Jamaica 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!


Six acre estate with beachfront access to coral reefs, on-site sports courts, and two freshwater pools. 5, 6, 7, 8, 9, 10 & 11 BR rates available. Lounge by the pool at Golden Clouds

Ocho Rios, Jamaica

Pool

from $1343/Nt
An impressive pool and terrace winds throughout this luxury villa. 5, 6 & 9 BR rates available.
Has specials.
Aerial View of Silent Waters

Montego Bay, Jamaica

Pool

from $2320/Nt
One of the largest villas at Tryall Club, with a basketball court, game room, and playground. 9 BR rate available. Create Abundance photo

Montego Bay, Jamaica

Pool

from $3391/Nt
Resort style luxury at Hanover Grange

Montego Bay, Jamaica

Pool

from $3052/Nt
Enjoy amazing sunsets on the balcony at Sugar Hill

Montego Bay, Jamaica

Pool

from $2857/Nt
Ocean and pool view from back patio

Montego Bay, Jamaica

Pool

from $3143/Nt
Huge 6-bedroom villa on the beach has tons of amenities, including a full staff and the use of Jamaica's famed Tryall Club Lounge just steps away from the ocean - by the pool at Karma Bay Villa

Montego Bay, Jamaica

Pool

from $2143/Nt
Huge 6-bedroom oceanfront villa has access to a private beach, comes with a full staff, and has tons of extras Annabella Villa Estate located at the Tryall Club

Montego Bay, Jamaica

Pool

from $1714/Nt
Spectacular 6-bedroom villa with resort amenities, privacy, views, and plenty of activities Following Seas Villa at Tryall Club photo

Montego Bay, Jamaica

Pool

from $2273/Nt
Windward Villa offers fun, sun, and relaxation in a spacious and stunning Jamaican villa Windward Villa at Tryall Club photo

Montego Bay, Jamaica

Near Beach | Pool

from $1624/Nt
Lounge by the pool in the Jamaican sun at Retreat villa

Montego Bay, Jamaica

Near Beach | Pool

from $714/Nt
The view is unmatched anywhere in Tryall Club! No Le Hace is a beautiful villa over looking the ocean from the Tryall club

Montego Bay, Jamaica

Pool

from $1429/Nt
Opulent villa with a full staff and luxurious decor. Infinity Villa at Tryall Club photo

Montego Bay, Jamaica

Pool

from $2091/Nt
Lovely hillside villa with pool, a full staff, and Tryall Club amenities View of Caribbean

Montego Bay, Jamaica

Pool

from $1429/Nt
Lush surrounding and tropical vistas at Villa Lolita

Montego Bay, Jamaica

Pool

from $1949/Nt