Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$1,571 - $5,000 /night
Windrush
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
Inquire for Rates
San Michele
6 Bedroom Villa, 6 Bathrooms, Sleeps 13
The largest of the Bluefield Bay villas, San Michele sits directly on the Caribbean Sea with 360-degree vistas of the mountains and sea. San Michele has a private island reached by footbridge where guests can spend count... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,543 - $3,400 /night
Jamaican Me Happy
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
Inquire for Rates
The Hermitage
4 Bedroom Villa, 3 Bathrooms, Sleeps 9
The Hermitage is designed with authentic Jamaican materials such as stone, marble, mahogany, and cedar to mirror features of authentic and traditional Jamaican homes. The villa features superb craftsmanship in mahogany a... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,500 - $3,143 /night
Abacus Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
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
$1,500 - $2,395 /night
The Vacation Haven
4 Bedroom Villa, 5 Bathrooms, Sleeps 12
The villa features a contemporary design with great attention to detail. The open-plan, spacious living areas are stylishly furnished and has an energetic Jamaican vibe.
One bedroom on the villa’s main level and th... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,500 - $2,700 /night
Frangipani
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Frangipani is the newest of luxury villas on the historic Prospect Estate. The spacious living room is equipped with a satellite TV, VCR, telephone, and stereo system. The central veranda leads out to a large pool with a... more
Additional Fees: Damage Waiver $299.00 flat
Inquire for Rates
Mullion Cove
6 Bedroom Villa, 5 Bathrooms, Sleeps 12
Perched thirty feet above the sea with commanding views, Mullion Cove is the original prototype for Bluefields Bay Villas. The villa features a cool veranda, tropical flower garden, outdoor tub off the primary bathroom, ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,466 - $3,549 /night
Wheel House
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,429 - $4,286 /night
Seaspray
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,372 /night
Villa Turrasann
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Villa Turrasann offers solitude, perfect for a family vacation, a romantic getaway or just as a home away from home. With 4,000sq feet, Villa Turrasann was made to be enjoyed, making it the perfect location for a holiday... more
Additional Fees: Damage Waiver $299.00 flat, Cleaning Fee $15.00 flat
$1,365 - $1,774 /night
Peeniwalli
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Pure and uniform, Peeniwalli’s white and neutral-toned appearance balances against a spellbinding backdrop of blue sky, rolling sea and lush vegetation. The colors come from living. It’s in the furniture and people, ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 25%
Taxes: 25%
$1,357 - $4,571 /night
Vista del Mar
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,357 - $3,715 /night
Allamanda
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
A special amenity available to guests in this villa is its complimentary membership with The Tryall Club. This membership enhances your stay with exclusive access to The Tryall Club's prestigious amenities and se... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,357 - $4,215 /night
Endless Summer
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
Endless Summer is a turreted mansion with views of the Caribbean Sea. From the porte-cochere, bevelled glass doors open to a dramatic 80-foot columned space. A sweeping white stone staircase curves gracefully from the fo... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,322 - $3,857 /night
Tranquility on the Beach
7 Bedroom Villa, 6 Bathrooms, Sleeps 14
The well-appointed rooms of Tranquility stretch over 6 300 square feet of rich marble floors. Artful landscaping ensures year-round flowers in bloom which in turn ensure regular visits from hummingbirds and parrots. The ... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
Taxes: 10%
Taxes: 10%
$1,286 - $5,571 /night
Love and Livity
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,271 - $2,786 /night
Avalon
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,265 - $3,240 /night
Eureka
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,242 - $1,815 /night
Seven Seas
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Designated a protected coconut plantation, the three acre grounds are dotted with 200 healthy coconut palms. Beds are piled high with plump pillows and duvets. Euro-chic bathrooms are immaculate. The outdoor Jacuzzi is b... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,239 /night
Mango Villa
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Our two-story Mango Villa has a living room, kitchenette and dining area, as well as two bedrooms, each with a king bed, and two bathrooms. Our ground-floor bedroom and bathroom are wheelchair accessible for your conveni... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%
$1,214 - $2,857 /night
Retreat Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,207 - $1,569 /night
Steppa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
A simple tropical modern design on a dramatic beachfront landscape, Steppa offers mountain to sea views at every turn. Sculpted white staircases and rounded curved walls allow cool ocean breezes to course through the vil... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 25%
Taxes: 25%
$1,200 - $2,300 /night
Somewhere
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Somewhere Villa is nestled in Prospect Estate's lush tropical garden overlooking the crystal clear waters of the Caribbean sea.
This spacious four bedroom, four bath villa is equipped with modern conveniences such as... more
Additional Fees: Damage Waiver $299.00 flat
$1,150 - $3,037 /night
Almond Hill
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
A stunning renovation has created the all-new design of picture-perfect bedrooms and modern en-suite bathrooms. Notable are two outdoor showers, one off the master bedroom, and another by the pool.
Tall library shelv... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,092 - $2,358 /night
Serenity by the Sea
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Serenity is one of the most beloved and often revisited villas on Jamaica's beautiful north coast. Its prize location is a waterfront acre 8 miles west of Montego Bay. Grounds include a shared tennis court, basketball ho... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
Inquire for Rates
Providence House
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Providence House sits on the calmest slice of the Bay. At sea level, 46-steps away, is a cave with hammock, lounge chairs and dining area. The main house features three nearly identical master bedroom suites, a living ro... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
Inquire for Rates
Cottonwood Cottage
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The most nature-integrated villa, Cottonwood Cottage has two-bedroom suites on four beachfront acres surrounded by dense tropical foliage. The Treehouse, located below Cottonwood, is a bar, living, and dining space overl... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$1,071 - $3,600 /night
Sunrise
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
Inquire for Rates
Milestone Cottage
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
Milestone Cottage has always been the honeymoon favorite, although also popular for small families with its two bedrooms. Built many years earlier, it was purchased in 1986 and extensively remodeled and personalized. Thi... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%