Cayman Group Villas

Cayman Group Villas


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!


Coconut Walk was designed to maximize views and luxury. You can see the ocean from almost everywhere in the house, ... Has specials. Coconut Walk Villa at twilight

Grand Cayman, Cayman

Beachfront | Pool | AC

from $4450/Nt
Southern Ayr is a large, family-friendly home. You can walk to the Silver Thatch Welcome Center and The Lighthouse Restaurant ... Has specials. Southern Ayr is located on the southeastern coast

Grand Cayman, Cayman

from $950/Nt
You'll never lack entertainment here at Fischer's Reef. Have a cornhole tournament by the pool, read in the gazebo, or ... Has specials. Fischer's Reef Villa is located right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1950/Nt
Our Cayman Cottage is pretty impressive. This villa was made for family reunions, with ample space for kids and adults ... Has specials. Our Cayman Cottage sits along a beautiful stretch of  beach on the north side of Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1195/Nt
Evolution is going to revolutionize your next family vacation. Not only is there a specific children's bedroom, but there's also ... Evolution Vill offers it all - right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
Tatenda is a great family villa because its far enough from cruise traffic and tourist spots to actually relax, but ... Tatenda Villa is a beautiful beach front home just along South Sound

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2139/Nt
This luxury villa is absolutely beautiful and has plenty of room for any group. The outdoor space is amazing, with ... The pool and beautiful beach at Kaia Kamina

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2859/Nt
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
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
Cayman Castle is impressive to say the least. It can accommodate up to 16 people, has a private beach, and tons ... 5 BR rate available.
Has specials.
Spectacular views, infinity edge pool and oceanfront lounging await at Cayman Castle

Grand Cayman, Cayman

Near Beach | Pool

from $995/Nt
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 $2500/Nt
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
Kempa Kai is luxurious, gorgeous, and unforgettable. Its modern design is both beautiful and practical, while the exterior is packed ... Kempa Kai villa is located on a nature preserve near Rum Point

Grand Cayman, Cayman

Beachfront | AC

from $3149/Nt
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
Facing the impressive coast of the Caribbean Sea in Rum Point, Moon Kai Villa has six bedrooms that provide you ... Has specials. Moon Kai has a beachfront pool where you can lounge in the Caribbean sun

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1950/Nt
When you drive up to this grand villa, you feel as though you are at your own mini hotel. The ... Has specials. Far Tortuga Villa is on the north side of Grand Cayman, on the way to Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $700/Nt
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
Hidden Cove is perfect if you love being on the water and want a bit of privacy. It's near great ... Has specials. An aerial view of Hidden Cove Villa - it is located just adjacent to the Bio-luminescent Bay

Grand Cayman, Cayman

Near Beach | Pool

from $600/Nt
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
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
Great Bluff Estate is perfect for groups who want privacy and space. It's fully gated, and sits on the quiet, ... Has specials. Great Bluff Estates sits along the beautiful northern coast of Grand cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $995/Nt
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
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
This villa has a great open floor plan and sits on picturesque Cayman Kai. The high ceilings, minimal design, and ... Has specials. Ocean Kai sits directly on the beach near Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $925/Nt
This beachfront villa in Rum Point has tons of outdoor activities, from volleyball to snorkeling to swimming. For air-conditioned activities, ... Has specials. Sea Grape Villa sits just on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $525/Nt
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
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
In Harmony is a charming beachfront villa that would be perfect for your next family vacation. It has a private ... An aerial view of in Harmony Villa located directly on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1139/Nt
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
This villa has an amazing private beach that's perfectly set up for parties and al fresco feasts. The bedrooms are ... Has specials. The private pool at Kai Zen is tucked away to the side of the villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $575/Nt

Where To Stay

Home Page
My Trip
My Favorites
Magazine