Collections

Contact Us

Large Groups Villa Collection

Large Groups Villa Collection


Vacation rentals that are large enough to accommodate a group are often hard to come by and renting multiple hotel rooms can break the bank. WhereToStay.com has searched all over the Caribbean to bring you a collection of villas large enough to accommodate groups on their Caribbean vacations. Unlike a hotel, villa rentals provide one cost for the entire home giving everyone their own space while still enjoying various amenities such as a private pool, chef services and housekeeping. Go on, take a look, the perfect villa for your group vacation is sure to be here!


There's really no island quite like Calivigny. This gem was purchased in 2000 by a couple who wanted to create a first-class oasis with every luxury imaginable. They did just that ...
Calivigny Island is located just south of Woburn Bay, Grenada
20 BR rate.

Grenada

Beachfront | Pool | AC

Details
The Pearls of Long Bay are the gems of Providenciales. Each home has a theater-style media room, two pools, tons of outdoor space, and ultra chic decor. The Estate is ...
Pearls of Long Bay Estate

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Emara Estate is a brilliant property located on the exclusive Turtle Tail Peninsula. Formerly owned by Prince, this estate boasts 5 star facilities, private beaches, and is ideal for family gatherings, ...
Emara Estate is located on the Turtle Tail peninsula of Providenciales island

Emara Estate

17 16+

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

Details
Necker Island is the place to go if you want the ultimate privacy, luxury, and pampering. You can rent out the whole island to yourself, or just one room during ...
The Beach pool at Necker Island
Specials.

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

Details
Ever dream of staying on Necker Island but renting the entire island is inconceivable? Well, I have great news for you! Celebration Weeks at Necker Island offer travelers the unique ...
Aerial view of Necker Island
1 BR rate.

Necker Island, BVI, British Virgin Islands

Beachfront | Pool | AC

Details
This private island resort is perfect for a casual, relaxing vacation for any group of travelers. Every activity you can imagine is here, from snorkeling to fishing to kayaking. There's ...
Thatch Caye photo

Thatch Caye

15 15

Belize

Near Beach | AC

Details
Over Yonder Cay is the pinnacle of luxury. It's a private island in the Bahamas with a full staff of expert guides and more sources of entertainment than you can ...
Over Yonder Cay is a spectacular exclusive private island south of Nassau in the Bahamas

Exuma and Cays, Bahamas

Beachfront | Pool | AC

Details
ÀNI Dominican Republic is a property that doesn't skimp on luxury. There's pools with massive water slides, a private beach, kayaks and paddle boards, a full staff, and 14 spacious bedrooms. ...
ÀNI Dominican Republic has an amazing infinity edge pool with Caribbean views
6-13 BR rates.

Cabrera, Dominican Republic

Pool | AC | Resort Villa

Details
Seaclusion Oasis combines two gorgeous properties into one luxurious villa rental. The villas sit on the world’s most beloved beach, Grace Bay, with the now famous turquoise waters and ...
Seaclusion Villa and Seascape Villa combined comprise the Seaclusion Oasis in Grace Bay Beach
Specials.

Grace Bay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
This estate can easily accommodate large groups thanks to thirteen large bedrooms, indoor and outdoor dining areas, and sprawling patios. This villa offers sunset views, is kid-friendly, and is within ...
The stunning infinity pool at Mes Amis Villa overlooks the beauty of Baie Rouge
7-12 BR rates.
Specials.

Mes Amis

13 0

Terres Basses (French side), St. Martin

Pool | AC

Details
Combining the words, "Luxurious" and "All-Inclusive" can almost sound paradoxical. But at Three Bees at Harbour Island, Bahamas these two words go hand in hand. This extraordinary rental property (for ...
Three Bees is located on Harbour Island Bahamas

Harbour Island, Bahamas

Beachfront | Pool

Details
Arrecife 23/24/25 make up a luxurious estate with resort amenities like a full staff, beautiful landscaping, pristine pools, and glamorous design. Each villa has flatscreen TVs, a fully equipped kitchen, and ...
Arrecife 23/24/25 Estate at Punta Cana Resort photo

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Casa Bahia is luxurious, exclusive, and elegant. It has full chef services, two infinity pools, and a full home gym… needless to say, it’s a celebrity favorite! The villa ...
Casa Bahia is located in Casa de Campo directly on Minitas Beach

Casa Bahia

12 11+

Casa de Campo, Dominican Republic

Beachfront | Pool | AC

Details
Laughing Waters is luxurious, exclusive, and secluded without being isolated. This unbelievable resort estate has a full team of staff, multiple villas on property, and every amenity needed for a ...
Laughing Waters is located in Barbados Sandy Lane
Specials.

Barbados

Pool | AC | Resort Villa

Details
Located in the Exuma Islands, Musha Cay at Copperfield Bay has five luxurious homes you can choose from, from the 10,000-square-foot Manor House called Highview, the secluded beach houses (Pier ...
Musha Cay at Copperfield Bay photo
6-11 BR rates.

Musha Cay, Bahamas

Beachfront | Pool | AC

Details
Although Bella Casa is super spacious, it manages to create an intimate atmosphere. You can easily relax with your family and friends or retreat into a quiet space for privacy. ...
La Bella Casa is located in Terres Basses overlooking the La Samanna Hotel and Baie Longue Beach
4-11 BR rates.
Specials.

Terres Basses (French side), St. Martin

Pool | AC

Details
Golden Clouds is one to remember because it has meditation gardens that wind throughout the property, and several spots dedicated to yoga and zen. It doesn't hurt that its right ...
Golden Clouds Villa is located on Jamaica's north coast in the village of Oracabessa
9-11 BR rates.
Specials.

Ocho Rios, Jamaica

Pool | AC

Details
Sanzaru is perfect for a corporate retreat, getaway with friends, or family vacation. There's easy access to the beach, shopping in Holetown, and several restaurants, but there's also loads to ...
Sanzaru photo

Sanzaru

11 11

Barbados

Pool | AC

Details
The Branson Estate offers a private island experience for large groups and families. The estate offers three impressive master suites and eight luxurious guest suites, so everyone can vacation on ...
 Branson Estate is situated at the northeast tip of Moskito Island

Moskito Island, BVI, British Virgin Islands

Beachfront | Pool

Details
Triton Estate, which can be found tucked away amid the unspoiled sand dunes of Long Bay Beach, has established a benchmark for luxury in the Turks and Caicos Islands. Over ...
Triton Estate is located along a beautiful stretch of Long Bay Beach
9, 10 BR rates.
Specials.

Triton Estate

11 10+

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Hawksbill Estate is ideal for hosting staff retreats as well as family get-togethers. The sheer magnitude of it gives the impression that you are hiring your very own hotel. The ...
The Hawksbill Estate is located on a beautiful stretch of Grace Bay Beach

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Sand Dollar Estate is the best bet for a St. Thomas wedding, family reunion, or special occasion. With a full staff, luxury amenities, and panoramic views, this property has everything. ...
Sand Dollar Estate is located in Magen’s Bay with it's own white sandy beach
6, 9 BR rates.

St. Thomas, USVI

Beachfront | Pool | AC

Details
The Residence at COMO Parrot Cay is ideal for any travelers who expect first-rate service and luxury. You’ll be waited on by two personal butlers and a chef, and ...
The Residence at COMO Parrot Cay photo

Parrot Cay, Turks and Caicos

Beachfront | Pool | AC | Resort Villa

Details
If you do things with an all or nothing attitude, you'll flip over Le Bleu Villa. It's hard to think of anything this drop-dead gorgeous rental doesn't have. Aside from ...
Le Bleu Villa its on 2.5 acres of beachfront in Little Harbor
10 BR rate.

Anguilla

Beachfront | Pool | AC

Details
Villa Doma has a gorgeous location right on Babalua Beach. Hang around the beach with the villa’s stand up paddle boards and kayaks, or take the villa's Jeep Wrangler ...
Bella Vita is a contemporary villa located near Babalua Beach
8, 9 BR rates.
Specials.

Villa Doma

10 10+

North Shore, Turks and Caicos

Beachfront | Pool | AC

Details
English Harbour #28 is a great family vacation villa. Six of the bedrooms can be connected to the partnering suite, and there are four buildings on the property with their own ...
English Harbour #28 is located on a hillside overlooking the harbour

English Harbour, Antigua

AC

Details
This beachfront vacation rental is a tranquil, luxurious place to take your family, friends, or wedding party. With ten bedrooms, a resort-worthy pool, and four acres of privacy, it’s ...
Aerial views of the Samsara property and surrounding area

Samsara

10 7+

North Shore, Turks and Caicos

Beachfront | Pool | AC

Details
If you're looking for luxury and elegance in St. Jean, Unik has it in spades. This ten-bedroom villa will make any traveler's jaw drop, with interiors designed by Philippe Starck ...
Unik villa is located in the heights Saint Jean overlooking St. Jean Bay
6, 7 BR rates.

Unik

10 10

Saint Jean, St. Barts

Pool | AC

Details
Punta Aguilla 22 in the Dominican Republic is a dreamy spot. Boasting incredible ocean views, this villa provides an idyllic Caribbean getaway. With its own private pool, you'll be able to ...
Punta Aguila 22 in Casa de Campo Resort

Casa de Campo, Dominican Republic

Pool | AC | Resort Villa

Details
Sole E Mare is a breathtaking beachfront oasis nestled along the pristine shores of Grace Bay. Offering the perfect blend of luxury and natural beauty, Sole E Mare offers direct ...
Sole E Mare Villa on Grace Bay
8 BR rate.

Sole E Mare

10 10+

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Surrounded on three sides by green, tropical foliage, Le Chateau des Palmiers is ideal for any luxury vacation. The villa can sleep eighteen guests, and every detail feels opulent. The ...
Le Chateau des Palmiers is located directly on Plum Bay Beach
6 BR rate.
Specials.

Terres Basses (French side), St. Martin

Beachfront | Pool | AC

Details
Cove Spring offers its guests every amenity they could possibly need or imagine. Guests can give their full attention to lounging by the pool, generating endorphins in the gym, or ...
Cove Spring photo

Cove Spring

10 10+

Barbados

Beachfront | Pool | AC

Details
Imagine having a bonfire on the beach after a long day of fun swimming, playing in the sand, tennis and exploring. That's what you will get at Flor de Cabrera. ...
The luxurious resort like pool is just steps away from the ocean at Flor de Cabrera
Specials.

Cabrera, Dominican Republic

Beachfront | Pool | AC

Details
If you are looking for something private, secluded, and very high-end, then Elsewhere Villa is for you. Ten bedrooms are spread across a large main house, a pool house, and ...
Elsewhere Villa is located in the prestigious Sandy Lane Club area
6, 8 BR rates.

Barbados

Pool | AC

Details
Silent Waters Villa is a sprawling villa just outside of Montego Bay that offers everything you could possibly need for your group vacation, including two swimming pools and a helicopter ...
Aerial View of Silent Waters
3-7 BR rates.
Specials.

Montego Bay, Jamaica

Pool | AC | Resort Villa

Details
The cove on which Crystal Springs Villa rests is like a clip out of a castaway movie. It is private and secluded, and the sugary white sands invite you to ...
Crystal Springs is a beautiful Estate located right on the beach
5-9 BR rates.

Barbados

Beachfront | Pool | AC

Details
For large groups wanting extreme luxury, the oceanfront ÀNI Anguilla is a perfect choice. There are two separate villas, each with their own private pool, common areas, and five-star amenities. ...
ÀNI Anguilla
6-9 BR rates.

ANI Anguilla

10 10

Anguilla

Pool | AC

Details
I recommend Casa Sunshine for family vacations or big celebrations with friends. With 10 bedrooms and three levels of air-conditioned interiors, this villa was made for large parties of travelers. It's ...
Casa Sunshine photo
4-9 BR rates.
Specials.

Guana Bay (Dutch Side), St. Martin

Beachfront | Pool | AC

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

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
Yarari Royale is one of a kind when it comes to luxury. You'll be spoiled by daily housekeeping, full butler service, and a chef for every meal. The cherry on ...
Yarari Royale is a beautiful home located in Cap Cana

Cap Cana, Dominican Republic

Pool | AC | Resort Villa

Details
The Beach House is the biggest and most impressive accommodation on the island. If you want to vacation in style, this house is for you. There's 9 suites, a freeform pool, ...
The Beach House at Calivigny Island
7 BR rate.

Grenada

Beachfront | Pool | AC | Resort Villa

Details
La Dolce Vita is super luxurious and spacious. There's seven different lounges inside the villa and tons around the property's exterior. Expect only the chicest decor and most glamorous amenities. ...
La Dolce Vita photo
Specials.

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
One Perfect Day is a well-equipped, charming villa. It has a five-star kitchen with tons of appliances, massive outdoor space, and equally tricked-out bedrooms. Each suite opens to the terrace ...
One Perfect Day Villa is located on the Peterborg Peninsula overlooking Magens Bay

St. Thomas, USVI

Near Beach | Pool | AC

Details
This villa has all the luxury and amenities you'd expect in a five-star Caribbean villa. The floor plans are open and ocean-facing, and there's nine bedrooms to spare. There's even ...
La Palmeraie is located on Harbour Island in the Bahamas

Harbour Island, Bahamas

Beachfront | Pool | AC

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 feet water frontage and provides a massive two-level waterfront terrace ...
Salacia Villa in Grace Bay offers amazing amenities
7 BR rate.

Salacia

9 9+

Grace Bay, Turks and Caicos

Near Beach | Pool | AC

Details
This ultra-modern villa is a great choice for any multi-generational family vacation. It's golf course location keeps kids a few minutes from the beach, and the villa's pool is above ...
Luxury pool and golf course views

Punta Cana, Dominican Republic

Pool | AC | Resort Villa

Details
If you’re looking for luxury, Nevaeh has it in abundance. Not only does it sit on a gorgeous, private piece of Long Bay, it also has 1.35 acres of lush, ...
Nevaeh is located on a beautiful stretch of Long Bay Beach
5-8 BR rates.

Anguilla

Beachfront | Pool | AC

Details
Kiko has a great location that truly can't be beat. It's in Paynes Bay on Barbados's Platinum Coast, which is home to most of the island's restaurants, bars, and activities. ...
Villa Kiko is located on Payne's Bay
6, 8 BR rates.

Kiko

9 9+

Barbados

Beachfront | Pool | AC

Details
The Oasis Estate has it all - luxury, privacy, and exclusivity. This four-story, nine-bedroom villa is on an island that has a status as one of the most exclusive private ...
The Oasis Estate is a sleek and contemporary tropical hideaway perched on the island’s peak

Moskito Island, BVI, British Virgin Islands

Pool | AC

Details
If you're wanting to vacation in a quiet, luxurious, beachfront villa, La Palmeraie is perfect! This villa is huge - encompassing nine bedrooms, nine and a half baths, and 12,000 square ...
La Palmeraie - Villa 2 is located in Triana Shores on Harbour Island

Harbour Island, Bahamas

Beachfront | AC

Details
Rip Kai is a magnificent, oceanfront estate perfect for your next Grand Cayman vacation. It's prepared to handle families celebrating milestone events with luxury and privacy, or your next unforgettable ...
Rip Kai Villa in Rum Point
Specials.

Grand Cayman, Cayman

Beachfront | Pool | AC

Details
Emara West is a stunning villa that manages to blend the perfect balance between privacy and resort like experiences. It has amazing views over the ocean, and plenty of entertainment ...
Emara West Villa is located on the Turtle Tail peninsula of Providenciales island

Turtle Tail, Turks and Caicos

Beachfront | Pool | AC

Details
Situated on the shores of Sapodilla Bay in Chalk Sound, La Mer South is a picture-perfect vacation spot fit for the whole family. A private dock with over the water ...
Le Mer Villa South is located on Sapodilla Bay in Chalk Sound

Taylor Bay-Sapodilla Bay, Turks and Caicos

Pool | AC

Details
Capri Villa is the perfect venue for your next birthday, anniversary, wedding, or retreat. The villa is in Cap Estate, a luxurious community that’s home to St. Lucia’s ...
Capri Villa photo
5-8 BR rates.

Cap Estate, St. Lucia

Near Beach | Pool | AC

Details
"Cerulean" means "heaven," and this private resort attends to all the details of your stay to create your personal heaven. A full staff with butlers, a general manager, a culinary ...
Cerulean Villa is located on Barnes Bay

Anguilla

Beachfront | Pool | AC

Details
Sitting directly on Long Bay Beach, Casa Varnishkes is an opulent, gated estate perfect for families or larger group gatherings. With nine bedrooms, a large swimming pool, fitness room, and ...
 Casa Varnishkes is located on a beautiful stretch pf Long Bay Beach
6 BR rate.
Specials.

Long Bay, Turks and Caicos

Beachfront | Pool | AC

Details
Santosha sits right on Long Bay Beach and is perfect for beach weddings, anniversaries, and any special event. You can't help but feel like you're at a resort here, since ...
Santosha is located along a beautiful stretch of Long Bay Beach
5-8 BR rates.

Anguilla

Beachfront | Pool | AC

Details
“Nevaeh” is “heaven” backwards, and the villa's golf simulator, movie theater, media room, and gym are just a few of the reasons why this celestial name suits the property. The ...
Nevaeh is located on a beautiful stretch of Long Bay Beach
5-8 BR rates.

Anguilla

Beachfront | Pool | AC

Details
Impulse is honestly one of a kind. There's sculptures and statues throughout the space, waves of colored lights in the ceiling, and wraparound ocean views. There are four huge Master ...
Expansive living area has endless views of the ocean
4, 7 BR rates.

Grace Bay, Turks and Caicos

Beachfront | Pool | AC

Details
This two-story home is ideal for families to share or for a few couples. The bedrooms are spread out over both levels, and there's tons of space outside to relax. ...
La Serena Villa features a private dock that brings you to a beautiful private sandy beach

La Serena

8 6+

Punta Cana, Dominican Republic

Beachfront | Pool | AC | Resort Villa

Details

Where To Stay

 

Main Menu