Jamaica Vacation Rentals

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Cliffside Cottage
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Perched on a lush, green hillside above the Caribbean, Cliffside Cottage has stunning views of Montego Bay.

5 Bedrooms
5 Bathrooms
3 Guides
$857 / night (excl. fees & taxes)
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Afimi - Lagoons
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Four Bedroom, Beachfront Villa in Upscale Lagoons Area

4 Bedrooms
4½ Bathrooms
3 Guides
$1040 / night (excl. fees & taxes)
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Endless Summer - Spring Farm
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One of the most glamorous villas in Jamaica, Endless Summer is a turreted mansion with breathtaking views of the Caribbean Sea.

7 Bedrooms
7 Bathrooms
3 Guides
$1657 / night (excl. fees & taxes)
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Mount Pleasant
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Mount Pleasant is one of Jamaica's most elegant Jamaican mansions

5 Bedrooms
5 Bathrooms
3 Guides
$1307 / night (excl. fees & taxes)
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Drambuie Estate
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Built in the 1940's by the Duke of Marlborough, Drambuie beckons back to old Jamaica when conversation was entertainment and impeccable, discreet serv

5 Bedrooms
5 Bathrooms
3 Guides
$1000 / night (excl. fees & taxes)
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Belle Abri
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Luxurious 12,000 ft² Villa in Spring Farm overlooking Half Moon & the Caribbean

7 Bedrooms
7 Bathrooms
3 Guides
$2286 / night (excl. fees & taxes)
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Emerald Seas
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Two miles east of Ocho Rios, on an elevated hillside near the Prospect Plantation, sits Emerald Seas Villa - 6000 ft² of elegance and luxury.

5 Bedrooms
5 Bathrooms
3 Guides
$857 / night (excl. fees & taxes)
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Vista del Mar - Tryall Club
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Vista Del Mar sits on the top of Barnes Hill and has an majestic alley of palms leading up to this villa at the top of Tryall.

4 Bedrooms
4 Bathrooms
3 Guides
$786 / night (excl. fees & taxes)
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Summerland - Round Hill
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Summerland is a fully staffed private home sited for its dramatic view over the sea. The view is simply mesmerizing day and night

4 Bedrooms
4 Bathrooms
3 Guides
$857 / night (excl. fees & taxes)
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Summerhill
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9 Bedrooms 10,000 sqft Luxury overlooking Half Moon Bay

9 Bedrooms
9 Bathrooms
3 Guides
$1671 / night (excl. fees & taxes)
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Villa Lolita - Tryall
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Villa Lolita is Tryall's newest and most fabulously equipped luxury villa!

5 Bedrooms
5 Bathrooms
3 Guides
$1298 / night (excl. fees & taxes)
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Knockando - Round Hill
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More than 50 years ago, a visionary named John Pringle dreamed of turning a magical Jamaican hillside and waterfront into a luxurious retreat and he n

5 Bedrooms
5½ Bathrooms
3 Guides
$1257 / night (excl. fees & taxes)
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Goat Hill - Montego Bay
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Goat Hill sits on a remarkable site, located specifically to benefit from the spectacular view of the Caribbean Sea

3 Bedrooms
3 Bathrooms
3 Guides
$1000 / night (excl. fees & taxes)
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Golden Clouds
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Golden Clouds villa is a luxurious 12-suite estate situated in a park-like 7-acre setting

10 Bedrooms
10 Bathrooms
3 Guides
$2142 / night (excl. fees & taxes)
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Four Winds
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Experience the five-star side of Jamaica at Four Winds

5 Bedrooms
4 Bathrooms
3 Guides
$1571 / night (excl. fees & taxes)
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Janus - Round Hill
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Located at the highest point on one of the largest individual tracts of land on Round Hill, Janus is one of the most stylish additions to this collect

4 Bedrooms
4 Bathrooms
3 Guides
$2071 / night (excl. fees & taxes)
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Great River
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Set on five acres of gently sloping land with sea view and surrounded by manicured lawns, today's Great River House is the product of a massive renova

5 Bedrooms
5 Bathrooms
3 Guides
$1286 / night (excl. fees & taxes)
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Caribbean Jewel
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Caribbean Jewel is an exquisite villa privately located on Spring farm with magnificent views of the Caribbean sea.

4 Bedrooms
4 Bathrooms
3 Guides
$1043 / night (excl. fees & taxes)
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Allamanda - Great River
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Brand New 8,000ft² private 5 Bedroom, 5 Bathroom villa on 2 acres. Perfect for families

5 Bedrooms
4½ Bathrooms
3 Guides
$1286 / night (excl. fees & taxes)
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Lime Acres
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Lime Acre is a beautiful and unique 3 bedroom, 3.5 bathroom beachfront villa with separate 2 bedroom cottage located in Whitehouse on Jamaica’s tran

5 Bedrooms
4 Bathrooms
3 Guides
$1336 / night (excl. fees & taxes)
    21 – 40 Rentals