Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$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%
$1,050 - $3,949 /night
Noble House
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Noble House is a unique architectural gem by the sea. Its design is a series of airy pavilions with peaked roofs, its living spaces separated by water gardens and bridges. Indoor spaces flow into the outdoors with Orien... 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
$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 - $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 separate 3three-bedroom cottage. The villa is located on a private white sand beach on exclusive Fortlands Road in Discovery Bay.
The two-sto... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 5%
Taxes: 5%
$1,000 - $3,215 /night
Great River House
5 Bedroom Villa, 6 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
$1,000 - $1,571 /night
Blue Heaven Villa
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$994 - $2,467 /night
No Problem
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$985 - $2,142 /night
Sleepy Shallows
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Sleepy Shallows sits on a grassy lawn that stretches down to the white sandy beach and shallow waters of Bengal Bay. The villa embraces outdoor living with many places to sit and relax, read a book, or enjoy with friends... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$960 - $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%
$958 - $2,542 /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, a wide veranda, and beautiful decorative fan lights throughout, Spanish ... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$900 - $1,600 /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, equipped with modern conveniences such as satellite TV, VCR... more
Additional Fees: Damage Waiver $299.00 flat
$850 - $8,500 /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
$840 - $3,857 /night
Coach House at Good Hope
9 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%
$795 - $1,065 /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
$795 - $2,428 /night
Bluebird
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$794 /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 a bathroom en suite. Driftwood is a villa rental that may also ... more
Additional Fees: Damage Waiver $299.00 flat
$793 - $2,223 /night
Windsong Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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
$760 - $2,000 /night
Bee Happy
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$751 - $2,319 /night
Little Palm
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$743 - $1,980 /night
Poinciana
2 Bedroom Villa, 2 Bathrooms, Sleeps 4
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$742 - $1,458 /night
Jus Paradise
3 Bedroom Villa, 7 Bathrooms, Sleeps 6
Jus' Paradise is a charming private villa located in a gated residential area of upscale homes in the lush hills of Rose Hall.
Living areas are designed for relaxed Caribbean barefoot comfort, not fussy or formal. Fr... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$714 - $2,000 /night
Legacy Villa
2 Bedroom Villa, 2 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$689 /night
Seagrape Villa
1 Bedroom Villa, 1 Bathrooms, Sleeps 2
Dine in the fragrant tranquillity of your private walled garden in our one-bedroom, one-bathroom Seagrape Villa. This spacious retreat has a living room, full kitchen, a master bedroom with a king bed and a shared Jacuzz... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%
$642 - $1,715 /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: 17.5%
Taxes: 17.5%
$571 - $929 /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 - $917 /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 - $1,000 /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