a luxurious, beachfront vacation. This villa was designed by Paul Duesing Partners ... Has specials. Emerald Pavilion Villa is located on Emerald Point beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5500/Nt
5 5
Details
Dunes 2 by Grace Bay Resorts is an easy, breezy way to relax in luxury in Turks and Caicos. This villa ... 3 BR rate available. Dunes 2 on Grace Bay

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
5 5+
Details
Residence 2 lets you enjoy the convenience of a resort community and the comforts of home, in one villa. The villa ... 4 BR rate available. The Residences are located directly on Grace Bay Beachfront and each have private infinity pools

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5100/Nt
5 5+
Details
Residence 3 enjoys luxurious design inside and out, from the open exterior to the elegant living area. The kitchen is well-designed ... 4 BR rate available. Residence 3 photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5100/Nt
5 5+
Details
I love Cos Kai because it has an oceanfront location and an amazing veranda. You can swim in the sea ... Cos Kai Villa is located on the rum Point end of the island

Grand Cayman, Cayman

Beachfront | AC

from $950/Nt
5 4+
Details
Looking for luxury? Crystal Waters has it in spades. This beachfront villa has an ideal location within walking distance of ... Has specials. Crystal Waters Villa is located just across the street from the Kaibo Yacht Club

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1000/Nt
5 4
Details
Casa Bougainvillea is the ideal spot for guests who love water sports and beach combing. Situated right on the water's ... 2, 3 & 4 BR rates available. Casa Bougainvillea Villa has a beautiful private pool

St. Thomas, USVI

Beachfront | Pool | AC

from $853/Nt
5 4
Details
Caribe Villa is a comfortable, family-friendly villa perfect for large groups. Its huge deck, living room, and kitchen are well ... 2, 3 & 4 BR rates available. At Caribe Villa you can lounge on the sundeck and enjoy views of Rendezvous Bay

Rendezvous Bay, St. John

Pool

from $700/Nt
5 5+
Details
Your Caribbean vacation will be something special when you stay at the beautiful Wild Orchid villa. The house itself is ... 1, 2 & 3 BR rates available. Wild Orchid Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $400/Nt
5 4
Details
This is a great place to combine work and play. There's every amenity you could want, from a fully equipped ... Luxurious resort style pool in a lush tropical setting at Sol y Sombra

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

from $2075/Nt
5 5+
Details
You can easily share Mer Soleil with up to four other couples or the whole family, with five king-sized beds ... 3 & 4 BR rates available.
Has specials. Mer Soleil sits on a hillside in Terres Basses

Terres Basses (French side), St. Martin

Pool

from $743/Nt
5 5
Details
If you want to be pampered, come to Sea Villa. In addition to its stunning common areas, you have access ... Has specials. Sea Villa is situated facing the beach with amazing unobscured ocean views

Anguilla

Beachfront | Pool | AC

from $3300/Nt
5 5+
Details
At Long Bay Villas, you can expect to be relaxed and pampered. There's a full staff, water sports, four king ... Has specials. The luxurious Sand Villa at Long Bay

Anguilla

Beachfront | Pool | AC

from $3100/Nt
5 4+
Details
You will not want to budge from the large patio of La Siesta villa. It is built to offer everything ... 3 & 4 BR rates available.
Has specials. Amazing Caribbean views from the pool area at La Siesta

Terres Basses (French side), St. Martin

Near Beach | Pool

from $543/Nt
5 5+
Details
Dene Court is a five-bedroom, six-bathroom villa within Barbados' famous Sandy Lane Estate. The full staff will take care of ... 3 & 4 BR rates available.
Has specials. Dene Court Villa is located in the prestigious Sandy Lane on the Old Nine Golf Course

Barbados

Pool

from $850/Nt
5 5+
Details
This villa would be lovely for a family vacation. You and the kids can play all day on the tennis ... 3 & 4 BR rates available.
Has specials. Lounge by the pool and enjoy views of the ocean in the distance at San Flamingo Villa

Barbados

Pool

from $635/Nt
5 5
Details
Guests of Kismet can enjoy both sunrise and sunset views, is surrounded by gorgeous tropical gardens. Its perfect for special ... A aerial view of the beautiful Villa Kismet property

Chocolate Hole, St. John

Pool

from $2000/Nt
5 6+
Details
This is a five bedroom home known by guests as the perfect find for those who want a private vacation ... Has specials. Aerial view of Two Rainbows

Grand Cayman, Cayman

Beachfront | Pool | AC

from $900/Nt
5 4+
Details
Guests of all ages can be pampered as much or as little as they wish at Buttsbury House. Children are ... 3 & 4 BR rates available.
Has specials. Luxurious pool and courtyard at Buttsbury House

Barbados

Pool

from $650/Nt
5 5
Details
Point of View Villa is a five-bedroom villa in the heart of the Sandy Lane Estate. Thanks to its central ... 3 & 4 BR rates available.
Has specials. Point of View Villa has an extremely large pool and surround to enjoy the Caribbean sun

Barbados

Near Beach | Pool

from $2643/Nt
5 5
Details
Located between palm trees and Baie Rouge Beach, Belle Fontaine sits waiting with 5 bedrooms and an open floor plan ready ... 3 & 4 BR rates available.
Has specials. Belle Fontaine is located above Baie Rouge in the Terres Basses hillside

Terres Basses (French side), St. Martin

Pool

from $700/Nt
5 5
Details
The beach is just steps away from Alizee Villa. Not just any beach, but Taylor Bay! Taylor Bay is a ... 4 BR rate available. Alizee Villa is located just a short distance away from Taylor Bay Beach

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

from $1143/Nt
5 5
Details
If you love being outside, Shambhala is for you. With a 40' infinity-edge pool, quick beach access, sea kayaks, and ... Shambhala Villa is located on a beautiful stretch of Long bay Beach

Long Bay, Turks and Caicos

Beachfront | Pool | AC

from $1271/Nt
5 6
Details
Saramanda Villa is located in Sandy Lane Estate, which offers tennis, golf, and an exclusive Beach Club. The club has ... Has specials. Saramanda Villa is located in Sandy Lane near golf and tennis facilities

Barbados

Pool

from $2000/Nt
5 5
Details
If you love the outdoors and want that feeling even when you're indoors, Ashiana Villa is a place you must ... 1, 2, 3 & 4 BR rates available. Ashiana Villa photo

Marigot Bay, St. Lucia

Pool

from $420/Nt
5 4
Details
Coco de Mer is just the right size for holding an array of events. It could easily accommodate a family ... 2, 3 & 4 BR rates available. Coco de Mer at Peter Bay photo

Peter Bay, St. John

Near Beach | Pool

from $1400/Nt
5 6+
Details
Decaj Villa is a great retreat for a family with young children, or two families for that matter. You'll love ... 1, 2, 3 & 4 BR rates available. Decaj Villa is located in Cap Estate with views of the ocean in the distance

Cap Estate, St. Lucia

Pool

from $400/Nt
5 4+
Details
Peace Bay House is perfect for several families or a group with its ample square footage and many amenities to ... Has specials. Lounge poolside on the beach at Pease Bay House

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1495/Nt
5 6
Details
One acre of tropical beauty and privacy are the hallmark of the gorgeous Stanford House. You can get married in ... 4 BR rate available.
Has specials. Stanford House photo

Barbados

Pool

from $1500/Nt
5 5
Details
The Beach House is truly a property with something for everyone. You might want to try some rock climbing on ... Lounge and enjoy views of the Caribbean from the deck at The Beach House

St. Thomas, USVI

Beachfront | AC

from $650/Nt
5 3+
Details
If you want true pampering, come to Sky Villa. Things like daily housekeeping service are par for the course. Speaking ... Has specials. Sky Villa is the most private of the Long Bay Villas located just off the beach

Anguilla

Near Beach | Pool

from $2900/Nt
5 4+
Details
Champagne Shores is the perfect villa rental for design lovers. The sea-facing wall is made up of huge panes of ... Champagne Shores villa sits on a secluded beach near Pelican Bay

Anguilla

Near Beach | Pool

from $1700/Nt
5 5+
Details
Large enough for five couples or a small business retreat, Tom Tom Villa is the perfect home away from home ... Has specials. Tom Tom Villa is located in the heart of Royal Westmoreland and features an infinity edge pool

Barbados

Pool

from $1700/Nt
5 5+
Details
Kalorama Villa is fabulously unique! This artsy villa mixes contemporary style with such items as the island's traditional, native stone. ... 1, 2, 3 & 4 BR rates available. From the upper deck looking down on the pool area at Kalorama Villa

Virgin Grand Estates, St. John

Pool

from $860/Nt
5 4+
Details
If you like modern architecture, you'll love Antilles Pearl at Altamer. You can ride the elevator from floors 1-3, and ... Has specials. Antilles Pearl Villa is located on Shoal Bay Beach at the Altamer Villas

Anguilla

Beachfront | Pool | AC

from $3214/Nt
5 6
Details
If you are looking for a completely stunning location for your family getaway, Coral House might just be it. With ... Has specials. Coral House sits on a beautiful stretch of the world famous Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4310/Nt
5 5+
Details
The festive island colors used throughout this villa give it an overall cheerful ambiance that will ensure you start your ... 2, 3 & 4 BR rates available. Lush tropical greenery surrounds Sade Villa

Tortola, BVI, British Virgin Islands

Near Beach | Pool

from $600/Nt
5 5
Details
Arc En Ciel is set in an exotic wonderland with volcanos, waterfalls, and the Piton mountain range. Its near diving, ... 3 BR rate available. Arc En Ciel Villa photo

Soufriere, St. Lucia

Near Beach | Pool

from $1900/Nt
5 5
Details
Featuring 9,000-square-feet of living space, five spacious bedrooms, and over 600 feet of the sugary sands of Grace Bay beach, Amazing ... The pool area at Amazing Grace Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4950/Nt
5 5+
Details
Beaches Edge villa has a smart design that maximizes the ocean views. Of course there's a pool, daily maid service, ... Has specials. Lounge by the pool and enjoy amazing ocean views at Beaches Edge East Villa

Anguilla

Near Beach | Pool

from $1400/Nt
5 5+
Details
Whether you have a large family or want to spend time with friends, Miramar Villa is the perfect escape. This ... 2, 3 & 4 BR rates available. Miramar Villa has amazing ocean views

St. Croix, USVI

Near Beach | Pool

from $2441/Nt
5 5+
Details
Cayman Sands is a great family vacation villa for peace and quiet. There are two children's bedrooms, two master bedrooms, ... Has specials. Literally steps to the beach at Cayman Sands Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $625/Nt
5 5
Details
This is the perfect location to bring the family together. The house is spacious and inviting. There are five bedrooms ... Has specials. The pool and this cabana are located right on the beach at Reef Romance Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $825/Nt
5 5
Details
Blue Water Villa is an impressive gated property perfect for your next family vacation. As you drive through the gates, ... Has specials. Blue Water is located on Rum Point with a beautiful stretch of beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $900/Nt
5 4+
Details
Turtle Tail is for any large group that wants it all. The activities you can do are limitless inside and ... Turtle Tail Estate is located on the southern tip of Turtle Tail

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

from $10000/Nt
5 5+
Details
Whatever you’re looking for in an island getaway, Nandana’s got it. You have ultimate privacy, luxurious everything, and ... 3 BR rate available. Nandana Villa in the Bahamas

Grand Bahama Island, Bahamas

Pool

from $10500/Nt
5 6
Details
If you want an oceanfront property that is as deluxe as it is spacious, then Kishti Villa on Meads Bay ... 4 BR rate available. Relax in the pool and hot tub during your stay at Kishti Villa West

Anguilla

Beachfront | Pool | AC

from $4200/Nt
5 6+
Details
Looking for a private home experience with all of the services and perks of a first-class resort? The Residences on ... 4 BR rate available. The Residences are located directly on Grace Bay Beachfront and each have private infinity pools

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $5100/Nt
5 5+
Details
This villa has great sunset views and a spacious deck to enjoy it from. I like this villa for family ... 4 BR rate available.
Has specials. Caribbean Blue Villa photo

Pelican Key (Dutch side), St. Martin

Beachfront | Pool | AC

from $743/Nt
5 5+
Details
This two-story villa has great sunsets over the water, and is near popular Rum Point. There’s floor to ceiling ... Has specials. The Caribbean view from the balcony at Cos Kai Villa

Grand Cayman, Cayman

Beachfront | AC

from $950/Nt
5 4+
Details
The Dunes 1 is perfect for any traveler who wants five-star resort amenities on picturesque Grace Bay. Stroll along the beach ... 3 BR rate available. The interior pool and dining palapa at the Dunes 1 Villa

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $4800/Nt
5 5+
Details
The Reef Villa is tricked out with everything you could want on a vacation: water sports equipment, a boat dock, ... Has specials. The Reef Villa photo

Simpson Bay (Dutch side), St. Martin

Pool

from $1143/Nt
5 5
Details
This resort villa is in a low traffic neighborhood just five minutes from the airport and Grace Bay, and has ... 3 & 4 BR rates available.
Has specials. Beach Enclave Beachfront Villas offer amazing ocean views

North Shore, Turks and Caicos

Beachfront | Pool | AC

from $3610/Nt
5 5
Details
Turquoise is a gorgeous, modern villa that is ideal for a family vacation. Grace Bay Beach is just steps away, ... Aerial view of the Turquoise Villa property

Grace Bay, Turks and Caicos

Near Beach | Pool

from $1300/Nt
4 4
Details
Stepping Stone has unreal ocean views and a perfect, private stretch of beach. It's pretty secluded, on a quiet end ... Stepping Stone Villa is located along a beautiful beach at the East End of Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1719/Nt
4 4+
Details
Olympus is a modern, beachfront villa with full air-conditioning and an enviable location near Rum Point Beach. Rum Point is ... Has specials. An aerial view of Olympus Villa and the beautiful beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
4 4+
Details
The Penthouse Suite in the Villas at Grace Bay Club is perfect for travelers who want to be as close ... Grace Bay Club Resort pool

Grace Bay, Turks and Caicos

Beachfront | AC

from $5330/Nt
4 4
Details
Vacationing will be as much fun for your kids as it is for you at Sand Castle Villa. It has ... 3 BR rate available.
Has specials. Pool with view of ocean

Anguilla

Beachfront | Pool | AC

from $1700/Nt
4 4+
Details
Infinity is a self-contained island compound ideal for couples or family groups that want some privacy. Your days can be ... 2 & 3 BR rates available. Incredible views from Infinity Villa

St. Thomas, USVI

Pool

from $950/Nt
4 4+
Details
Located right on the French side of St. Martin, Blue Beach Villa is a great beachfront home with tons of ... 2 & 3 BR rates available.
Has specials. Lounge by the pool with amazing ocean views

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

from $929/Nt
4 4
Details
If you are looking for a place to have a couple's get-away or to honeymoon, consider Cadasse Villa. The maid ... 1, 2 & 3 BR rates available. Cadasse Villa has beautiful views and fun area for swimming and relaxing

Cap Estate, St. Lucia

Pool

from $315/Nt
4 4+
Details
Morne Trulah has amazing gardens that are maintained by a team of full-time gardeners. The gardens have herbs, palm trees, ... 2 & 3 BR rates available. Morne Trulah photo

Rodney Bay, St. Lucia

Near Beach | Pool

from $900/Nt
4 4
Details
La Pergola is a favorite of visitors to St. Martin. One recent guest wrote, "The villa and location were beautiful. ... 2 & 3 BR rates available.
Has specials. La Pergola is located in Terres Basses overlooking the Caribbean and Long Bay

Terres Basses (French side), St. Martin

Pool

from $560/Nt
4 4+
Details
With four bedrooms, spacious living areas, and an open floor plan that combines indoor and outdoor living, High Trees Villa ... Has specials. High Trees Villa is located on Gibbs Bay Beach

Barbados

Beachfront | Pool | AC

from $1180/Nt
4 4
Details
Dreamin’ Blue is a great option for families with small children or four couples. The villa has two pools and ... 2 & 3 BR rates available.
Has specials. Dreamin’ Blue is located on a hillside between Happy Bay Beach and Friar’s Bay

Happy Bay (French Side), St. Martin

Near Beach | Pool

from $857/Nt
4 4+
Details
Once you stay at West Bay Club, you'll be planning your return before you even leave. You'll love sitting on ... Has specials. The West Bay Club by night

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2020/Nt
4 4
Details
Great Escape is a great villa rental for a family vacation or special event. Everyone will have plenty of space, ... Has specials. Great Escape Villa is very close to the beautiful beach

Grand Cayman, Cayman

Near Beach | Pool

from $645/Nt
4 3
Details
Ambiance is all that the name implies - a villa with a special atmosphere that will positively impact your entire ... 2 & 3 BR rates available.
Has specials. Ambiance is located in the heart of Terres Basses with access to beautiful beaches nearby

Terres Basses (French side), St. Martin

Pool

from $857/Nt
4 4+
Details
La Percha is ideal for any group of travelers. It has everything you could want in a tropical getaway- four ... Has specials. Lounge by the ocean front pool at La Percha

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

from $1500/Nt
4 4+
Details
Sunspot Villa manages to combine modern architecture with island charm. It can be used for a family gathering or for ... 2 & 3 BR rates available. Sunspot Villa photo

Peter Bay, St. John

Near Beach | Pool

from $1453/Nt
4 4+
Details
If you're looking for something super modern, you've come to the right place. Ani Villa North is a 4-bedroom, 4-bath ... Ani Villa North is a beautiful location for a Caribbean getaway

Anguilla

Pool

from $5100/Nt
4 4+
Details
Hacienda has plenty of space for a large group, and has a great location for exploring the island. It's private, ... 2 & 3 BR rates available.
Has specials. La Hacienda Villa sits on the Terres Basses hillside

Terres Basses (French side), St. Martin

Pool

from $636/Nt
4 3
Details
If you have a large family or party traveling together, La Pinta has a sister villa—La Nina—right next ... 2 & 3 BR rates available.
Has specials. La Pinta is located in the heart of Terres Basses

Terres Basses (French side), St. Martin

Pool

from $486/Nt
4 4
Details
Capturing as much sunshine as possible is easy at Terrasse de Mer. Whether you want to do that on the ... 2 & 3 BR rates available.
Has specials. Terrasse de Mer Villa photo

Terres Basses (French side), St. Martin

Pool

from $814/Nt
4 4
Details
Every room in this villa has breathtaking water views! Whether you're relaxing on the covered deck or creating a light ... 1, 2 & 3 BR rates available.
Has specials. Pool at La Bella Vita

Virgin Grand Estates, St. John

Pool

from $643/Nt
4 4+
Details
When ISLANDS magazine names you 'One of the Top 20 villas in the World', it's always a good sign. It has ... 1, 2 & 3 BR rates available.
Has specials. The beautiful Bird of Paradise Villa

Anguilla

Near Beach | Pool

from $1850/Nt
4 4+
Details
Imagine waking up to a perfect ocean view every morning, walking into a gourmet kitchen for breakfast, and enjoying a ... 2 & 3 BR rates available.
Has specials. Happy Bay Villa is located on the northern coast of the island within walking distance of Friars Bay

Happy Bay (French Side), St. Martin

Near Beach | Pool

from $700/Nt
4 4+
Details
Open rooms and modern furnishing offer the beginnings of a nice vacation. With screened doors and ceiling fans, you can ... Mango Hill is located on the eastern end of St. Croix

St. Croix, USVI

Pool

from $843/Nt
4 4+
Details
Illusion Villa is perfect for a larger family with older children. An on-site tennis court, putting green, and art-decor inspired ... Has specials. Beautiful views from the balcony at Illusion Villa

Barbados

Pool

from $2250/Nt
4 4+
Details
Located in the hills of Terres Basses, Grand Bleu Villa is a new favorite amongst all who visit. Enjoy a ... 2 & 3 BR rates available.
Has specials. Grand Bleu is located on the hillside of Terres Basses

Terres Basses (French side), St. Martin

Near Beach

from $786/Nt
4 4
Details
Few places are quite as tourist-friendly as Barbados, but thanks to the amazing weather, friendly people, and great activities, this ... Capri Manor is located just across the street from Gibbs Beach

Barbados

Near Beach | Pool

from $550/Nt
4 4+
Details
A holiday can be defined by a list of things to do. For others, it's about exquisite beauty. If you're ... 1, 2 & 3 BR rates available. Ana Capri Estate photo

Tortola, BVI, British Virgin Islands

Pool

from $572/Nt
4 4+
Details
Marsh Mellow has incredible views, a spacious layout, and a huge, deep pool. Since the villa is crescent-shaped, every room ... Has specials. Lounge in luxury, poolside at Marsh Mellow Villa

Barbados

Pool

from $1035/Nt
4 4+
Details
Kai Vista is a colorful oceanfront villa that encompasses all that an idyllic, tropical getaway destination should. After long evening ... Has specials. Kai Vista photo

Grand Cayman, Cayman

Beachfront | Pool | AC

from $745/Nt
4 4
Details
This villa is great for a family. Most of the bedrooms are upstairs, and there's terraces on both levels so ... Saving Grace Villa photo

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2300/Nt
4 3
Details
Right on Grace Bay, Sunsara Villa will have you living in the lap of luxury. Everything about this place is ... 3 BR rate available. Sunsara Villa is located on the northern end of Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $2025/Nt
4 4
Details
If you love the ocean, you'll love vacationing at Serenity Now. The villa is a minute from Seven Mile Beach, ... Serenity Now Villa is located in the West Bay area and is steps away from Seven Mile Beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1139/Nt
4 3
Details
Turks and Caicos is well-known as one of the best areas in the Caribbean for beach lovers, and the Venetian ... Has specials. Penthouse at The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $1425/Nt
3 3
Details
This vacation rental is perfect if you want to be in the middle of the action on Grace Bay. It ... The Estate at Grace Bay Club

Grace Bay, Turks and Caicos

Beachfront | AC

from $3700/Nt
3 3+
Details
Sandcastle Beach House is an action-packed choice for your next family vacation, anniversary, or celebration. With kayaks, paddle boards, bikes, ... Has specials. The Sandcastle Beach House is located on a beautiful beach in Limestone Bay

Anguilla

Beachfront | Pool | AC

from $1350/Nt
3 3+
Details
The beautifully landscaped and stylish Saline Reef is a great vacation spot for families with children over 12, or adults who ... 2 BR rate available. Saline Reef sits on the northernmost end of St. Lucia and has a beautiful pool and patio

Cap Estate, St. Lucia

Near Beach | Pool

from $580/Nt
3 3
Details
Tequila Sunrise is a beachfront villa perfect for anyone who wants to have a truly relaxing vacation. It's extremely private, ... 1 & 2 BR rates available.
Has specials. Lounge poolside with amazing views of the ocean

Anguilla

Near Beach | Pool

from $990/Nt
3 3
Details
Villa del Sol's infinity pool and beachfront location make the perfect backdrop for week in the sun. With nearby golf, ... Poolside views of the Caribbean from Villa del Sol

Leeward, Turks and Caicos

Beachfront | Pool | AC

from $1750/Nt
3 3
Details
Gibbes Beach is one of Barbados' nicest white sand beaches on the West Coast. Shops, groceries, and restaurants are only ... Has specials. Plunge pool and gardens leading to the beach at Waverly Villa

Barbados

Beachfront | Pool | AC

from $600/Nt
3 2
Details
Sol e Luna is very private with gardens that surround the house giving guests the option of dressing or not. ... 1 & 2 BR rates available.
Has specials. Sol e Luna is located in the desirable Terres Basses

Terres Basses (French side), St. Martin

Pool

from $521/Nt
3 3
Details
Waterfall Villa can accommodate up to 6 guests within its 3 luxurious bedrooms. Light and open, Waterfall is situated to enjoy island ... 1 & 2 BR rates available.
Has specials. Waterfall Villa is located on a tropical hillside over looking the Caribbean

Rendezvous Bay, St. John

Pool

from $479/Nt
3 3+
Details
Tuscany Resort is one of my favorite properties on Turks and Caicos. At WhereToStay.com, we only list resorts that ... 1 & 2 BR rates available.
Has specials. The Tuscany Resort is located on East Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $775/Nt
3 3
Details
Turks and Caicos is well-known as one of the best areas in the Caribbean for beach lovers, and the Venetian ... 1 & 2 BR rates available.
Has specials. The Venetian photo

Grace Bay, Turks and Caicos

Beachfront | AC

from $875/Nt
3 3+
Details
Any traveler review will tell you that the West Bay Club in Turks and Caicos is one of the best ... Has specials. The West Bay Club from Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1680/Nt
3 3
Details
Want privacy? Like to snorkel? Love to relax? If you answered yes, the Sea Pearl in St. Lucia has what ... 1 BR rate available. Sea Pearl Villa photo

Cap Estate, St. Lucia

Near Beach | Pool

from $415/Nt
2 2
Details
Villa Zatarra is a wonderful find, designed and decorated by a local couple, Rob and Veron. Rob is known on ... Perfect pool - Walk out the door and take a dip!!

Cap Estate, St. Lucia

Pool

from $300/Nt
2 2
Details
Bamboo Villa on St. Martin's French side is a private home featuring 2 bedrooms, 2.5 bathrooms, and much more. The kitchen is ... 1 BR rate available.
Has specials. Bamboo Villa is located less than a mile from Long Bay

Terres Basses (French side), St. Martin

Pool

from $545/Nt
2 2+
Details
At Royal Palms Villa, you can spend a day playing tennis, then return to a gated community knowing that you'll ... 1 BR rate available. Royal Palms Villa photo

St. Croix, USVI

Pool

from $525/Nt
2 2+
Details
Grace Bay Beach is known as the best beach in the world, and this beautiful 2-bedroom condo is just a ... Has specials. Grace Bay Beach along the West Bay Club

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $1020/Nt
2 2
Details
This Rio Mar Luxury 2 bedroom Ocean Villa is for anyone with a need for relaxation and a desire for that ... Rio Mar Beach Resort Luxury Ocean Villa photo

Northeast Coast, Puerto Rico

Beachfront | Pool | AC

from $450/Nt
2 2
Details
Perfect for a couple on a honeymoon or just looking for a great vacation, the 1-bedroom condo at the West ... Has specials. The West Bay Club has a beautiful pool

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

from $630/Nt
1 1
Details

Where To Stay

Home Page
My Trip
My Favorites
Magazine