Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$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
$1,471 - $4,800 /night
Seaspray
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,428 - $4,713 /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
$1,386 - $4,098 /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%
$1,365 - $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%
$1,360 - $2,981 /night
Avalon
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,357 - $3,946 /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
$1,328 - $3,402 /night
Eureka
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,299 - $3,057 /night
Retreat Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,242 - $1,927 /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
$1,240 - $2,370 /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
$1,228 - $4,195 /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
$1,210 - $3,226 /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
$1,207 - $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 - $3,200 /night
Sea Grapes
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Sea Grapes is a charming and well-appointed three-bedroom beach villa with a separate three-bedroom cottage. The villa is located on a private white sand beach on exclusive Fortlands Road in Discovery Bay.
The two-st... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 5%
Taxes: 5%
$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%
$1,179 - $3,960 /night
Sunrise
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,142 - $2,656 /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
$1,029 /night
Mai Tai Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
A beautiful 4 bedroom private, beachfront villa with amazing views, cool sea breeze and the relaxing sound of the waves touching the sand.
Mai Tai is one of the handful of villas in Silver Sands that provides full-tim... more
Additional Fees: Damage Waiver $299.00 flat
$1,024 - $2,763 /night
No Problem
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 17.5%
Taxes: 17.5%
$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
$1,000 - $3,187 /night
Coach House at Good Hope
7 Bedroom Villa, 10 Bathrooms, Sleeps 14
The Coach House at Good Hope is a fantastic informal gathering place for families, retreats, and friends - with space for togetherness, space for discovering nature, and space for alone time. Like traveling through a tim... more
Additional Fees: Service Fee $50.00 flat, Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$1,000 - $2,857 /night
Fairwinds
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,000 - $1,669 /night
Blue Heaven Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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, Service Fee $50.00 flat
$985 - $2,275 /night
Sleepy Shallows
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Sleepy Shallows is a lovely beachfront family-friendly property with newly updated interiors, located in the gated community of Bengal Bay in Rio Bueno, just 8 minutes from Discovery Bay and 50 minutes from Montego Bay.
... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$930 - $1,650 /night
Wag Water
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Wag Water is a charming three-bedroom villa overlooking the sea and forming part of the historic Prospect Estate.
The combination of a spacious living room along with an extensive covered veranda, with ample space fo... more
Additional Fees: Damage Waiver $299.00 flat
$899 - $1,999 /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-size bed, and two bathrooms. The ground floor bedroom and bathroom are wheelchair accessible for your c... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%