Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$2,749 /night
Cottonwood Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Guests of Cottonwood receive a complimentary membership to Swept Away Sports centre. Membership benefits include access to the fitness centre, 25-metre lap pool, tennis courts, squash courts, raquetball courts an... more
Taxes: 20%
$2,708 - $5,610 /night
Infinity
6 Bedroom Villa, 5 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,700 - $5,714 /night
Selah Villa
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Selah Villa is situated on the edge of a nature reserve, hundreds of years old, which is home to doves and local bird life. Jeremy Millingen's (architect and designer) international experience was challenged to achieve t... more
Additional Fees: Pre-stock Fee $500.00 flat, Damage Waiver $299.00 flat, Grocery Deposit $1500.00 flat
$2,668 - $6,042 /night
Twin Palms
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $7000.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,571 /night
Mais Oui Villa
8 Bedroom Villa, 11 Bathrooms, Sleeps 16
Why settle for an average vacation rental home when you can book something truly spectacular? When you book a stay at our luxury villa in Discovery Bay Jamaica, you get the amenities of a 5-star resort, without having to... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$2,571 - $5,714 /night
Trinity
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,571 - $5,663 /night
Phoenix
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,550 - $7,143 /night
Bella Vista Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,464 - $9,280 /night
Amana
10 Bedroom Villa, 10 Bathrooms, Sleeps 20
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,450 - $5,000 /night
Flower Hill
6 Bedroom Villa, 10 Bathrooms, Sleeps 12
This accommodation includes a complimentary Half Moon Resort membership which grants access to the Half Moon Golf Club. Benefits include unlimited green fees and use of practice facilities, 25% discount on option... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,377 - $5,607 /night
Celestial Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,362 - $6,429 /night
Ambiance Sea Salt
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,357 - $5,714 /night
Sunset
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,357 - $5,143 /night
Keela Wee
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Located on a private coral cove, this pretty yellow stone villa overlooks one of Jamaica's loveliest bodies of water, Discovery Bay. On its own private coral cove, this property can be rented alone, or in combination wit... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,286 - $5,429 /night
Breakaway Villa
7 Bedroom Villa, 7 Bathrooms, Sleeps 16
Construction is taking place on the pickleball and basketball court and may create some noise issues. Contact a Rental Escapes villa specialist for more information about how this may impact your stay.
... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$2,286 - $6,006 /night
Little Hill
5 Bedroom Villa, 4 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $5000.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,286 - $5,000 /night
Tradewinds on the Sea
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,286 - $7,433 /night
Following Seas
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $3000.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,286 - $4,000 /night
Golden Clouds
15 Bedroom Estate, 17 Bathrooms, Sleeps 30
Golden Clouds Country Estate is a spectacular waterfront villa located in the picturesque village of Oracabessa.
Fifteen minutes from Ocho Rios, on Jamaica's fabled North Coast and neighboring Ian Fleming’s "Golden... more
Additional Fees: Damage Waiver $299.00 flat
$2,279 - $5,240 /night
Someday Soon
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,251 - $6,000 /night
Hyde Park
6 Bedroom Villa, 9 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,245 - $3,350 /night
Timbuktu By The Sea
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
Timbuktu is a modern, contemporary villa with the most beautiful seafront. The entrance is through handsomely carved doors that lead into the main living area. A covered verandah and dining area lead out to the pool with... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,209 - $5,146 /night
Bougainvillea House
5 Bedroom Villa, 5 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,199 /night
Almond Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Ideal for couples travelling together, the two-story oceanfront Almond Villa features four king bed bedrooms, each with a private veranda. Highlights include a living room, dining area, billiard room, and outdoor covered... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%
$2,160 - $4,500 /night
Olive Branch Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 12
Just three minutes from the beach and nestled in the hills of Oracabessa, Olive Branch Villa sits on beautifully landscaped grounds boasting a panoramic view of the Caribbean Sea’s coastline, with cool hills hugging th... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$2,132 - $7,566 /night
Karma Bay
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 17.5%
Taxes: 17.5%
$2,100 - $5,280 /night
A Summer Place
7 Bedroom Villa, 9 Bathrooms, Sleeps 14
Nestled on its own sandy beach by the blue waters of Discovery Bay, A Summer Place is a spacious and playful family home. The design is of typical Caribbean gingerbread style with hand carved fretwork trimming the length... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,090 - $4,650 /night
Fairway Manor
7 Bedroom Villa, 9 Bathrooms, Sleeps 14
This accommodation includes a complimentary Half Moon Resort membership which grants access to the Half Moon Golf Club. Benefits include unlimited green fees and use of practice facilities, 25% discount on option... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,090 - $4,563 /night
Villa Paradiso
8 Bedroom Villa, 8 Bathrooms, Sleeps 18
Welcome to Villa Paradiso, an exquisite villa in the prestigious Mammee Bay Estate in Ocho Rios. Renowned for its pristine white sand beaches and captivating attractions like Dunn’s River Falls, Dolphin Cove, and Mysti... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$2,071 - $4,271 /night
Villa Christina
5 Bedroom Villa, 7 Bathrooms, Sleeps 11
Villa Christina's Tuscan estate offers five luxury bedroom suites featuring stunning views of both the Caribbean Sea and the mountains. Generous entertainment areas include a billiards room complete with a wet bar and ei... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
Taxes: 10%
Taxes: 10%