Jamaica Villa Rentals

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1 Bedroom Jamaica Villas

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A-2 Villa at Tryall Club

Montego Bay, Jamaica

1 Bedroom and 1 Baths
Maximum Guests: 2
Near Beach
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A-2 Villa at Tryall: A relaxing and enjoyable getaway in Jamaica's Georgian Great House
From $393 / Night

3 Bedroom Jamaica Villas

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Linger Longer Villa

Montego Bay, Jamaica

3 Bedrooms and 3 Baths
Maximum Guests: 6
Pool
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Fully staffed and located within Jamaica’s exclusive and premier Tryall Club
From $857 / Night
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Pinnacle Villa at Tryall

Montego Bay, Jamaica

3 Bedrooms and 3 Baths
Maximum Guests: 6
Pool
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Luxurious living with full staff, golfing and spectacular ocean views
From $786 / Night
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Serenity Villa at Tryall Club

Montego Bay, Jamaica

3 Bedrooms and 0 Baths
Maximum Guests: 6
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From $571 / Night
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Sunset Villa at Tryall Club

Montego Bay, Jamaica

3 Bedrooms and 3 Baths
Maximum Guests: 6
Beachfront, Pool
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Ocean front villa ideal for families with young children
From $786 / Night

4 Bedroom Jamaica Villas

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Cielo Villa

Montego Bay, Jamaica

4 Bedrooms and 4 Baths
Maximum Guests: 8
Pool
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Lovely hillside villa with pool, a full staff, and Tryall Club amenities
From $864 / Night
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Coo Yah Villa at Tryall Club

Montego Bay, Jamaica

4 Bedrooms and 4 Baths
Maximum Guests: 8
Pool
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This private 4-bedroom villa located on a golf course comes with a pool, a staff of 5, and tons of amenities
From $864 / Night
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Eve Song

Montego Bay, Jamaica

4 Bedrooms and 4 Baths
Maximum Guests: 8
Pool
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A secluded and relaxing island vacation awaits
From $707 / Night
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Fairwinds at Tryall

Montego Bay, Jamaica

4 Bedrooms and 4 Baths
Maximum Guests: 8
Pool
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An all-encompassing and relaxing Jamaican vacation awaits
From $707 / Night
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Folly Villa at Tryall Club

Montego Bay, Jamaica

4 Bedrooms and 4 Baths
Maximum Guests: 8
Pool
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Dramatic view of the Caribbean Sea with Montego Bay in the distance.
From $707 / Night
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Ma' Moura Villa at Tryall Club

Montego Bay, Jamaica

4 Bedrooms and 4 Baths
Maximum Guests: 8
Pool
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An exceptional choice for those who want a carefree and luxurious Caribbean vacation.
From $707 / Night
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Reef House at Tryall Club

Montego Bay, Jamaica

4 Bedrooms and 4 Baths
Maximum Guests: 8
Beachfront, Pool
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Stunning beachfront property with pool and staff
From $707 / Night
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Seaspray Villa at Tryall Club

Montego Bay, Jamaica

4 Bedrooms and 4 Baths
Maximum Guests: 8
Beachfront, Pool
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Beachfront home with large pool and hot tub
From $864 / Night
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Tradewinds Villa at Tryall Club

Montego Bay, Jamaica

4 Bedrooms and 4 Baths
Maximum Guests: 8
Pool
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Low-key and relaxing villa sits right on the water's edge and comes with its own helpful staff
From $707 / Night
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Yellowbird Villa

Montego Bay, Jamaica

4 Bedrooms and 4 Baths
Maximum Guests: 8
Pool
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Good times await at Montego Bay
From $864 / Night

5 Bedroom Jamaica Villas

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Infinity Villa at Tryall Club

Montego Bay, Jamaica

5 Bedrooms and 6 Baths
Maximum Guests: 12
Pool
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If you don't want to lift a finger on vacation, then the Infinity Villa at Tryall will meet all of…
From $1,929 / Night
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5 Bedrooms and 5 Baths
Maximum Guests: 10
Pool
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From $1,171 / Night
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No le Hace at Tryall Club

Montego Bay, Jamaica

5 Bedrooms and 5 Baths
Maximum Guests: 10
Pool
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The view is unmatched anywhere in Tryall Club!
From $864 / Night
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Overlook Villa

Montego Bay, Jamaica

5 Bedrooms and 5 Baths
Maximum Guests: 10
Pool
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Luxury vacationing, Jamaican style
From $1,429 / Night
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Sundance Villa at Tryall Club

Montego Bay, Jamaica

5 Bedrooms and 5 Baths
Maximum Guests: 10
Pool
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From $1,714 / Night
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Villa Lolita at Tryall Club

Montego Bay, Jamaica

5 Bedrooms and 5 Baths
Maximum Guests: 10
Pool
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From $1,429 / Night

6+ Bedroom Jamaica Villas

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6 Bedrooms and 6 Baths
Maximum Guests: 12
Pool
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Anticipation Villa on Montego Bay: views of the Caribbean Sea and the Tryall Golf Course will vy for your attention
From $1,429 / Night
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6 Bedrooms and 6 Baths
Maximum Guests: 12
Pool
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Spectacular 6-bedroom villa with resort amenities, privacy, views, and plenty of activities
From $1,429 / Night
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Jubilation at Tryall Club

Montego Bay, Jamaica

6 Bedrooms and 7 Baths
Maximum Guests: 14
Pool
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From $1,571 / Night
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Karma Bay at Tryall Club

Montego Bay, Jamaica

6 Bedrooms and 6 Baths
Maximum Guests: 12
Beachfront, Pool
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Huge 6-bedroom villa on the beach has tons of amenities, including a full staff and the use of Jamaica's famed Tryall Club
From $1,429 / Night
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6 Bedrooms and 7 Baths
Maximum Guests: 12
Pool
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If you are a traveler who prefers luxury, then the Rose Cottage Villa at Tryall is the perfect Jamaican retreat.…
From $1,714 / Night
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Twin Palms Villa at Tryall

Montego Bay, Jamaica

6 Bedrooms and 6 Baths
Maximum Guests: 12
Pool
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Twin Palms: Fabulous pool spread out over seven levels will make you feel like you have a resort all to yourself
From $2,857 / Night
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Viviana Villa at Tryall Club

Montego Bay, Jamaica

6 Bedrooms and 6 Baths
Maximum Guests: 12
Pool
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Huge 6-bedroom oceanfront villa has access to a private beach, comes with a full staff, and has tons of extras
From $1,429 / Night
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Windward Villa at Tryall Club

Montego Bay, Jamaica

6 Bedrooms and 6 Baths
Maximum Guests: 12
Pool
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Windward Villa offers fun, sun, and relaxation in a spacious and stunning Jamaican villa
From $1,714 / Night
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Harmony Hill at Tryall

Montego Bay, Jamaica

7 Bedrooms and 7 Baths
Maximum Guests: 14
Beachfront, Pool
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If you are looking for the ultimate Caribbean getaway, then look no further than Harmony Hill at Tryall. Located on…
From $1,857 / Night
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Phoenix Villa at Tryall

Montego Bay, Jamaica

7 Bedrooms and 7 Baths
Maximum Guests: 14
Beachfront, Pool
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Newly renovated Caribbean living is what the Phoenix Villa at Tryall has to offer. With a private beach and pool,…
From $1,429 / Night
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7 Bedrooms and 7 Baths
Maximum Guests: 14
Pool
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From $1,486 / Night
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Sugar Hill at Tryall Club

Montego Bay, Jamaica

7 Bedrooms and 7 Baths
Maximum Guests: 14
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From $1,714 / Night
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Haystack Villa at Tryall Club

Montego Bay, Jamaica

8 Bedrooms and 8 Baths
Maximum Guests: 16
Pool
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Haystack Villa offers you outdoor living at it's best. With a grand pool, game room, pool table and verandah, this…
From $1,714 / Night
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Golden Clouds

Ocho Rios, Jamaica

9 Bedrooms and 9 Baths
Maximum Guests: 20
Pool
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Whether you want to spend your vacation listening to your iPod and reading or play tennis or taking the time…
From $1,143 / Night
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Hanover Grange Villa

Montego Bay, Jamaica

9 Bedrooms and 9 Baths
Maximum Guests: 18
Pool
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From $2,143 / Night
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Silent Waters Villa

Montego Bay, Jamaica

10 Bedrooms and 6 Baths
Maximum Guests: 20
Pool
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Silent Waters Villa is a sprawling villa just outside of Montego Bay that offers everything you could possibly need for…
From $1,883 / Night

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