Jamaica Vacation Rentals
Luxury Villa Rentals in Jamaica for 2+ people
$11,038 - $26,046 /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
$5,572 - $9,285 /night
Happy Hour
7 Bedroom Villa, 8 Bathrooms, Sleeps 14
Happy Hour is truly an exquisite new home, decorated in contemporary muted tones throughout, comfort abounds. Located in the gated community of Fortlands Road in Discovery Bay, where villas have private sandy waterfronts... more
Additional Fees: Service Fee $50.00 flat, Damage Waiver $299.00 flat
$5,500 - $10,000 /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
$5,143 - $15,000 /night
Haystack
10 Bedroom Villa, 10 Bathrooms, Sleeps 20
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$5,000 - $8,500 /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
$4,600 - $7,050 /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
$4,000 - $7,429 /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 si... more
Additional Fees: Service Fee $50.00 flat, Damage Waiver $299.00 flat
$3,600 - $7,050 /night
Buttonwood Reef
8 Bedroom Villa, 9 Bathrooms, Sleeps 16
This incredible new villa faces the ocean front and center.
From the minute you enter the villa, through the dramatic Jequitiba wood ceiling entranceway and over-sized pivot door, your eye meets the Caribbean Sea. It ... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$3,500 - $5,500 /night
Reverie
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Reverie is a very private tropical oasis, 8,500 sq ft of 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, walls of d... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$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: 17.5%
Taxes: 17.5%
$3,429 - $8,571 /night
Oceana
6 Bedroom Villa, 6 Bathrooms, Sleeps 12
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$3,358 - $5,991 /night
Aqua Bay
4 Bedroom Villa, 4 Bathrooms, Sleeps 8
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$3,300 /night
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 from the world famous Half Moon Golf Course in Montego Bay.
An Exclusively Elegant Boutique Villa, ... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$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: 17.5%
Taxes: 17.5%
$3,285 - $5,715 /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
$3,253 - $10,714 /night
Stella by the Sea
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$3,142 - $7,715 /night
Sea Salt at Old Fort Bay
9 Bedroom Villa, 9 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. There is a top-notch staff that will look after your every wi... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
$3,142 - $5,715 /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%
$3,142 - $6,572 /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, Security Deposit $3000.00 flat
$3,071 - $5,714 /night
Pineapple House
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$3,035 - $6,929 /night
Aquamarina Villa
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
Aquamarina is a beautiful luxury villa perched on the top of the hill with complete sea frontage, the views are fabulous. Located on the east side of Ocho Rios, about ten minutes from the center of town. Aquamarina’s r... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
Taxes: 15%
Taxes: 15%
$3,000 - $6,143 /night
Villa Lido
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
This old family home has been re-born as a fabulous contemporary beach house. Situated right on the white sand, half-moon beach at Old Fort Bay. Beautifully designed and finished, incorporating family air looms and a chi... more
Additional Fees: Service Fee $50.00 flat, Damage Waiver $299.00 flat
$3,000 - $6,857 /night
Dragonfly
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$2,986 - $7,986 /night
Hummingbird House
7 Bedroom Villa, 7 Bathrooms, Sleeps 14
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$2,877 - $5,603 /night
Point of View
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$2,857 - $6,286 /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 alo... 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
Set atop one of the highest mountaintops overlooking Montego Bay and the Caribbean Sea, Silent Waters Villa offers a secluded retreat just 4.6 miles west of Montego Bay. This breathtaking 16.5-acre estate combines world-... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 10%
Taxes: 10%
$2,751 - $5,532 /night
Zion Hill
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
The Tryall Club requires all villa and condo guests to become members during their stay via a Temporary Membership Fee ($) (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: 17.5%
Taxes: 17.5%
$2,750 - $3,000 /night
Villa Indigo
5 Bedroom Villa, 6 Bathrooms, Sleeps 10
This accommodation includes a complimentary Half Moon Resort membership which grants access to the Half Moon Golf Club. Benefits include unlimited green fees and use of practice facilities, 25% discount on option... more
Additional Fees: Damage Waiver $299.00 flat, Service Fee $50.00 flat
Taxes: 10%
Taxes: 10%
$2,749 /night
Palm Villa
5 Bedroom Villa, 5 Bathrooms, Sleeps 10
A private swimming pool and covered outdoor living room are highlights of our Palm Villa. Featuring five bedrooms with king bed, en suite bathrooms and private veranda, this two-story oceanfront villa has a fully equippe... more
Additional Fees: Damage Waiver $299.00 flat
Taxes: 20%
Taxes: 20%