Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$1,242 - $1,927 /night
Seven Seas
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The morning sun has turned the sea and the dew on the palm trees to silver. The non-stop trade winds waft through the rooms of the villa, and the aroma of fresh-baked bread works its way from the kitchen to the bedroom w... 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: 20%
Taxes: 20%
$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
$1,024 - $2,763 /night
No Problem
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$1,000 - $3,187 /night
Coach House at Good Hope
7 Bedroom Villa, 8 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: 20%
Taxes: 20%
$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%
$899 - $1,999 /night
Seagrape Villa
1 Bedroom Villa, 1 Bathrooms, Sleeps 2
Dine in the fragrant tranquility of your private walled garden in our one-bedroom, one-bathroom Seagrape Villa. This spacious retreat has a living room, a full kitchen, a primary bedroom with a king-size bed, and a share... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%
$850 - $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
$850 - $1,714 /night
Destiny on the Sea
4 Bedroom Villa, 3 Bathrooms, Sleeps 8
Destiny on the Sea, located in the gated beach community of Drax Hall Marina Villas, only 10 minutes from Ocho Rios, is a beautiful four-bedroom, three-bath villa, perfect for families or adults. This beautiful villa ope... more
Additional Fees: Damage Waiver $299.00 flat
$819 - $2,719 /night
Bluebird
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
Inquire for Rates
Villa Turrasann
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
Villa Turrasann is an enchanting beachfront villa located in Runaway Bay, Jamaica, 70 kilometers east and approximately a 60-minute drive from Montego Bay airport. Spanning an impressive 4,000 square feet, our property w... more
Additional Fees: Damage Waiver $299.00 flat, Cleaning Fee $15.00 flat
$793 - $2,360 /night
Windsong Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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, Service Fee $50.00 flat
$790 - $999 /night
Moonshine
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
A beautiful four-bedroom villa which opens out onto a lovely wooden deck with an infinity pool overlooking panoramic views of the Caribbean Sea.
One of Jamaica's most beautiful beaches, Silver Sands Beach is only a fe... more
Additional Fees: Damage Waiver $299.00 flat
$774 - $2,598 /night
Little Palm
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$765 - $2,218 /night
Poinciana
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$760 - $2,200 /night
Bee Happy
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$750 - $1,113 /night
Kotch
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
A unique sunset graces each evening sky. Morning swims. Feeling alive and energized, calm and relaxed all at the same time. The South Coast spirit draws you into a new sense of harmony and escape. Kotch’s expansive sea... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 25%
Taxes: 25%
$703 - $2,160 /night
Legacy Villa
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$650 - $795 /night
Driftwood Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
Driftwood is a stunning modern vacation villa with a private plunge pool in its bright and airy courtyard.
There are 3 spacious luxurious bedrooms, each with an en-suite. Driftwood is a villa rental that may also be ... more
Additional Fees: Damage Waiver $299.00 flat
$642 - $1,714 /night
Sea Haven
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Located on a private waterfront acre, Sea Haven is a traditional West Indian cottage dressed in charming periwinkle blue. It sits directly on the edge of beautiful Discovery Bay.
The living room is bright and airy wi... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$621 - $1,573 /night
Moments
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$571 - $1,000 /night
Terra Nova
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Terra Nova is a beautiful waterfront villa located in exclusive Mammee Bay. When you enter the villa you are immediately struck by the wonderful, spacious living/dining area with Italian marble floor and a 27-foot conica... more
Additional Fees: Damage Waiver $299.00 flat
$518 - $973 /night
Linga Awhile
3 Bedroom Villa, 4 Bathrooms, Sleeps 6
This three-bedroom casual cottage shares a delightful waterfront site with its neighbouring Villa, on the clear waters of Discovery Bay. Linga-Awile sits on a lovely, long, large lawn. Beyond the lawn and swimming pool i... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$500 - $1,062 /night
Summertime
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Summertime at Silver Sands has a wonderful beach vibe; it benefits from cool sea breezes and is a relaxed and unfussy villa located on the renowned Silver Sands Beach Club, a collection of privately owned villas all over... more
Additional Fees: Service Fee $50.00 flat, Damage Waiver $299.00 flat