Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$1,500 - $2,395 /night
The Vacation Haven
4 Bedroom Villa, 5 Bathrooms, Sleeps 12
The Vacation Haven is a magnificent luxury villa located in the beautiful hills of the historic landmark Rose Hall, Montego Bay, Jamaica.
It is in a private gated community, adjacent to the beautiful Rose Hall Golf C... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,500 - $2,600 /night
Rocksteady Villa
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
Rocksteady Villa is a four-bedroom villa that features a 180-degree view of the ocean. You'll need to do nothing but relax as this villa offers chef service, a butler, housekeeping, and a groundsman. Inside you'll find t... more
Additional Fees: Damage Waiver $299.00 flat
$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
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: 20%
Taxes: 20%
$1,466 - $3,726 /night
Wheel House
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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 - $4,800 /night
Seaspray
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
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: 20%
Taxes: 20%
$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
True to its name, Tranquillity is a place for relaxing into the calm ambiance of an exquisite home on a waterfront site while being gently pampered by a competent staff.
The well-appointed rooms of Tranquility stretch... 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 - $2,981 /night
Avalon
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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 - $3,402 /night
Eureka
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$1,214 - $3,057 /night
Retreat Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$1,199 - $1,999 /night
Palm Villa
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Live the luxe life with a private swimming pool and covered outdoor living space at our Palm Villa.
This two-story oceanfront villa features five bedrooms with king beds, en-suite bathrooms, private verandas, a fully... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%
$1,199 - $1,999 /night
Cottonwood Villa
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Treat the whole family to our five-bedroom Cottonwood Villa, where a private swimming pool and covered outdoor living space overlook the ocean.
This exquisitely furnished villa features five bedrooms with king beds, ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%
$1,199 - $1,999 /night
Almond Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Plan a couple's vacation! The two-story oceanfront Almond Villa features four bedrooms with king-size beds and a private veranda.
Highlights include a living room, dining area, billiard room, and outdoor covered livi... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%
$1,199 - $1,999 /night
Naseberry Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Spread out in our two-floor, three-bedroom, three-bathroom Naseberry Villa.
Featuring a fully equipped kitchen, living room, dining area, bar, and powder room, as well as private verandas off of each bedroom, it’s ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%
$1,150 - $3,037 /night
Almond Hill
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Almond Hill is a lovely private home located on a former 500-acre coconut plantation just 22 minutes west of Montego Bay and a five-minute drive from Round Hill, where guests enjoy complimentary resort membership. A stun... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,142 - $2,500 /night
Spanish Cove
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Spanish Cove is the epitome of a Caribbean beach house tucked in the center of the small, busy town of Runaway Bay. Built in classic Jamaican style, with a wide veranda and beautiful decorative fan lights throughout, Spa... 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
$1,071 - $3,960 /night
Sunrise
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,050 - $3,949 /night
Noble House
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
This accommodation includes complimentary access to the Ocean Cliff Hotel in Negril, an 80-minute drive from the villa. You can enjoy their ocean-fed pool and sandy beach. Additional services such as meals from ... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,000 /night
Little Waters Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Little Waters on the Cliff is an exclusive private villa nestled on the cliffside at the westernmost point in Jamaica allowing guests to have an uninterrupted view of the setting sun. The house is architecturally designe... more
Additional Fees: Damage Waiver $299.00 flat
$1,000 - $1,500 /night
Villa Deluxe Paradise
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located in the cool hills of Discovery Bay, Jamaica, Villa Deluxe Paradise Vacation Home is a tranquil retreat blessed with world-class views across the Caribbean Sea. Once designed as a dream home, this exceptional vill... more
Additional Fees: Damage Waiver $299.00 flat