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!


The perfect villa for a family vacation, with a multi-level terrace, huge rooms, and eight bedrooms spread out over two floors.

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$2100/Nt
Luxury oceanfront property with seven bedrooms, water-sports equipment, and access to Seven Mile Beach. Offers Specials.

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$5000/Nt
This villa was made for family vacations, with four levels and ample lounging space. 6 BR rates available

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$900/Nt
Open, chic beachfront villa with a family-friendly design.

Grand Cayman, Cayman

Beachfront | Pool | AC

Call for rates
Beachfront villa great for families and groups, with entertainment for kids and adults alike.

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$2860/Nt
Six bedroom oceanfront property with a protective coral reef Offers Specials. 6 BR rates available

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$1500/Nt
18-guest villa with oceanfront privacy, 75-foot pool, and space for everyone. Offers Specials. 5 & 6 BR rates available

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$1600/Nt
Oceanfront villa with private beach access, total seclusion, and unique architecture. Offers Specials.

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$1750/Nt
Breathtaking ocean view from the pool, with private secluded beach just steps away Offers Specials. 5 & 6 BR rates available

Grand Cayman, Cayman

Pool

From
$950/Nt
Fully-equipped large group villa with several family-friendly suites and lots of outdoor space.

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$3262/Nt
Media room, beach access, and outdoor dining

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$3105/Nt
Six-bedroom seaside villa with private courtyard and large entertainment area Offers Specials. 5 BR rates available

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$2300/Nt
Grand and spacious ocean front property with some of the best snorkeling on the island Offers Specials. 4 & 5 BR rates available

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$845/Nt
A private Grand Cayman estate with tranquil design and a Master Suite that feels like a spa.

Grand Cayman, Cayman

Beachfront | Pool | AC

Call for rates
Fully air-conditioned villa right on the water, with kayaks and bicycles to take to Rum Point Beach. Offers Specials. 4 BR rates available

Grand Cayman, Cayman

Near Beach | Pool

From
$700/Nt
Two story, beachfront villa with spacious rooms and a large balcony. Offers Specials. 4 & 5 BR rates available

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$1550/Nt
5 bedroom secluded villa with pool, hot tub and room to breathe Offers Specials. 4 BR rates available

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 Offers Specials.

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$1950/Nt
Beachfront island home with plenty of room for family getaways Offers Specials. 4 BR rates available

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$950/Nt
Spacious, minimalistic beachfront villa with a loft for kids and a central living area. Offers Specials. 4 BR rates available

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$1200/Nt
Fully air-conditioned villa with tons of outdoor activities and a beach in the backyard.

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$700/Nt
Spacious, beachfront villa with a boat dock and spacious floor plans.

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$1200/Nt
Super private beachfront villa with water sports, a home theater, and ocean views.

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$3262/Nt
Kayaks, hammocks, screened porches, and a boat dock makes this fully air-conditioned villa perfect for sun-lovers. Offers Specials. 3 BR rates available

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$750/Nt
Family-friendly villa with a bunk room for kids, kayaks, and a great location between Rum Point and Seven Mile Beach.

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$1683/Nt
Private villa within a resort neighborhood with a private beach and walking distance to yacht clubs. Offers Specials.

Grand Cayman, Cayman

Beachfront | Pool | AC

From
$750/Nt
Traditional Caribbean villa with full air-conditioning and a home theater. Offers Specials.

Grand Cayman, Cayman

Beachfront | AC

From
$550/Nt