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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
Prepare for the ultimate escape at Bayview Estate in vibrant Mykonos! With twenty bedrooms, two stunning pools, and epic views, it's a paradise for large groups. Get ready for beach-hopping, ...
Bayview Estate photo

Mykonos, Greece

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
Experience the epitome of luxury at The Yellow House in Menorca. With its iconic architecture and lavish interiors, indulge in tranquility and sophistication. Nestled amidst lush forest, enjoy exclusive access ...
The Yellow House photo

Balearic Islands, Spain

Near Beach | Pool

Details
Embark on an adventure at Domaine de la Drome! This enchanting estate offers a tapestry of scenic wonders. Explore the medieval charm of Crest, and indulge in the estate's three ...
Domaine de la Drome photo

Provence, France

Pool

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
The Temple Guiting Estate stands as a beacon of elegance and tranquility in the heart of the Cotswolds
The Estate photo

The Estate

15 13

England, United Kingdom

Pool | AC

Details
Hawkswood Country Estate, near St Andrews, is a luxurious retreat set in picturesque Peat Inn. With 15 bedrooms across three properties, it's perfect for groups. Indulge in hydro spas, short-game areas, ...
Hawkswood Country Estate photo

Scotland, United Kingdom

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
Escape to Villa Jessica, a lavish duo of villas in Crete! With fourteen bedrooms for twenty-eight guests, enjoy poolside bliss, beach jaunts, and gourmet delights. Perfect for parties or peaceful ...
Jessica photo

Jessica

14 16

Crete, Greece

Near Beach | Pool | AC

Details
A distinguished frontline beach estate on Marbella's Golden Mile, blending classical Andalusian architecture with Western influences inspired by Frank Lloyd Wright. Surrounded by manicured gardens adorned with contemporary art, Villa ...
Villa Murillo photo

Marbella, Spain

Near Beach | Pool | AC

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
A luxurious Mykonos escape where every detail spells extravagance! With thirteen opulent bedrooms, three infinity pools overlooking the shimmering Aegean Sea, and a slew of top-notch amenities, get set for ...
Mermaid Cove photo

Mermaid Cove

13 15

Cyclades, Greece

Pool | AC

Details
Discover Villa on The Cliff in Sardinia. With five suites boasting stunning sea views, this renovated retreat offers ultimate luxury. Enjoy private pools, gourmet dining, and Italian craftsmanship in every ...
Villa on the Cliff in Sardina

Sardinia, Italy

Near Beach | Pool | AC

Details
Indulge in the epitome of luxury at the enchanting Cigno estate on the mesmerizing shores of Lake Como! With two opulent villas offering breathtaking views, private pools to splash in, ...
Cigno Estate

Cigno

13 13

Italian Lakes, Italy

Pool

Details
Explore Dun Aluinn, Scotland's premier Design Led Exclusive Use venue. With luxurious accommodations and exquisite dining, it's a haven of elegance. The restored Victorian home boasts opulent interiors and breathtaking ...
Dun Aluinn photo

Dun Aluinn

13 13

Scotland, United Kingdom

Details
Stucktaymore in Perthshire is the perfect place for the whole family. Kids will love the games room and you can keep them entertained for hours! When the sun goes down, ...
Stucktaymore photo

Stucktaymore

13 13

Scotland, United Kingdom

Details
Perched high in Cannes California, Villa Bleu Cristal is a modern marvel with breathtaking views. Luxurious amenities, stunning gardens, a sparkling pool and a tennis court make it the ultimate ...
Villa Bleu Cristal photo

Cannes, France

Pool | AC

Details
Chateau des Lumieres: where an 11th-century marvel meets modern luxury. Picture breathtaking views, a private heated pool, and stylish interiors that redefine elegance. It's not just a chateau; it's a ...
Chateau des Lumieres photo

Cote d'Azur, France

Pool

Details
Discover Castello Niccone, an enchanted haven where history meets modern luxury. This 500-year-old estate, meticulously renovated, offers five distinct houses filled with light and classical elegance. Immerse yourself in the ...
Castello Niccone photo

Umbria, Italy

Pool | AC

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 13+

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

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
Experience grandeur at Villa Alava, an opulent retreat for up to 24 guests. With 11 stylish bedrooms, expansive lounges, and lavish amenities, including indoor and outdoor pools, a bar, and cinema room, ...
Villa Alava photo

Villa Alava

12 12

Marbella, Spain

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
Discover Vigna del Chianti, a lavish Tuscan estate set amid oak forests and vineyards. With three charming dwellings, a lush garden, and a panoramic pool, it's the ultimate retreat for ...
Vigna del Chianti Villa

Tuscany, Italy

Pool | AC

Details
Indulge in the ultimate beachfront escape at the luxurious Timeless Paradise Villa. With breathtaking views, an infinity pool, and 11 bedrooms, this one-of-a-kind property is perfect for large groups and families. ...
Timeless Paradise Villa in Rum Point

Rum Point, Cayman

Beachfront | Pool | AC

Details
La Ferme des Vignes is a Provencal paradise near Valreas. Dive into luxury amidst vineyards and truffle-rich forests. This farmhouse flawlessly blends authentic and contemporary styles. Ideal for family holidays, ...
La Ferme des Vignes photo

Provence, France

Pool | AC

Details
Natural Beauty As a travel pro, let me tell you about Le 5 Perle di Lucca in Italy. It's a gem of a property that's oozing with charm and character. The ...
Le 5 Perle di Lucca photo

Tuscany, Italy

Pool

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
Unveil the magic of Tosca Estate in Val D'Orcia! A cinematic journey along Cypress-lined paths leads to a historic blend of farmhouse and renaissance villa. Stunning wine cellar, panoramic views, ...
Tosca Estate photo

Tosca Estate

11 11

Tuscany, Italy

Pool | AC

Details
Experience luxury at Mas de Lacoste. With stunning views, six lavish bedrooms, and a renovated winery, it's the ultimate retreat. Enjoy alfresco dining, a sparkling pool, and endless amenities for ...
Mas de Lacoste photo

France

Pool | AC

Details
Experience the essence of Mediterranean living at La Finca, a transformed manor house in Llucmayor surrounded by vineyards. This holiday villa offers relaxation, hammocks, and an oversized pool. With ten ...
La Finca photo
10 BR rate.

La Finca

11 10

Balearic Islands, Spain

Pool | AC

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
Escape to Villa Maiori, a dazzling retreat on the Amalfi Coast! Tucked amid lush greenery and lemon groves, this luxurious haven boasts contemporary cottages perched on cliffs, offering breathtaking sea ...
Villa Maiori photo

Villa Maiori

11 11

Amalfi Coast, Italy

Near Beach | Pool | AC

Details
A restored Menorcan farmhouse amidst lush countryside. With a spacious pool and 150 hectares of wildland, it's your sanctuary. This stylish villa offers 11 bedrooms across three levels, each exuding unique charm. ...
Finca Benedicta photo

Balearic Islands, Spain

Pool

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
Nestled atop a hill overlooking Cannes, Mandelieu, and the Esterel mountains, this extraordinary property offers unparalleled luxury and history. Originally a monastery, transformed by famed architect Sir Edwin Lutyens, this ...
Chateau Charlene overlooks the bay of Cannes

Cannes, France

Pool | AC

Details
Dive into the artistic splendor of Chateau des Arts, an 18th-century gem in Calanques de Cassis National Park. With ten lavish bedrooms, a private heated pool, and a vibrant art ...
Chateau des Arts photo

Provence, France

Pool

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

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