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 Golden Clouds, Jamaica villa

Ocho Rios, Jamaica

Pool

From
$1343/Nt
Haystack Villa offers you outdoor living at it's best. With a grand pool, game room, pool table and verandah, this ... 5, 6, 7 & 8 BR rates available Haystack Villa at Tryall Club, Jamaica villa

Montego Bay, Jamaica

Pool

From
$2000/Nt
Hanover Grange Villa, Jamaica villa

Montego Bay, Jamaica

Pool

From
$3052/Nt
Sugar Hill at Tryall Club, Jamaica villa

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 6 & 7 BR rates available Round House Villa at Tryall Club, Jamaica villa

Montego Bay, Jamaica

Pool

From
$2143/Nt
Hummingbird House, Jamaica villa

Montego Bay, Jamaica

Pool

From
$3143/Nt
Silent Waters Villa is a sprawling villa just outside of Montego Bay that offers everything you could possibly need for ... 5 BR rates available Silent Waters Villa, Jamaica villa

Montego Bay, Jamaica

Pool

From
$2320/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, Jamaica villa

Montego Bay, Jamaica

Pool

From
$1949/Nt
Your group will love the views - and - the attention to the details Rose Cottage Villa at Tryall Club, Jamaica villa

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 Karma Bay at Tryall Club, Jamaica 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 at Tryall Club, Jamaica villa

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, Jamaica villa

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, Jamaica villa

Montego Bay, Jamaica

Near Beach | Pool

From
$1624/Nt
Retreat Villa at Tryall Club, Jamaica villa

Montego Bay, Jamaica

Near Beach | Pool

From
$714/Nt
Lovely hillside villa with pool, a full staff, and Tryall Club amenities 4 BR rates available Cielo Villa, Jamaica villa

Montego Bay, Jamaica

Pool

From
$786/Nt
Luxury vacationing, Jamaican style Overlook Villa, Jamaica villa

Montego Bay, Jamaica

Pool

From
$1559/Nt
Ocean front villa ideal for families with young children Sunset Villa at Tryall Club, Jamaica villa

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 Mahogany Hill Villa at Tryall Club, Jamaica villa

Montego Bay, Jamaica

Pool

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

Montego Bay, Jamaica

Pool

From
$1299/Nt
Good times await at Montego Bay Yellowbird Villa, Jamaica villa

Montego Bay, Jamaica

Pool

From
$786/Nt
A secluded and relaxing island vacation awaits Eve Song, Jamaica villa

Montego Bay, Jamaica

Pool

From
$707/Nt
Fully staffed and located within Jamaica’s exclusive and premier Tryall Club Linger Longer Villa, Jamaica villa

Montego Bay, Jamaica

Pool

From
$650/Nt