Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$11,589 - $29,497 /night
Rio Chico Private Estate
12 Bedroom Villa, 12 Bathrooms, Sleeps 24
Pass through the wrought iron gates and begin a magical journey down a quiet winding road, where a sprawling Great Lawn, at once wild and manicured, is rimmed by verdant gardens dotted with streams and waterfalls, ivy-co... more
Additional Fees: Security Deposit $10000.00 flat
$7,500 - $12,500 /night
Opulenz Villa
12 Bedroom Villa, 14 Bathrooms, Sleeps 24
A private tropical oasis near the shores of one of the best beaches on the north coast of Jamaica. It’s situated in the community of Drax Hall Estate, 15 minutes from Ocho Rios.
Immerse yourself in the art of leisur... more
Additional Fees: Damage Waiver $299.00 flat
Inquire for Rates
MilBrooks Resort Villa
10 Bedroom Villa, 11 Bathrooms, Sleeps 20
Surround yourself with the timeless elegance of Milbrooks Resort, Rose Hall, Jamaica. Located within walking distance of the world-famous Half Moon Golf Course in Montego Bay.
An Exclusively Elegant Boutique Villa, su... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$6,000 - $15,000 /night
Haystack
10 Bedroom Villa, 10 Bathrooms, Sleeps 20
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $3000.00 flat
Taxes: 20%
Taxes: 20%
$5,670 - $10,300 /night
Frankfort
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Frankfort has once again reaffirmed its position as one of the most desirable properties in Jamaica with the addition of a beautiful new swimming pool. Completed in 2019, the pool complements what is arguably the best pr... more
Additional Fees: Damage Waiver $299.00 flat
$5,572 - $9,865 /night
Happy Hour
7 Bedroom Villa, 8 Bathrooms, Sleeps 15
Happy Hour is truly an exquisite new home, decorated in contemporary muted tones throughout, and comfort abounds. Located in the gated community of Fortlands Road in Discovery Bay, where villas have private sandy waterfr... more
Additional Fees: Service Fee $50.00 flat, Damage Waiver $299.00 flat
$5,000 - $9,031 /night
Malatai
8 Bedroom Villa, 10 Bathrooms, Sleeps 16
Malatai is a fabulous contemporary home with modern updated bedrooms and noteworthy bathrooms nestled on a wide beachfront on the beautiful Old Fort Bay Beach. While privately located, Malatai is only minutes from Dolphi... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$4,857 - $8,650 /night
Sea Salt at Old Fort Bay
9 Bedroom Villa, 10 Bathrooms, Sleeps 18
Sea Salt is the perfect family or friend’s getaway, situated on two beautifully cared-for lawns that nudge the golden sand half-moon beach of Old Fort Bay! It is made up of a 5-bedroom main house on the beachfront with... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$4,600 - $7,490 /night
Canoe Cove
7 Bedroom Villa, 9 Bathrooms, Sleeps 14
Here is a dream come true for the three-generation family whose wish list of individual requirements includes copious space for togetherness; intimate space to take a nap, finish a novel or have a massage; sporting optio... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$4,250 - $7,362 /night
Aquamarina Villa
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Aquamarina boasts updated, contemporary interiors, with every room offering breathtaking views of the Caribbean. This stunning 6,000 sq. ft. villa overlooks crystal-clear waters and features a private sandy cove and one ... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
Taxes: 15%
Taxes: 15%
$4,000 - $7,893 /night
Promiseas
8 Bedroom Villa, 8 Bathrooms, Sleeps 16
Please note that the private spa is currently unavailable.:
Promiseas Villas are located on a fabulous private sandy cove, which are newly completed and exceptional in every way imaginable.
These s... more
Additional Fees: Service Fee $50.00 flat, Damage Waiver $299.00 flat
$3,600 - $7,490 /night
Buttonwood Reef
8 Bedroom Villa, 9 Bathrooms, Sleeps 16
This incredible contemporary villa faces the ocean front and center.
From the minute you enter the villa, through the dramatic Jequitiba wood ceiling entranceway and oversized pivot door, your eye meets the Caribbean ... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$3,578 - $11,786 /night
Stella by the Sea
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$3,531 - $9,600 /night
Oceana
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $6000.00 flat
Taxes: 20%
Taxes: 20%
$3,499 - $7,748 /night
Harmony Hill
7 Bedroom Villa, 8 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$3,459 - $6,710 /night
Aqua Bay
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $3000.00 flat
Taxes: 20%
Taxes: 20%
$3,286 - $9,000 /night
Sundance
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$3,285 - $7,285 /night
Fortlands Point
9 Bedroom Villa, 9 Bathrooms, Sleeps 18
On a stunning promontory, once the site of an old stone fort, sits a remarkable Premier home named Fortlands Point. From its breathtaking location on the tip of the peninsula, the commanding view encompasses the turquois... more
Additional Fees: Service Fee $50.00 flat, Damage Waiver $299.00 flat
$3,285 - $6,071 /night
Makana
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay. The site itself is remarkable: a spacious villa with a private tennis court and swimming pool on a sugary white... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$3,284 - $8,785 /night
Hummingbird House
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$3,225 - $6,246 /night
Pineapple House
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$3,143 - $7,857 /night
Dragonfly
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$3,142 - $6,071 /night
Amanoka
7 Bedroom Villa, 8 Bathrooms, Sleeps 14
Located on beautiful Discovery Bay, Amanoka is one of the most stunning villas in this collection. From the spacious verandah and pool, a barefoot stroll leads down a soft lawn to the 70’ white sand beach, clear turquo... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
Taxes: 5%
Taxes: 5%
$3,000 - $6,525 /night
Villa Lido
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Entering Villa Lido to the wide-open view of the bay and Caribbean Sea beyond is a sight for sore eyes. Cool, elegant, modern interiors invite you in. The view is maximized by the open walls of glass. Every element of th... more
Additional Fees: Service Fee $50.00 flat, Damage Waiver $299.00 flat
$2,963 - $6,275 /night
Point of View
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $3500.00 flat
Taxes: 20%
Taxes: 20%
$2,906 - $6,280 /night
Celestial Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,857 - $6,677 /night
Whispering Waters
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
Whispering Waters offers seven bedrooms and en-suite bathrooms. Overlooking one of Jamaica’s loveliest, crystal clear bodies of water, Discovery Bay. On its own private coral cove, this newest property can be rented al... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,853 - $7,845 /night
Silent Waters Villa
9 Bedroom Villa, 6 Bathrooms, Sleeps 20
This luxury villa resort is a superb location for a family reunion, corporate retreat, destination wedding, or just a group of friends seeking a most unique and luxurious holiday experience.
Nestled in the hills of Ja... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$2,828 - $6,405 /night
Twin Palms
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $7000.00 flat
Taxes: 20%
Taxes: 20%
$2,800 - $5,843 /night
Reverie
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Reverie is a very private tropical oasis, 8,500 sq ft villa on an acre of land, nestled in a serene bay community near the shores of one of the best beaches on the north coast.
Inside and outside living, the walls of ... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
Taxes: 10%
Taxes: 10%
$2,800 - $5,714 /night
Selah Villa
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
Selah is a lush four-bedroom villa located in Runaway Bay. It sits on the sea where the waves gently break on shallow reefs and roll in, providing their own music. The beach is one mile of white sand for sunbathing, stro... more
Additional Fees: Pre-stocking Fee $500.00 flat, Grocery Deposit $3500.00 flat, Damage Waiver $299.00 flat
$2,678 - $8,000 /night
Bella Vista Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,649 - $6,400 /night
Trinity
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,649 - $6,230 /night
Phoenix
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$2,571 - $5,714 /night
Breakaway Villa
7 Bedroom Villa, 7 Bathrooms, Sleeps 16
This beautiful seven-bedroom, beachfront villa is located in the Salem area, just east of Runaway Bay. The modern architecture and furnishings create the perfect getaway for your dream Jamaican paradise. The welcoming an... more
Additional Fees: Damage Deposit $2500.00 flat
Taxes: 10%
Taxes: 10%
$2,538 - $10,394 /night
Amana
10 Bedroom Villa, 10 Bathrooms, Sleeps 20
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$2,500 - $6,000 /night
Bougainvillea House
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,450 - $3,500 /night
Mais Oui Villa
8 Bedroom Villa, 11 Bathrooms, Sleeps 16
Why settle for an average vacation rental home when you can book something truly spectacular? When you book a stay at our luxury villa in Discovery Bay Jamaica, you get the amenities of a 5-star resort, without having to... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 25%
Taxes: 25%
$2,450 - $5,312 /night
Flower Hill
6 Bedroom Villa, 10 Bathrooms, Sleeps 12
Guests of Flower Hill receive complimentary access to the Rose Hall Club. Benefits include discounted green fees at Cinnamon Hill and White Witch Golf Courses. Cart and caddie fees are separate. Caddies are manda... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,433 - $7,200 /night
Ambiance Sea Salt
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,428 - $6,528 /night
Sunset
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,363 - $6,300 /night
Hyde Park
6 Bedroom Villa, 9 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,357 - $5,463 /night
Keela Wee
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Located on a private coral cove, this pretty yellow stone villa overlooks one of Jamaica's loveliest bodies of water, Discovery Bay. On its own private coral cove, this property can be rented alone, or in combination wit... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,354 - $8,325 /night
Following Seas
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $3000.00 flat
Taxes: 20%
Taxes: 20%
$2,352 - $5,610 /night
A Summer Place
7 Bedroom Villa, 9 Bathrooms, Sleeps 14
Nestled on its own sandy beach by the blue waters of Discovery Bay, A Summer Place is a spacious and playful family home. The design is of typical Caribbean gingerbread style with hand carved fretwork trimming the length... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,350 - $5,487 /night
Sea Glass
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,347 - $5,869 /night
Someday Soon
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,286 - $5,600 /night
Tradewinds on the Sea
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$2,286 - $4,000 /night
Golden Clouds
15 Bedroom Estate, 17 Bathrooms, Sleeps 30
Golden Clouds Country Estate is a spectacular waterfront villa located in the picturesque village of Oracabessa.
Fifteen minutes from Ocho Rios, on Jamaica's fabled North Coast and neighboring Ian Fleming’s "Golden... more
Additional Fees: Damage Waiver $299.00 flat
$2,252 - $8,474 /night
Karma Bay
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,245 - $3,532 /night
Timbuktu By The Sea
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Timbuktu is a modern, contemporary villa with the most beautiful seafront. The entrance is through handsomely carved doors that lead into the main living area. A covered verandah and dining area lead out to the pool with... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,214 - $5,084 /night
Hidden Bay by the Sea
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
The extraordinary location of this unique cliffside home is absolutely stunning. Planted firmly on a rock ledge high above the sea, the precipice may be daunting to some. While a low stone wall wraps most of the waterfro... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,160 - $3,500 /night
Olive Branch Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 12
Just three minutes from the beach and nestled in the hills of Oracabessa, Olive Branch Villa sits on beautifully landscaped grounds boasting a panoramic view of the Caribbean Sea’s coastline, with cool hills hugging th... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 15%
Taxes: 15%
$2,148 - $5,610 /night
Infinity
6 Bedroom Villa, 5 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,140 - $4,940 /night
Fairway Manor
7 Bedroom Villa, 9 Bathrooms, Sleeps 14
Guests of BougainVilla on Spring Farm receive complimentary access to the Rose Hall Club. Benefits include discounted green fees at Cinnamon Hill and White Witch Golf Courses. Cart and caddie fees are separate. C... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,100 - $6,900 /night
Sugar Hill
8 Bedroom Villa, 8 Bathrooms, Sleeps 16
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$2,100 - $6,129 /night
Bumper's Nest
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,098 - $5,770 /night
Hanover Windward
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$2,090 - $4,563 /night
Villa Paradiso
8 Bedroom Villa, 8 Bathrooms, Sleeps 18
Welcome to Villa Paradiso, an exquisite villa in the prestigious Mammee Bay Estate in Ocho Rios. Renowned for its pristine white sand beaches and captivating attractions like Dunn’s River Falls, Dolphin Cove, and Mysti... more
Additional Fees: Damage Waiver $299.00 flat
$2,071 - $4,537 /night
Villa Christina
5 Bedroom Villa, 7 Bathrooms, Sleeps 11
Set on the historic Rose Hall Estate, Villa Christina welcomes couples, families, and friends to Caribbean luxury in a remarkable 10,000 sq. ft., well-appointed Tuscan-style villa located in the Greens at Rose Hall - a p... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
Taxes: 10%
Taxes: 10%
$2,023 - $4,790 /night
Casuarina
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$2,000 - $3,642 /night
BougainVilla on Spring Farm
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Guests of BougainVilla on Spring Farm receive complimentary access to the Rose Hall Club. Benefits include discounted green fees at Cinnamon Hill and White Witch Golf Courses. Cart and caddie fees are separate. C... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,000 - $3,642 /night
Villa Rosa
5 Bedroom Villa, 7 Bathrooms, Sleeps 10
Guests of Villa Rosa receive complimentary access to the Rose Hall Club. Benefits include discounted green fees at Cinnamon Hill and White Witch Golf Courses. Cart and caddie fees are separate. Caddies are mandat... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$2,000 - $4,643 /night
Cielo
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $2500.00 flat
Taxes: 20%
Taxes: 20%
$1,986 - $4,400 /night
Ma Moura
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,964 - $5,175 /night
Sugar Bay
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
On its own sugary white sand beach lapped by the turquoise waters of Discovery Bay sits the exquisite home Sugar Bay. Interiors have just been refreshed throughout and are distinguished by elegant custom-designed furnitu... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,921 - $5,410 /night
Sweet Spot
6 Bedroom Villa, 7 Bathrooms, Sleeps 12
Located on a wide sandy beach, Sweet Spot is like a pretty jewel box next to the sea. Its remarkable location is the best of all worlds. A 6,000-square-foot private home with a huge lawn and beach.
Interiors at Sweet ... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$1,900 - $5,567 /night
Villa Lolita
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$1,865 - $6,727 /night
Little Hill
5 Bedroom Villa, 4 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (plus a 15% service charge). Children between the ages of 13 and 15 pay at a discounted r... more
Additional Fees: Security Deposit $5000.00 flat
Taxes: 20%
Taxes: 20%
$1,857 - $4,571 /night
Vista del Mar
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$1,854 - $7,903 /night
Hanover Grange
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$1,850 /night
Villa Mimosa
5 Bedroom Villa, 8 Bathrooms, Sleeps 10
The Mimosa: it’s a fragrant tropical plant, a favorite cocktail, and your welcome drink when you arrive at Villa Mimosa in Discovery Bay, Jamaica. Take your first refreshing sips in paradise as you explore this ultra-l... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 25%
Taxes: 25%
$1,839 - $3,358 /night
White Owl
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,800 - $3,450 /night
Sugar Magnolia
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,786 - $4,000 /night
Three Little Birds
4 Bedroom Villa, 5 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,770 - $4,851 /night
Round House
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,755 - $5,500 /night
Kai Kala
10 Bedroom Estate, 10 Bathrooms, Sleeps 22
Guests should be aware that part of the villa is perched near a large cliff that can be dangerous for small children and large groups. Please take this into consideration when making your booking.
... more
Additional Fees: Damage Deposit $2500.00 flat
$1,749 - $5,091 /night
Reef House
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,738 - $5,583 /night
Anticipation
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$1,654 - $5,263 /night
Jubilation
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$1,650 - $3,090 /night
Eight Rivers
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Eight Rivers is a delightful, architect-designed home that has been totally updated and renovated in the past few years. The villa is a spacious four-bedroom with 1-1/2 acres of manicured gardens on the Prospect Estate o... more
Additional Fees: Damage Waiver $299.00 flat
$1,643 - $2,214 /night
Wine Down
5 Bedroom Villa, 7 Bathrooms, Sleeps 12
This home does not have air-conditioning
A beautiful family home built in 2017 to include all of the luxurious amenities to make your vacation a memorable and relaxing one.
Located in the beautif... more
Additional Fees: Damage Waiver $299.00 flat
$1,643 - $3,571 /night
Jamaican Me Happy
3 Bedroom Villa, 3 Bathrooms, Sleeps 6
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$1,620 - $3,500 /night
Scotch on the Rocks
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
This oceanfront five-bedroom, five-bath villa is nestled in lush tropical, orchid-filled gardens overlooking the sea. The villa was originally built by a Scottish lord, the Earl of Mansfield, in the early 1950's.
Scot... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 5%
Taxes: 5%
$1,619 - $5,600 /night
Windrush
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$1,575 - $5,850 /night
Love and Livity
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$1,550 - $2,780 /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
$1,539 - $3,726 /night
Wheel House
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$1,529 - $3,766 /night
Yellowbird
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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%
$1,500 - $3,338 /night
Abacus Villa
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
Guests of Abacus Villa receive complimentary access to the Rose Hall Club. Benefits include discounted green fees at Cinnamon Hill and White Witch Golf Courses. Cart and caddie fees are separate. Caddies are mand... 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 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
$1,471 - $4,800 /night
Seaspray
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 20%
Taxes: 20%
$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, Tranquility 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: 20%
Taxes: 20%
$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: 20%
Taxes: 20%
$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: 20%
Taxes: 20%