Caribbean Villa Rentals


Am

Amanoka on the Beach

Jamaica, Discovery Bay

from $2857 /night
up to 14 guests

Amanoka on the Beach

7 bedroom 8 bath Jamaica villa in Discovery Bay

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 turquoise water, and waterfront gazebo with suspended canvas swings.

Nl Copy

Bambu

Jamaica, Montego Bay

from $1357 /night
up to 14 guests

Bambu

7 bedroom 7 bath Jamaica villa in Montego Bay

Nine miles west of Montego Bay is a large private site overlooking perhaps the most glorious view of sea and sky on Jamaica’s renowned north coast. Elegantly perched on eight and a half acres atop this hill is Bambu, a grand six-bedroom private villa distinguished by its classic architecture and appreciated by discerning vacationers.

Cielo Nl Lr

Cielo at the Tryall Club

Jamaica, Montego Bay

from $1786 /night
up to 10 guests

Cielo at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

Cielo means "sky" and "heaven" and the name tells a lot about living in this wonderful villa on a hill. Add the all-day panorama of blue Caribbean Sea at every glance and "heaven" gets even better!

Dji

Haystack at the Tryall Club

Jamaica, Montego Bay

from $4000 /night
up to 20 guests

Haystack at the Tryall Club

10 bedroom 10 bath Jamaica villa in Montego Bay

Its remarkable architecture defines spacious bedroom suites, a long furnished verandah, a striking inside dining room and large family play room ~ all enhanced by overviews of the long private pool and acres of landscaped lawns and breathtaking views of the deep blue Caribbean Sea.

Rose Cottage Nl

Hyde Park at the Tryall Club

Jamaica, Montego Bay

from $1950 /night
up to 14 guests

Hyde Park at the Tryall Club

6 bedroom 8 bath Jamaica villa in Montego Bay

Hyde Park is a large and lavish home with glorious views of the lush Jamaican mountains and the deep blue Caribbean Sea. Its design is a stylish blend of Jamaican, Asian, and European elements with an emphasis on extraordinary comfort.

Makana

Makana on the Beach

Jamaica, Discovery Bay

from $3286 /night
up to 14 guests

Makana on the Beach

7 bedroom 7 bath Jamaica villa in Discovery Bay

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 private tennis court and swimming pool on a sugary white sand beach bordering translucent swimming and kayaking water.

Malatai NL +copy

Malatai on the Beach

Jamaica, Ocho Rios

from $5000 /night
up to 16 guests

Malatai on the Beach

8 bedroom 8.5 bath Jamaica villa in Ocho Rios

MALATAI has just undergone a Fabulous renovation, with 8 newly renovated bedrooms and bathrooms, a beachfront, and a top-rated chef, directly on the translucent waters of Mammee Bay, near Ocho Rios. While privately located, Malatai is only minutes from Dolphin Cove, famous Dunn‘s River Falls, and lively Ocho Rios with its wide selection of duty-free shopping, excursions, and music.

Viviana Nl

Sea Glass at Tryall Club

Jamaica, Montego Bay

from $1500 /night
up to 12 guests

Sea Glass at Tryall Club

6 bedroom 8 bath Jamaica villa in Montego Bay

Formerly named Annabella, Sea Glass sits on a remarkable six private acres on a plum site at the prestigious Tryall Club. Uniquely private, the feeling is being in a world of your own, wonderfully quiet and tranquil while just minutes away by complimentary golf cart are the amenities that have defined the Tryall Club as one of the finest private clubs in the world.

Bali Hai

Bali Hai at the Tryall Club

Jamaica, Montego Bay

from $1786 /night
up to 10 guests

Bali Hai at the Tryall Club

5 bedroom 6 bath Jamaica villa in Montego Bay

On seven acres overlooking the Tryall golf course and the Caribbean Sea, Bali Hai is among the most beautiful and spacious private homes at the Tryall Club. The unique architecture has situated all bedrooms for maximum privacy.

Following Seas Mix Nl

Following Seas at the Tryall Club

Jamaica, Montego Bay

from $2286 /night
up to 12 guests

Following Seas at the Tryall Club

6 bedroom 7 bath Jamaica villa in Montego Bay

Following Seas is a marvelous private villa with the top rating of Premier. It is tastefully renovated with thoughtful comforts, amenities and stylish bathrooms throughout.

Fortlands Point Nl

Fortlands Point on the Beach

Jamaica, Discovery Bay

from $3143 /night
up to 18 guests

Fortlands Point on the Beach

9 bedroom 9 bath Jamaica villa in Discovery Bay

On a stunning promontory, once the site of an old stone fort, sits a remarkable home named Fortlands Point. From its breathtaking location on the tip of the peninsula, the commanding view encompasses the turquoise water of Discovery Bay on one side and the deep blue Caribbean Sea on the other.

Infinity Nl

Infinity at the Tryall Club

Jamaica, Montego Bay

from $2530 /night
up to 12 guests

Infinity at the Tryall Club

6 bedroom 5.5 bath Jamaica villa in Montego Bay

A Premier villa at the renowned Tryall Club, Infinity is a halcyon haven overlooking the Caribbean Sea. Its rooms are large and tastefully furnished -- some traditional, some eclectic -- with a designer’s eye to comfort throughout. Named for its seemingly endless private pool, Infinity is a vacationer’s paradise for golf and tennis enthusiasts, spa weeks, family reunions or merely relaxing into the good life for a week or more.

Canoe Cove Nl

Canoe Cove on the Beach

Jamaica, Ocho Rios

from $4600 /night
up to 14 guests

Canoe Cove on the Beach

7 bedroom 8 bath Jamaica villa in Ocho Rios

In the 1950’s, Kingston attorney Clinton Hart happened onto this remarkable 3-acre waterfront location, bought it and built a simple beach cottage for his family. Through four generations, Canoe Cove has been a beloved family home, virtually unembellished. In 2015, Hart’s grandson replaced the worn cottage with a new sort of architecture, straightforward, uncomplicated and loaded with thoughtful comforts and essentials to redefine luxury in a beachy, barefoot lifestyle.

Noble House on the Beach

Jamaica, Montego Bay

from $1050 /night
up to 8 guests

Noble House on the Beach

4 bedroom 6 bath Jamaica villa in Montego Bay

A paradigm of elegance and style, Noble House on the Beach is an architectural gem, unique in the Caribbean.

Point+of+view+ +

Point of View at the Tryall Club

Jamaica, Montego Bay

from $2877 /night
up to 10 guests

Point of View at the Tryall Club

5 bedroom 5 bath Jamaica villa in Montego Bay

Located on the highest point at the renowned Tryall Club, Point of View sits on one of the most spectacular sites in the Caribbean … indeed, in the world. From its unique vantage point, a sweeping panorama stretches down the mountain and across the 18-hole championship golf course to the deep blue Caribbean and distant horizon. Breathtaking at every turn.

Ind

Villa Indigo

Jamaica, Montego Bay

from $2500 /night
up to 20 guests

Villa Indigo

10 bedroom 10 bath Jamaica villa in Montego Bay

Villa Indigo at HALF MOON is one of the undisputed finest private homes in this collection.

Aerial 2

Flower Hill

Jamaica, Montego Bay

from $2429 /night
up to 12 guests

Flower Hill

6 bedroom 12 bath Jamaica villa in Montego Bay

Flower Hill is one of the most luxurious villas in Montego Bay's, Spring Farm neighborhood. This Premier 19,000-sq-ft villa sits on 4 beautifully landscaped acres overlooking the Half Moon Beach Resort and Golf Club.

Silent Waters 9 Pool Sundeck Mobay Daytime

Silent Waters

Jamaica, Montego Bay

from $2853 /night
up to 16 guests

Silent Waters

8 bedroom 6 bath Jamaica villa in Montego Bay

Silent Waters is one of the most glamorous private homes in the Caribbean. It is distinguished by world-class architecture and design, breathtaking location, and exquisite accommodations and service.

Untitled

Rio Chico on the Beach

Jamaica, Ocho Rios

from $10413 /night
up to 24 guests

Rio Chico on the Beach

12 bedroom 12 bath Jamaica villa in Ocho Rios

Magnificent 14-acre oceanfront estate. Here is the rich character of The Riviera married to the superb service of Colonial Jamaica ... on a magnificent seascape just west of Ocho Rios on Jamaica's renowned north coast. Rio Chico's guest list includes diplomats, industrialists and celebrities from around the world.

Ani Villas Anguilla Cg 1 Long

Àni Anguilla Full Estate

Anguilla, Little Bay

from $16600 /night
up to 20 guests

Àni Anguilla Full Estate

10 bedroom 10.5 bath Anguilla villa in Little Bay

A clifftop eyrie perched above Little Bay on Anguilla's northern shoreline, Àni offers an entire, private resort on this jewel of a Caribbean Island, designed exclusively for a single group of guests.

Janmk 0 E 4

Àni Dominican Republic

Dominican Republic, Puerto Plata

from $16600 /night
up to 28 guests

Àni Dominican Republic

14 bedroom 14 bath Dominican Republic villa in Puerto Plata

Claiming its own private peninsula on the Dominican Republic’s north coast, Àni offers an all-inclusive, 4.2-acre (1.70-hectare) private resort exclusively designed for a single group of guests.

Find Caribbean Villas


Travel Dates
Travel Dates


Villa Size
Villa Size

Default minimum and maximum values represent the current range of villas in Caribbean.

Price Range
Price Range (per night)

Prices represent the starting per-night rate for matched villas. Default minimum and maximum prices represent the current range of villas in Caribbean.

Amenities
Amenities
Collections
Collections
Destinations
Destinations

If none are checked then all destinations are included.

Villa Destinations


Find Caribbean Villas