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!


Luxury oceanfront property with seven bedrooms, water-sports equipment, and access to Seven Mile Beach. Has specials. Coconut Walk Villa at twilight

Grand Cayman, Cayman

Beachfront | Pool | AC

from $5000/Nt
The perfect villa for a family vacation, with a multi-level terrace, huge rooms, and eight bedrooms spread out over two floors. Fischer\'s Reef Villa is located right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1950/Nt
This villa was made for family vacations, with four levels and ample lounging space. 6 BR rate available.
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 $1200/Nt
Open, chic beachfront villa with a family-friendly design. Has specials. Evolution Vill offers it all - right on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2300/Nt
This villa was designed to maximize privacy and relaxation, with three levels of suites and a separate apartment. Has specials. Tatenda Villa is a beautiful beach front home just along South Sound

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2300/Nt
Beautiful, well-designed villa with amazing outdoor space. Has specials. The pool and beautiful beach at Kaia Kamina

Grand Cayman, Cayman

Beachfront | Pool | AC

from $3100/Nt
Beachfront villa great for families and groups, with entertainment for kids and adults alike. Coral Reef Villa is situated directly on Seven Mile Beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2860/Nt
Six bedroom oceanfront property with a protective coral reef 6 BR rate available.
Has specials.
Twin Palms Villa - the namesake beautiful palm trees

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1500/Nt
18-guest villa with oceanfront privacy, 75-foot pool, and space for everyone. 5 & 6 BR rates available.
Has specials.
Aerial view of Villa Mora

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1600/Nt
Oceanfront villa with private beach access, total seclusion, and unique architecture. Has specials. Spectacular views, infinity edge pool and oceanfront lounging await at Cayman Castle

Grand Cayman, Cayman

Near Beach | Pool

from $1750/Nt
Breathtaking ocean view from the pool, with private secluded beach just steps away 5 & 6 BR rates available.
Has specials.
The beautiful Crystal Blue Villa is perched on a cliffside just off Queens Highway

Grand Cayman, Cayman

Pool

from $950/Nt
Fully-equipped large group villa with several family-friendly suites and lots of outdoor space. Has specials. Beachfront pool at Oceanus Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2300/Nt
Family-friendly villa with a bunk room, huge Great Room, outdoor amenities, and an ideal location in Rum Point. Has specials. The perfect image for Sun Salutations Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2700/Nt
Six-bedroom seaside villa with private courtyard and large entertainment area 5 BR rate available.
Has specials.
Moon Kai has a beachfront pool where you can lounge in the Caribbean sun

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2225/Nt
Grand and spacious ocean front property with some of the best snorkeling on the island 4 & 5 BR rates available. Far Tortuga Villa is on the north side of Grand Cayman, on the way to Rum Point

Grand Cayman, Cayman

Beachfront | Pool | AC

from $750/Nt
A private Grand Cayman estate with tranquil design and a Master Suite that feels like a spa. Has specials. Tranquility Cove Villa has a luxurious infinity edge pool

Grand Cayman, Cayman

Beachfront | Pool | AC

from $2300/Nt
Fully air-conditioned villa right on the water, with kayaks and bicycles to take to Rum Point Beach. 4 BR rate available. An aerial view of Hidden Cove Villa - it is located just adjacent to the Bio-luminescent Bay

Grand Cayman, Cayman

Near Beach | Pool

from $700/Nt
Two story, beachfront villa with spacious rooms and a large balcony. 4 & 5 BR rates available.
Has specials.
Amarone Villa is a luxurious home on the South Coast

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1550/Nt
South Sound Beach villa with five star amenities and no shortage of entertainment. Has specials. Point of View Villa is located on a picturesque Caribbean beachfront

Grand Cayman, Cayman

Beachfront | Pool | AC

from $3100/Nt
Gated two-story estate with three levels of outdoor space and chic amenities. Great Bluff Estates sits along the beautiful northern coast of Grand cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1425/Nt
5 bedroom secluded villa with pool, hot tub and room to breathe 4 BR rate available. Ecstasea has a beautiful pool and patio area with the ocean in the background

Grand Cayman, Cayman

Beachfront | Pool | AC

from $850/Nt
Relax in this villa's infinity pool, beach cabana and hammock and enjoy the close proximity to George Town Has specials. Lounge poolside on the beach at Pease Bay House

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1950/Nt
Beachfront island home with plenty of room for family getaways 4 BR rate available. The pool and this cabana are located right on the beach at Reef Romance Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $950/Nt
Spacious, minimalistic beachfront villa with a loft for kids and a central living area. 4 BR rate available.
Has specials.
Ocean Kai sits directly on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1200/Nt
Fully air-conditioned villa with tons of outdoor activities and a beach in the backyard. Sea Grape Villa sits just on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $700/Nt
Spacious, beachfront villa with a boat dock and spacious floor plans. Right on the beach with a dock leading to a gazebo Faroway is an ideal Cayman destination

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1275/Nt
Super private beachfront villa with water sports, a home theater, and ocean views. Has specials. Stepping Stone Villa is located along a beautiful beach at the East End of Grand Cayman

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1900/Nt
Kayaks, hammocks, screened porches, and a boat dock makes this fully air-conditioned villa perfect for sun-lovers. 3 BR rate available. Great Escape Villa is very close to the beautiful beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $750/Nt
Family-friendly villa with a bunk room for kids, a kayak, and a great location between Rum Point and Seven Mile Beach. 3 BR rate available. An aerial view of Present Moment Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $650/Nt
Beachfront villa with its own strip of sand, an oceanfront pool, and lots of windows. Has specials. An aerial view of in Harmony Villa located directly on the beach

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1100/Nt
Oceanfront villa near snorkeling reefs, Seven Mile Beach, and marine life. Has specials. Lounge on the deck with amazing ocean views at Serenity Now Villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $1275/Nt
Private villa within a resort neighborhood with a private beach and walking distance to yacht clubs. Has specials. The private pool at Kai Zen is tucked away to the side of the villa

Grand Cayman, Cayman

Beachfront | Pool | AC

from $750/Nt
Traditional Caribbean villa with full air-conditioning and a home theater. Has specials. A aerial view of Casuarina Cove shows the dock into the water

Grand Cayman, Cayman

Beachfront | AC

from $550/Nt