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

Calivigny Island - Estate

Grenada

Beachfront | Pool | AC

25 25
Details
Necker Island is the place to go if you want the ultimate privacy, luxury, and pampering. You can rent out ... Has specials. The Beach pool at Necker Island

Necker Island

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

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

Thatch Caye

Belize

Near Beach

15 15
Details
Over Yonder Cay is the pinnacle of luxury. It's a private island in the Bahamas with a full staff of ... Over Yonder Cay is a spectacular exclusive private island south of Nassau in the Bahamas

Over Yonder Cay - A Private Island

Exuma and Cays, Bahamas

Beachfront | Pool | AC

15 12
Details
Ani Villa Estate - Dominican Republic is a property that doesn't skimp on luxury. There's pools with massive water slides, ... 6, 7, 8, 9, 10, 11, 12 & 13 BR rates available. Ani Villa Estate in The Dominican Republic has an amazing infinity edge pool with Caribbean views

Ani Villa Estate - Dominican Republic

Cabrera, Dominican Republic

Pool

14 14
Details
This estate can easily accommodate large groups thanks to fourteen large bedrooms, indoor and outdoor dining areas, and sprawling patios. ... 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

Mes Amis

Terres Basses (French side), St. Martin

Pool

14 14+
Details
Combining the words, "Luxurious" and "All-Inclusive" can almost sound paradoxical. But at Three Bees at Harbour Island, Bahamas these two ... Three Bees is located on Harbour Island Bahamas

Three Bees at Harbour Island

Harbour Island, Bahamas

Beachfront | Pool | AC

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 is located in Terres Basses overlooking the La Samanna Hotel and Baie Longue Beach

La Bella Casa

Terres Basses (French side), St. Martin

Pool

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. Golden Clouds Villa is located on Jamaica's north coast in the village of Oracabessa

Golden Clouds

Ocho Rios, Jamaica

Pool

12 12
Details
If you do things with an all or nothing attitude, you'll flip over Le Bleu Villa. It's hard to think ... 10 BR rate available. Le Bleu Villa its on 2.5 acres of beachfront in Little Harbor

Le Bleu Villa

Anguilla

Beachfront | Pool | AC

11 11
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

Calivigny Island - The Beach House

Grenada

Beachfront | Pool | AC

10 10
Details
This beachfront vacation rental is a tranquil, luxurious place to take your family, friends, or wedding party. With ten bedrooms, ... Aerial views of the Samsara property and surrounding area

Samsara

North Shore, Turks and Caicos

Beachfront | Pool | AC

10 7+
Details
If you want a lot of room to roam around in, water access, a full staff, and luxury accommodations, Indigo ... Indigo Villa is located right on Little Harbor and has its on little piece of sandy beach

Indigo Villa

Anguilla

Beachfront | Pool | AC

10 10
Details
Surrounded on three sides by green, tropical foliage, Le Chateau des Palmiers is ideal for any luxury vacation. The villa ... 6 BR rate available.
Has specials. Le Chateau des Palmiers is located directly on Plum Bay Beach

Le Chateau des Palmiers

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

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

Flor de Cabrera

Cabrera, Dominican Republic

Beachfront | Pool | AC

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

Elsewhere Villa

Barbados

Pool

10 10
Details
Silent Waters Villa is a sprawling villa just outside of Montego Bay that offers everything you could possibly need for ... 3, 4, 5 & 7 BR rates available. Aerial View of Silent Waters

Silent Waters Villa

Montego Bay, Jamaica

Pool

10 6
Details
For large groups wanting extreme luxury, the oceanfront Ani Villa Estate is a perfect choice. There are two separate villas, ... 4, 6, 7, 8 & 9 BR rates available. Ani Estate Anguilla - North and South

Ani Villa Estate - Anguilla

Anguilla

Pool

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

Casa Sunshine

Guana Bay (Dutch Side), St. Martin

Beachfront | Pool | AC

10 10
Details
Villa Arrecife 24/25 is located in the gated community of La Cana Resort & Club

Villa Arrecife 24/25

Punta Cana, Dominican Republic

Pool

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

One Perfect Day

St. Thomas, USVI

Near Beach | Pool

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, 7 & 8 BR rates available. Nevaeh is located on a beautiful stretch of Long Bay Beach

Nevaeh Villa - Fully Staffed

Anguilla

Beachfront | Pool | AC

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

Capri Villa

Cap Estate, St. Lucia

Near Beach | Pool

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.
Has specials. Casa Varnishkes is located on a beautiful stretch pf Long Bay Beach

Casa Varnishkes Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

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

Aliseo Villa

Barbados

Pool

9 10+
Details
“Nevaeh” is “heaven” backwards, and the villa's golf simulator, movie theater, media room, and gym are just a few of ... 5, 6, 7 & 8 BR rates available. Nevaeh is located on a beautiful stretch of Long Bay Beach

Nevaeh Villa

Anguilla

Beachfront | Pool | AC

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

Coconut Walk

Grand Cayman, Cayman

Beachfront | Pool | AC

8 6+
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

La Serena

Punta Cana, Dominican Republic

Beachfront | Pool | AC

8 6+
Details
Kandara is great if you're looking for space and privacy. The villa and guest house has 10,000 square feet of space, ... 6 BR rate available. Kandara Villa is located on Anguilla's West End

Kandara

Anguilla

Near Beach | Pool

8 8+
Details
Coconut Walk is a gorgeous choice for a group vacation. The villa is modern, elegant, and well-designed for large parties. ... Coconut Walk is an oceanfront estate on Seven Mile Beach

Coconut Walk - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

8 7+
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

Belair Great House

Barbados

Near Beach | Pool

8 6
Details
Nelson Gay House’s design, staff, and location are all the ingredients you need for an incredible vacation. The crystal ... 4, 5, 6 & 7 BR rates available.
Has specials. Nelson Gay House is located on Godings Beach and has beautiful gardens

Nelson Gay House

Barbados

Beachfront | Pool | AC

8 8+
Details
Your trip to the Dominican Republic should be nothing short of quiet and relaxing, and Casa Kimball will help redefine ... Casa Kimball is located on the north coast of the island of the Dominican Republic

Casa Kimball

Cabrera, Dominican Republic

Near Beach | Pool

8 8
Details
Mullins Mill is truly where the living is easy. With a full staff to anticipate your every desire, you'll have ... 4 & 6 BR rates available.
Has specials. There is a beautiful ridge side pool at Mullins Mill

Mullins Mill

Barbados

Pool

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

Sunrise Villa

Cabrera, Dominican Republic

Beachfront | Pool | AC

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

The Beach House

Anguilla

Beachfront | Pool | AC

8 9+
Details
Tucked behind the pristine sand dunes of Long Bay Beach, Triton Villa has set a new standard for luxury in ... Triton Villa is located along a beautiful stretch of Long Bay Beach

Triton Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

7 6+
Details
Sand & Sea offers tons of ways to have fun in the sun. Not only does it sit directly between Grace ... 5 BR rate available. Sand & Sea Villa sits just on the canal a short walk to the very end of Grace Bay Beach

Sand and Sea

Leeward, Turks and Caicos

Near Beach | Pool

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 is located on incredible beach frontage on Gun Bay

Cayman Castle and Guesthouse - Platinum

Grand Cayman, Cayman

Near Beach | Pool

7 7+
Details
Twin Palms really stands out, and not just for its unique ocean view. The beach is silky soft, has great ... Twin Palms is located near Rum Point on a beautiful stretch of ocean

Twin Palms - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

7 5
Details
If you want a beachfront villa with private bedrooms, a generous lap pool, and amazing snorkeling, Mora is a great ... Villa Mora is located on a beautiful beachfront in South Sound

Mora - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

7 7
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

Zenaida Beach & Tennis Estate

Anguilla

Beachfront | Pool | AC

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 ... 4 & 5 BR rates available. Paradise Villa is located near Blowing Point

Paradise Villa

Anguilla

Pool

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

La Koubba Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

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. Vieux Caribe Villa is located near Taylor Bay Beach

Vieux Caribe Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

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 BR rate available. Tamarind Villa is located in Windward Hills views are of both the Atlantic Ocean and the Caribbean

Tamarind Villa

Cap Estate, St. Lucia

Pool

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

Fustic House

Barbados

Near Beach | Pool

7 7
Details
Monte Bay Villa is an attractive getaway with a master suite that will make you want to spend your entire ... Monte Bay Villa sits atop a hillside just above Monte Bay

Monte Bay Villa

Klein Bay, St. John

Near Beach | Pool

7 6+
Details
Le Caprice is designed for days of sunbathing and unwinding. The large pool is surrounded by a sprawling sundeck, and ... 4, 5 & 6 BR rates available.
Has specials. Le Caprice Villa is located on a hilltop above Baie Rouge in Terres Basses

Le Caprice Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

7 6
Details
This is a fantastic property for large families or groups that are working within a budget. There is plenty of ... Twin Palms Villa - the namesake beautiful palm trees

Twin Palms Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

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 ... Villa Mora is located beachfront in South Sound

Villa Mora

Grand Cayman, Cayman

Beachfront | Pool | AC

7 7+
Details
Cayman Castle has plenty of opportunity for fun! It has access to a beach, tons of room outside to take ... Cayman Castle is located on incredible beach frontage on Gun Bay

Cayman Castle

Grand Cayman, Cayman

Near Beach | Pool

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 is located on Seven Mile Beach

Seascape Villa

Grand Cayman, Cayman

Beachfront | AC

7 5
Details
Jamoon is the place to be for family reunions, couples getaways, and girls trips. Kids and adults alike love the ... 3, 4, 5 & 6 BR rates available.
Has specials. Private resort style pool and outdoor entertainment area at Jamoon

Jamoon - Sandy Lane

Barbados

Pool

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

La Maison Michelle Villa

Barbados

Pool

7 7+
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

Harmon Estate

Costa Rica

Pool

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 a hillside overlooking Guana Bay

Amalia

Guana Bay (Dutch Side), St. Martin

Near Beach | Pool

6 7
Details
If you’re looking for all the comforts of home with a gorgeous tropical setting, Amarone is the place to ... Amarone Villa is located on South Sound Road with a beautiful stretch of white sand beach

Amarone - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

6 6+
Details
There's something for everyone at Sea Star! Kick back in the infinity pool and gaze out at the sea, walk ... Sea Star Villa is located on Cabrita Point

Sea Star

St. Thomas, USVI

Beachfront | Pool | AC

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

Chateau Margot Villa

Bordeaux, St. John

Pool

6 5+
Details
This is a great place to combine work and play. There's every amenity you could want, from a fully equipped ... Sol y Sombra Villa is located on a hillside just above Little Trunk Bay

Sol y Sombra

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

6 6+
Details
Baraka Point has a ton of privacy and great beach access. You can snorkel around the reef right outside the ... 3 BR rate available.
Has specials. Baraka Point is an amazing Villa Estate on the western Coast of Virgin Gorda

Baraka Point

Virgin Gorda, BVI, British Virgin Islands

Beachfront | Pool | AC

6 6+
Details
This luxurious, beachfront villa has everything you need for an unforgettable vacation. L’Oasis gives guests instant access to the ... 4 & 5 BR rates available.
Has specials. L'Oasis Villa is located at the far end of Baie Rouge Beach

L'Oasis Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

6 7
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

La Salamandre

Terres Basses (French side), St. Martin

Near Beach | Pool

6 6
Details
An infinity pool at La Josephine Villa sets the tone of the whole vacation. It makes visitors feel as if ... 5 BR rate available.
Has specials. La Josephine Villa is located near La Samanna and overlooks Baie Longue

La Josephine

Terres Basses (French side), St. Martin

Near Beach | Pool

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 is on a hillside overlooking Plum Bay

Cascades Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

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 BR rate available. Colibri Cottage sits on a hill above Soufriere Bay

Colibri Cottage

Soufriere, St. Lucia

Near Beach | Pool

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

Maison de Reve Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

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 is located hillside on the exclusive Rendezvous Bay overlooking the south shore

Mare Blu Villa

Rendezvous Bay, St. John

Pool

6 8
Details
One thing everyone who stays at Akasha mentions is the gorgeous view. It’s absolutely breathtaking! The villa is well-designed ... 1, 2, 3, 4 & 5 BR rates available. Akasha Villa is located in Cap Estate and offers views of the Piton Mountains and Pigeon Island

Akasha Villa

Cap Estate, St. Lucia

Pool

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

Little Whale Cay

Berry Islands, Bahamas

Pool

6 6
Details
Antilles Pearl is a super luxurious beachfront villa in one of the best spots on Anguilla. There's a 50-foot skywalk ... 5 BR rate available.
Has specials. Antilles Pearl is located on Shoal Bay Beach

Antilles Pearl Villa at Altamer

Anguilla

Beachfront | Pool | AC

6 6
Details
Sandyline Villa is one of the most luxurious estates on St. Martin. The exterior amenities are endless, and the villa’... 3, 4 & 5 BR rates available.
Has specials. Plenty of loungers surround the swimming pool

Sandyline Villa

Terres Basses (French side), St. Martin

Near Beach | Pool

6 7
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

Vistamar Villa

Barbados

Pool

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

Royal Belize - Private Island

Belize

Beachfront | AC

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

Sun Salutations Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

6 5+
Details
Deja View is perfect for any special event. With five master suites and a bunk room, there's no shortage of ... Deja View is located above Rendezvous Bay on the southern side of St. John

Deja View

Gifft Hill, St. John

6 6+
Details
Kishti Villa on Meads East is a spacious and extravagant beachfront property on one of the best beaches in the ... Kishti Villa East on Meads Bay offers relaxing outdoor spaces

Kishti Villa on Meads East

Anguilla

Beachfront | Pool | AC

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 is located on the beautiful beach of Plum Bay in the Terres Basses gated community

C'est La Vie Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

6 6
Details
Mandalay Villa’s design, features, and amenities will make you feel like royalty the instant you arrive. This 5-bedroom beach ... The palatial pool area

Mandalay Villa

Long Bay, Turks and Caicos

Beachfront | Pool | AC

6 7+
Details
The best thing about this villa is easily the location. It's right on South Sound Beach, which is calm and ... Amarone Villa is a luxurious home on the South Coast

Amarone Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

6 7
Details
Tortuga Bay C-17 Villa is located in Punta Cana

Tortuga Bay C-17

Punta Cana, Dominican Republic

Near Beach | Pool

6 6+
Details
Trou Rolland has everything you could want in a Caribbean villa: amazing views, beach proximity, and a great location. You’... 3 BR rate available. Trou Rolland is located on a hillside overlooking Marigot Bay

Trou Rolland Villa

Marigot Bay, St. Lucia

Near Beach | Pool

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

Point of View Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

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

Gwynt A Mor Villa

North Shore, Turks and Caicos

Pool

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. The pool and view of the ocean from Beach Enclave Ocean View Villas

Beach Enclave Ocean View Villas North Shore

North Shore, Turks and Caicos

Beachfront | Pool | AC

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

Crystal Waters

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4
Details
Magens Hideaway is located on the Peterborg Peninsula overlooking Great Hans Lollick and the BVI's

Magens Hideaway

St. Thomas, USVI

Pool

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

The Beach House

St. Thomas, USVI

Beachfront | AC

5 4+
Details
The Five Bedroom Beach Level residences are perfect for families or four couples to share. They're right on Grace Bay ... Has specials. The Grace Bay Club Estate

Grace Bay Club Estate Five Bedroom Beach Level Pool Residence

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

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

Casa de la Playa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

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

Three Dolphins

Anguilla

Near Beach | Pool

5 4+
Details
Dunes 2 by Grace Bay Resorts is an easy, breezy way to relax in luxury in Turks and Caicos. This villa ... Has specials. Dunes 2 Villa (Turtle Inlet) on Grace Bay

Dunes 2

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

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 ... Has specials. The Residences are located directly on Grace Bay Beachfront and each have private infinity pools

Residence 3

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

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

Cos Kai - Platinum

Grand Cayman, Cayman

Beachfront | AC

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

Crystal Waters - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4
Details
Avanti is absolutely gorgeous inside and out. Everywhere you look, the furnishings, decor, and amenities are modern, elegant, and chic. ... Has specials. Avanti is located in Terres Basses just minutes from the beaches on the French Side

Avanti

Terres Basses (French side), St. Martin

Pool

5 5+
Details
Blue Water is the place to be for large groups. There are five bedrooms that can all accommodate couples, although ... Blue Water Villa is located on Rum Point Drive on a beautiful stretch of white sand beach

Blue Water - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4+
Details
Pease Bay House is a luxurious, gorgeous villa that’s totally equipped for your next beachfront vacation. A large part ... Pease Bay House sits along a secluded sandy beach in Bodden Town

Pease Bay House - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

5 5+
Details
Two Rainbows is a fantastic choice for your next family vacation if you want total relaxation. This villa is on ... Two Rainbows is located within walking distance to the Rum Point Club

Two Rainbows - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4+
Details
Rotunda is a great, family-friendly villa rental with gorgeous views and privacy. It’s elevated above Peter and Trunk Bay, ... Rotunda Villa is located above Peter Bay and Trunk Bay

Rotunda

Peter Bay, St. John

Pool

5 5+
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. Sand Castle Villa is located on the North Shore of Anguilla with views of the Atlantic Ocean

Sand Castle Villa

Anguilla

Beachfront | Pool | AC

5 5+
Details
Casa Bougainvillea is the ideal spot for guests who love water sports and beach combing. Situated right on the water's ... Casa Bougainvillea Villa has a beautiful private pool

Casa Bougainvillea Villa

St. Thomas, USVI

Beachfront | Pool | AC

5 4
Details
Paraiso Azul is a comfortable, family-friendly villa perfect for large groups. Its huge deck, living room, and kitchen are well ... Paraiso Azul is located in Monte and overlooks Rendezvous Bay

Paraiso Azul

Rendezvous Bay, St. John

Pool

5 5+
Details
Your Caribbean vacation will be something special when you stay at the beautiful Wild Orchid villa. The house itself is ... Wild Orchid Villa photo

Wild Orchid Villa

Cap Estate, St. Lucia

Near Beach | Pool

5 4
Details
Looking for luxury in St. Martin? Pamplemousse is a great choice - it’s elegant, spacious, and convenient to a ... 3 & 4 BR rates available.
Has specials. Pamplemousse is located in Terres Basses on a cliffside with views looking toward the Caribbean

Pamplemousse Villa

Terres Basses (French side), St. Martin

Pool

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

Mer Soleil Villa

Terres Basses (French side), St. Martin

Pool

5 5
Details
You won’t want to get out of your lounger when you’re at La Siesta. This villa has crazy ... 3 BR rate available.
Has specials. La Siesta is located in Terres Basses looking out toward the island of Anguilla, the Bay of Marigot

La Siesta

Terres Basses (French side), St. Martin

Near Beach | Pool

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

Dene Court - Sandy Lane

Barbados

Pool

5 5+
Details
This is a five bedroom home known by guests as the perfect find for those who want a private vacation ... Two Rainbows is located in the Rum Point area of Grand Cayman

Two Rainbows Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4+
Details
Point of View Villa is a five-bedroom villa in the heart of the Sandy Lane Estate. Thanks to its central ... 4 BR rate available.
Has specials. Point of View Villa has an extremely large pool and surround to enjoy the Caribbean sun

Point of View Villa

Barbados

Near Beach | Pool

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

Belle Fontaine Villa

Terres Basses (French side), St. Martin

Pool

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 property

Alizee Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Beachfront | Pool | AC

5 5
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

Saramanda Villa - Sandy Lane

Barbados

Pool

5 5
Details
If you love the outdoors and want that feeling even when you're indoors, Ashiana Villa is a place you must ... 3 BR rate available. Ashiana Villa photo

Ashiana Villa

Marigot Bay, St. Lucia

Pool

5 4
Details
Coco de Mer is a great choice for big groups who want to soak up St. John’s beaches and ... Coco de Mer at Peter Bay photo

Coco de Mer at Peter Bay

Peter Bay, St. John

Near Beach | Pool

5 6+
Details
Decaj Villa is a great retreat for a family with young children, or two families for that matter. You'll love ... Decaj Villa is located in Cap Estate with views of the ocean in the distance

Decaj Villa

Cap Estate, St. Lucia

Pool

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

Pease Bay House

Grand Cayman, Cayman

Beachfront | Pool | AC

5 5+
Details
Blue Diamond's beachfront luxury leaves nothing out. There's a sound system, WiFi, and air-conditioning throughout the villa, a bar, a ... Has specials. Blue Diamond Villa at Altamer is set on a prestigious location on Shoal Bay

Blue Diamond Villa at Altamer

Anguilla

Beachfront | Pool | AC

5 7
Details
The Beach House is truly a property with something for everyone. You might want to try some rock climbing on ... The Beach House sits on Mail Bay

The Beach House

St. Thomas, USVI

Beachfront | AC

5 3+
Details
Belle Etoile is luxurious inside and out. This wedding-friendly villa has a massive freeform pool, two Jacuzzis, five suites with ... Has specials. Belle Etoile is located in Terres Basses with amazing ocean views

Belle Etoile Villa

Terres Basses (French side), St. Martin

Pool

5 5+
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

Champagne Shores

Anguilla

Near Beach | Pool

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

Tom Tom Villa

Barbados

Pool

5 5+
Details
Kalorama Villa is fabulously unique! This artsy villa mixes contemporary style with such items as the island's traditional, native stone. ... 3 & 4 BR rates available. Kalorama Villa is located in Virgin Grand Estates

Kalorama Villa

Virgin Grand Estates, St. John

Pool

5 4+
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 is located at the base of the Piton mountain range on Beau Estate

Arc En Ciel Villa

Soufriere, St. Lucia

Near Beach | Pool

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

Beaches Edge

Anguilla

Near Beach | Pool

5 5+
Details
Cayman Sands is a great family vacation villa for peace and quiet. There are two children's bedrooms, two master bedrooms, ... Cayman Sands is located in Old Man Bay along a beautiful stretch of white sandy beach

Cayman Sands

Grand Cayman, Cayman

Beachfront | Pool | AC

5 5
Details
This is the perfect location to bring the family together. The house is spacious and inviting. There are five bedrooms ... Reef Romance Villa has an ideal oceanfront location on Rum Point

Reef Romance Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

5 5
Details
Love the beach, but craving privacy? Blue Water is an excellent choice. The big draws to Blue Water are its ... Blue Water has a great beach front location in Rum Point

Blue Water

Grand Cayman, Cayman

Beachfront | Pool | AC

5 4+
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

Nandana Villa

Grand Bahama Island, Bahamas

Pool

5 6
Details
If you want an oceanfront property that is as deluxe as it is spacious, then Kishti Villa on Meads Bay ... Relax in the pool and hot tub during your stay at Kishti Villa West

Kishti Villa on Meads West

Anguilla

Beachfront | Pool | AC

5 6+
Details
This two-story villa has great sunsets over the water, and is near popular Rum Point. There’s floor to ceiling ... Cos Kai is located on a beautiful beach near Rum Point

Cos Kai

Grand Cayman, Cayman

Beachfront | AC

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 ... Has specials. Dunes 1 Villa - (Sundog) Villa is located on Grace Bay

Dunes 1

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

5 5+
Details
Marea is so secluded, it feels like you found your own private island. You can get here by land, sea, ... Marea Villa photo

Marea Villa

Rendezvous Bay, St. John

Near Beach

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. Beach Enclave Beachfront Villas offer amazing ocean views

Beach Enclave Beach Front Villas North Shore

North Shore, Turks and Caicos

Beachfront | Pool | AC

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

Turquoise

Grace Bay, Turks and Caicos

Near Beach | Pool

4 4
Details
Olympus is a modern, beachfront villa with full air-conditioning and an enviable location near Rum Point Beach. Rum Point is ... An aerial view of Olympus Villa and the beautiful beachfront

Olympus

Grand Cayman, Cayman

Beachfront | Pool | AC

4 4+
Details
The Penthouse Suite in the Villas at Grace Bay Club is perfect for travelers who want to be as close ... Has specials. Grace Bay Club Resort pool

Grace Bay Club Penthouse Suite in the Villas

Grace Bay, Turks and Caicos

Beachfront | AC

4 4
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

Sandcastle Beach House

Anguilla

Beachfront | Pool | AC

4 4+
Details
Residence 2 lets you enjoy the convenience of a resort community and the comforts of home, in one villa. The villa ... Has specials. The Residences are located directly on Grace Bay Beachfront and each have private infinity pools

Residence 2

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

4 5+
Details
Kai Vista is a charming beachfront villa for couples or families with older kids. It’s a short walk to ... Kai Vista is located in Rum Point along the north coast

Kai Vista - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

4 4
Details
Olympus has it all: a beachfront location, modern design, and tons of space to lounge. Whether you want to relax ... Olympus is located on the beach front in Rum Point

Olympus - Platinum

Grand Cayman, Cayman

Beachfront | Pool | AC

4 4+
Details
Located right on the French side of St. Martin, Blue Beach Villa is a great beachfront home with tons of ... Has specials. Lounge by the pool with amazing ocean views

Blue Beach Villa

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

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 ... 2 & 3 BR rates available. Cadasse Villa is located on a hilltop with in a gated community in Cap Estate

Cadasse Villa

Cap Estate, St. Lucia

Pool

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

Dreamin Blue

Happy Bay (French Side), St. Martin

Near Beach | Pool

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

West Bay Club - Oceanfront Luxury 4 Bedroom

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

4 4
Details
Great Escape is a great villa rental for a family vacation or special event. Everyone will have plenty of space, ... Great Escape Villa is located on the Rum Point end of the island with a beautiful stretch of beach

Great Escape Villa

Grand Cayman, Cayman

Near Beach | Pool

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

Ambiance Villa

Terres Basses (French side), St. Martin

Pool

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. La Percha Villa is ideally located on the beautiful Taylor Bay

La Percha Villa

Taylor Bay/Sapodilla Bay, Turks and Caicos

Near Beach | Pool

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

La Hacienda Villa

Terres Basses (French side), St. Martin

Pool

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

La Pinta

Terres Basses (French side), St. Martin

Pool

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

Terrasse de Mer Villa

Terres Basses (French side), St. Martin

Pool

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. La Bella Vita Villa sits on a lush hillside overlooking Great Cruz Bay

La Bella Vita Villa

Virgin Grand Estates, St. John

Pool

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. The beautiful Bird of Paradise Villa

Bird of Paradise Villa

Anguilla

Near Beach | Pool

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 Villa

Happy Bay (French Side), St. Martin

Near Beach | Pool

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

Mango Hill Greathouse

St. Croix, USVI

Pool

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

Illusion Villa At Sugar Hill

Barbados

Pool

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

Grand Bleu Villa

Terres Basses (French side), St. Martin

Near Beach

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

Capri Manor

Barbados

Near Beach | Pool

4 4+
Details
If you want a tropical escape, Ana Capri fits the bill. It has amazing views, gorgeous Italian design, and lush ... 1, 2 & 3 BR rates available. Ana Capri Estate photo

Ana Capri Estate

Tortola, BVI, British Virgin Islands

Pool

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. Marsh Mellow Villa is located in Westmoreland in Barbados and has great views of the ocean

Marsh Mellow Villa

Barbados

Pool

4 4+
Details
Kai Vista is a colorful oceanfront villa that encompasses all that an idyllic, tropical getaway destination should. After long evening ... Kai Vista photo

Kai Vista

Grand Cayman, Cayman

Beachfront | Pool | AC

4 4
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

Penthouse at The Venetian

Grace Bay, Turks and Caicos

Beachfront | AC

3 3
Details
Has specials. Grace Bay 3 Bedroom Suite photo

Grace Bay 3 Bedroom Suite

Grace Bay, Turks and Caicos

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

Saline Reef Villa

Cap Estate, St. Lucia

Near Beach | Pool

3 3
Details
This villa has one of the best views in St. Martin! The ocean and sunsets stretch across the horizon as ... 1 & 2 BR rates available.
Has specials. Fields of Ambrosia is located on a hillside in Terres Basses with views of Simpsons Bay Lagoon

Fields of Ambrosia Villa

Terres Basses (French side), St. Martin

Pool

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

Waverly One

Barbados

Beachfront | Pool | AC

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

Sol e Luna Villa

Terres Basses (French side), St. Martin

Pool

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. Waterfall Villa is located on a tropical hillside over looking the Caribbean

Waterfall Villa

Rendezvous Bay, St. John

Pool

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

Tuscany

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

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

The Venetian

Grace Bay, Turks and Caicos

Beachfront | AC

3 3+
Details
West Bay Club has one of the best locations on Turks and Caicos, just behind Grace Bay Beach. A short, ... The West Bay Club from Grace Bay Beach

West Bay Club - Oceanfront Premier 3 Bedroom

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

3 3
Details
Want privacy? Like to snorkel? Love to relax? If you answered yes, the Sea Pearl in St. Lucia has what ... Sea Pearl Villa photo

Sea Pearl Villa

Cap Estate, St. Lucia

Near Beach | Pool

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!!

Villa Zatarra

Cap Estate, St. Lucia

Pool

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 ... Has specials. Bamboo Villa is located less than a mile from Long Bay

Bamboo Villa

Terres Basses (French side), St. Martin

Pool

2 2+
Details

Where To Stay

Home Page
My Trip
My Favorites
Magazine