Jamaica Family Villas


The Caribbean is a great destination choice for families or multiple families traveling together. With a private kitchen and enough space for everyone, a Caribbean villa rental can be the most economical accommodation choice. Whether you are seeking a beachfront villa, a private island or a hillside villa with an amazing view, our favorite family villas section provides some of the best villas in the Caribbean for your family vacation.


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
Super spacious luxury villa with next-level outdoor amenities. 5, 6, 7 & 8 BR rates available. Haystack Villa is located in the prestigious Tryall Club

Montego Bay, Jamaica

Pool

from $2000/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
Live like kings and queens for the duration of your vacation at Tryall Club's Round House Villa Roundhouse Villa has beautiful outdoor spaces

Montego Bay, Jamaica

Pool

from $2143/Nt
Ocean and pool view from back patio

Montego Bay, Jamaica

Pool

from $3143/Nt
Anticipation Villa on Montego Bay: views of the Caribbean Sea and the Tryall Golf Course will vy for your attention Anticipation Villa at Tryall Club photo

Montego Bay, Jamaica

Pool

from $2241/Nt
Your group will love the views - and - the attention to the details The Luxurious pool and back yard area at Rose Cottage

Montego Bay, Jamaica

Pool

from $2338/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
Lovely hillside villa with pool, a full staff, and Tryall Club amenities View of Caribbean

Montego Bay, Jamaica

Pool

from $1429/Nt
Luxury vacationing, Jamaican style There are fabulous ocean views from the porch at Overlook Villa

Montego Bay, Jamaica

Pool

from $1559/Nt
Ocean front villa ideal for families with young children Sunset at the Tryall Club has a beautiful beachfront pool and hot tub

Montego Bay, Jamaica

Beachfront | Pool | AC

from $1949/Nt
Mahogany Hill is for travelers in want of high-class resort accommodations, top-of-the-line luxury and privacy, and plenty of activities to do Lush tropical landscaping and private pool at Mahogany Villa

Montego Bay, Jamaica

Pool

from $1624/Nt
Luxury villa with spacious rooms and a circular layout wrapped around a cobalt tiled pool. Casuarina photo

Montego Bay, Jamaica

Pool

from $1299/Nt
Good times await at Montego Bay Yellowbird Villa photo

Montego Bay, Jamaica

Pool

from $786/Nt
Fully staffed and located within Jamaica’s exclusive and premier Tryall Club Luxurious pool area at Linger Longer Villa

Montego Bay, Jamaica

Pool

from $650/Nt