Jamaica Villas with Pool
1—10 of 75 Villas
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Seafore Jamaica
4 bedroom villa in Tryall from $358 to $1,786 USD per night
Seafore, a 4-bedroom 3,000-square-foot private villa sits on a beautiful private acre at the famous Tryall Club, 60 yards off the 16th fairway.
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Clandestino at The Caves Jamaica
4 bed / 4 bath villa in Negril from $420 to $1,865 USD per night
Nestled in a lush tropical jungle within The Caves' resort property, the approximately 3,500 sq. feet wood, stone and thatched-roofed luxury Caribbean villa, Clandestino, is set on a half acre of naturally landscaped gardens, with magnificent trees, cut stone walkways, and a two-car open-air private parking area.
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Almond Hill Jamaica
4 bedroom villa in Montego Bay from $429 to $993 USD per night
Designed by Prince Kasimir Korybut in 1993 and brilliantly renovated in 2012, Almond Hill is a lovely private home located on a former 500-acre coconut plantation just 22 minutes west of Montego Bay and one minute from posh Round Hill where guests enjoy complimentary resort membership.
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Sea Haven Jamaica
4 bedroom villa in Discovery Bay from $429 to $715 USD per night
Located on a private waterfront acre, Sea Haven is a traditional 4 bedroom West Indian cottage dressed in charming periwinkle blue.
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Calypso Jamaica
4 bedroom villa in Tryall from $497 to $1,786 USD per night
Calypso is a charming open-air 4 bedroom villa adjacent to the 16th fairway of the championship Tryall Golf Course.
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Wild Orchid Jamaica
5 bedroom villa in Montego Bay from $500 to $858 USD per night
On 220 private acres of former banana and coconut plantation stretching from mountain to sea, Wild Orchid is a glamorous and luxurious 5 bedroom hideaway in the tropics.
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Windsong Jamaica
4 bedroom villa in Montego Bay from $500 to $1,143 USD per night
Windsong is an exquisite and very private home four minutes from Round Hill.
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Faithwalk Jamaica
2 bedroom villa in Tryall from $519 to $1,349 USD per night
This enchanting 2 bedroom villa is built around a swimming pool and a tropical vine covered veranda.
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The Cottages at Goldeneye Jamaica
3 bedroom villa in Montego Bay from $560 to $1,440 USD per night
GoldenEye overlooks the Caribbean Sea in the quiet village of Oracabessa Bay on Jamaica’s north coast.
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Fairwinds Jamaica
4 bed / 4 bath villa in Montego Bay from $565 to $1,336 USD per night
Fairwinds is a beautiful four-bedroom private home with a magnificent sea view.
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