Browse 195 Villas

From $1300.00 Per Night

Elsewhere , Coopers Hill, Sandy Lane Estate, St. James

Elsewhere is an exceptionally beautiful villa that sprawls on the Sandy Lane Estate on Barbados' famed Platinum Coast. Built as a "labour of love" twenty years ago, it has Mediterranean style architecture with stucco walls and terracotta tiled roof that encompass terraces, balconies, patios and courtyards. The villa extends over three wings affording plenty of privacy to guests. There is the Main House with four bedrooms, the Pool House with ...

Barbados, Golf Course, Coopers Hill, Sandy Lane Estate, St. James
8 Bedrooms , 8 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 16


View Villa Details
From $2200.00 Per Night

Elysium, Coral Cliff, St. Peter

Providing the perfect blend of contemporary design and alluring décor, Elysium is a luxury 6 bedroom private residence just minutes away from the beach. Blending Caribbean design with Balinese influences Elysium is a tranquil oasis situated in Coral Cliff, St. Peter; just beyond the Port Ferdinand marina. Its open plan living and dining areas, infinity pool and pool deck gazebos lend perfectly to large family gatherings, lazy afternoons or romantic ...

Barbados, Hillside,, Coral Cliff, St. Peter
6 Bedrooms , 6 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 12


View Villa Details
From $1285.71 Per Night

Endless Summer, Montego Bay

Endless Summer is a turreted mansion with views of the Caribbean Sea. From the porte-cochere, beveled glass doors open to a dramatic 80' columned space. A sweeping white stone staircase curves gracefully from the foyer to a balustraded gallery encircling and overlooking the sunken living room ... topped high above by the dome of this home's highest turret. From the gallery, as from all bedrooms, a wall of glass doors ...

Jamaica, Golf Course, Montego Bay
6 Bedrooms , 6 Bathrooms
Maximum Occupancy: 12


View Villa Details
From $2642.86 Per Night

Fabrizia , Gustavia

One of our more roomy villas! One of the most requested villas! One of the most beautiful ocean views on Gustavia! One of the most spacious villas of the island! “Fabrizia” is the largest villa of the private estate of “Le Domaine du Soleil Couchant” located on the heights of Gustavia. This villa has a stunning ocean view on the ocean, and the harbour of Gustavia. The very large swimming pool is ...

St. Barts, Hillside, Gustavia
8 Bedrooms , 8 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 18


View Villa Details
From $1420.00 Per Night

Fairway Manor, Montego Bay

Fairway Manor is a 5,600-square-foot 2-storyprivate home overlooking the famous Half Moon 18-hole Robert Trent Jones golf course and the sea. In the fall of 2008, the new owner upgraded the villa with new furniture, new bedding, tile, paint, powder room and televisions throughout … as well as a new inside staircase and enlargement of two of the downstairs bedrooms and bathrooms. Fairway Manor’s rooms open onto verandahs and balconies where the ...

Jamaica, Golf Course, Montego Bay
7 Bedrooms , 8 Bathrooms
Maximum Occupancy: 14


View Villa Details
From $1948.00 Per Night

Following Seas, Tryall Club, Montego Bay

Following Seas is one of Tryalls large Premier rated (the highest rating in the Tryall Club) villa set on 7 acres of manicured lawns and gardens. The villa is a one of a kind villa which truly offers the ultimate in comfort and distinctive decor. With a staff of 7 at your service, this villa will allow you the complete rest and relaxations, with every need looked after. Following Seas ...

Jamaica, Hillside, Tryall Club, Montego Bay
6 Bedrooms , 7 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 12


View Villa Details
From $2571.43 Per Night

Fortlands Point, Discovery Bay

On a stunning promontory, once the site of an old stone fort, sits a remarkable new 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. The views are simply magnificent. The clear buoyant water and adjacent reefs are a paradise for snorkelers and ...

Jamaica, Beachfront, Discovery Bay
7 Bedrooms , 7 Bathrooms
Maximum Occupancy: 14


View Villa Details
From $3188.00 Per Night

Fustic House, St. Lucy, Barbados

Fustic House is a privately owned 11-acre estate that dates back to 1740. The extensive property with mesmersing panoramic views of the Caribbean coastline is set on a ridge, where tradewinds provide welcome cooling breezes. The property was re-designed in the late 1970's by the English theatrical designer, Oliver Messel whose distinctive style was to create a series of indoor and outdoor living areas that flow seamlessly together. Fustic House ...

Barbados, Hillside/close to beach, St. Lucy, Barbados
7 Bedrooms , 7 Bathrooms
Maximum Occupancy: 14


View Villa Details
From $3400.00 Per Night

Gardenia, The Garden, St. James

Gardenia is ideally situated on the ‘platinum’ West Coast of Barbados, less than 10-minutes drive from the historic towns of Holetown and Speightstown. This luxurious beachfront villa is also strategically positioned within minutes of the exclusive golfing communities of Royal Westmoreland and Sandy Lane.Nestled amidst 3.3 acres of beautifully landscaped gardens, this stunning 6-bedroom beachfront villa is the perfect mix of luxury, comfort and privacy. Its elevated position on an ...

Barbados, Beachfront, The Garden, St. James
6 Bedrooms , 6 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 12


View Villa Details
From $0.00 Per Night

Ginger Lily, Upper Carlton, St James

Ginger Lily is a beautiful villa with spectacular views of the West Coast. This impressive home is built of coral stone and is immaculately furnished and just a ten minute drive from the beach.Within the villa you will find arched doorways, tiled floors, soft colors and tasteful furnishings. The living room offers soaring ceilings and an iron chandelier as well as richly upholstered fabrics.Ginger Lily is beautifully decorated and boasts ...

Barbados, Hillside, Upper Carlton, St James
7 Bedrooms , 7 Bathrooms
Maximum Occupancy: 14


View Villa Details
From $840.00 Per Night

Gloria's Chateau, Montego Bay

Gloria’s Chateau is a newly built mansion in the prestigious Ironshore Resort Estate. This is a very impressive villa as you enter the solid fanciful security gate of this private residence.As you enter the drive way, you walk up a flight of stairs which reveals a most welcoming swimming pool at the entrance of this house. There are bar facilities around this sparkling blue pool, ready for mixing drinks, relaxing ...

Jamaica, Hillside, Montego Bay
7 Bedrooms , 7 Bathrooms
Maximum Occupancy: 14


View Villa Details
From $3571.43 Per Night

Golden Castle Villa, Montego Bay

In the heart of exotic Montego Bay, Jamaica your fantasy escape is in full regalia. Golden Castle will host you with consummate elegance in our lush tropical ambiance. Ensconced on the majestic Cinnamon Hill Golf Course, Golden Castle, a sprawling new villa, provides breathtaking views of the Caribbean Sea, beautifully appointed with 12 bedrooms and all the accouterments and bucolic grace. The twelve are Air-conditioned with en-suite bathrooms. Ceiling fans ...

Jamaica, Hillside, Montego Bay
12 Bedrooms , 12 Bathrooms
Maximum Occupancy: 24


View Villa Details
From $1714.29 Per Night

Golden Clouds, Oracabessa

Golden Clouds, has one of the highest return guest record, is an outstanding and magical place, renowned for its excellent service staff, luxurious accommodations. This is a spectacular waterfront villa located in the picturesque banana port villa of Oracabessa. This is 15 minutes from Ocho Rios, and your neighbor is Ian Flemming’s famous “Golden Eye” Villa. This property sits on 6 acres and offers a luxurious and private gated estate. ...

Jamaica, Beachfront, Oracabessa
11 Bedrooms , 11 Bathrooms
Maximum Occupancy: 22


View Villa Details
From $5650.00 Per Night

Golden Eye Estate, Oracabessa

GoldenEye is the retreat built by James Bond novelist Ian Fleming in the 1950’s, where he penned 14 of his famous “007” thrillers here. Ian Fleming wrote of his stays at Goldeneye: “….above all, Jamaica has provided a wonderful annual escape from the cold and grime of winters in England, into blazing sunshine, natural beauty, and the most healthy life I could wish to live” Owner Chris Blackwell : “Goldeneye, ...

Jamaica, Beachfront, Oracabessa
12 Bedrooms , 12 Bathrooms
Maximum Occupancy: 24


View Villa Details
From $600.00 Per Night

Grand View, Terres Basses

Breathtaking water views from this beautiful villa perched high on the coastline of Terres Basses.The colorful and generous interior spaces show a creative fusion of the contemporary and the traditional and include a spacious open-plan living and kitchen area with unbroken view over Simpson Bay lagoon to the ocean beyond.Grand View has 6 air-conditioned bedrooms with beautiful en-suite bathrooms. The master suite also has its own lounge area.This is the ...

St. Martin, Hillside, Ocean View, Terres Basses
6 Bedrooms , 6 Bathrooms
Maximum Occupancy: 6


View Villa Details
From $535.71 Per Night

Great Expectations, Estate Chocolate Hole

Perfect for families and groups, Great Expectations features spectacular sunrises and sunsets, short-walk access to swimming and snorkeling at beautiful Hart Bay, and unparalleled vistas of the Caribbean Sea. For tennis enthusiasts, Great Expectations is one of the few villas that boasts its own private court. Great Expectations is comprised of several structures joined by a common patio and pool area. The main building contains the main living/dining area Great Room. ...

St. John, Hillside, Estate Chocolate Hole
8 Bedrooms , 8 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 16


View Villa Details
From $2028.57 Per Night

Greatview, Montego Bay

Greatview is one of the newest and most glamorous private homes overlooking the Half Moon golf course, Ritz Carlton and vast ocean vista. Three world-class golf courses (Cinnamon Hill, Half Moon and White Witch) are within a five-minute drive. Greatview guests have a special membership at the Cinnamon Hill course, entitling them to 50% discounts on 18-hole greens fees, including cart and caddy, and enjoyment of the club restaurant, bar, ...

Jamaica, Hillside, Montego Bay
6 Bedrooms , 6 Bathrooms
Maximum Occupancy: 12


View Villa Details
From $7500.00 Per Night

Greensleeves Villa , St. Peter

Greensleeves, an exclusive vacation villa on a scenic West Coast beachfront headland, has access to two tranquil beaches. Golden bamboo-framed, Mongolian temple doors at the entrance, usher you over a Japanese water garden, brimming with colourful koi. Greenery and tropical flowers, provide an oasis for hummingbirds and whistling frogs.Raised teak walkways and an open-plan design, connect the pond and gardens when moving throughout, with pool and sea views beyond. Eight ...

Barbados, Beachfront, St. Peter
9 Bedrooms , 9 Bathrooms , 2 Half Bathrooms
Maximum Occupancy: 22


View Villa Details
From $1071.43 Per Night

Hammerstein Highland House, Content, Montego Bay

Originally built in the 1940s for English actress Gladys Cooper, the Highland House has long been the site of momentous occasions. Perhaps the most notable moment in history occurred when 2nd owner, broadway legend Oscar Hammerstein II, wrote the lyrics to "The Sound of Music" theme song from the Highland House terrace.Hammerstein and his wife Dorothy purchased the estate as their personal retreat from the fast-paced New York scene. They ...

Jamaica, Hillside, Content, Montego Bay
6 Bedrooms , 6 Bathrooms
Maximum Occupancy: 12


View Villa Details
From $1128.57 Per Night

Hanover House, Montego Bay

If you're not looking for the bells and whistles of modern Caribbean architecture, Hanover House is right for you. Its high ceilings and small treasures from another century evoke the former grandeur and elegance of a dignified past Jamaican lifestyle. When I've had enough of glass block, stainless steel and lucite, this is where I want to be for a week or more every year to remind me of the ...

Jamaica, Hillside, Montego Bay
7 Bedrooms , 5 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 13


View Villa Details
From $928.57 Per Night

Harbour Hill, English Harbour

Harbour Hill is an exclusive Antigua Villa vacation property situated high on a hilltop over looking the Antigua Yacht Club Marina in the centre of English Harbour. The villa has 6 spacious bedrooms, all with their own bathrooms and can accomodate up to 12 guests in perfect comfort. The tastefully furnished bedrooms are all air-conditioned and have ceiling fans. The spacious living area opens onto wide verandas from where you ...

Antigua, Hillside, English Harbour
6 Bedrooms , 7 Bathrooms
Maximum Occupancy: 12


View Villa Details
From $4400.00 Per Night

Harmony, Cove Pond, West End

Harmony, part of Sheriton Estates, located on Anguilla's chic West End, is the newest upmarket villa enclave debuting Thanksgiving 2006. Opening with three of seven planned villas, these oversized havens exude superlative Caribbean elegance. Nestled behind an artfully designed wall, this waterfront property is the privacy-seeker's dream come true. Boasting a fusion of custom-made Asian-Caribbean furnishings, Spanish marble, exotic hardwoods, granite, travertine and other stunning appointments, this is sure to ...

Anguilla, Waterfront, Cove Pond, West End
8 Bedrooms , 9 Bathrooms , 1 Half Bathrooms
Maximum Occupancy: 18


View Villa Details
From $1714.29 Per Night

Hidden Bay by the Sea, North Coast, Runaway Bay

HIDDEN BAY by the SEA perches dramatically on one of the most remarkable sites on Jamaica’s renowned North Coast. Completed in 2014, the property captures both the drama of an extraordinary elevated panorama of blue sea and the proximity of its own sandy beach. Its well-planned design attracts groups of up to 12 adults and especially two- and three- generation families.Brand new 6-bedroom private oceanfront villa overlooking the sea and ...

Jamaica, Oceanfront cliffside, North Coast, Runaway Bay
6 Bedrooms , 6 Bathrooms


View Villa Details
From $600.00 Per Night

Imani Ashia, Ironshore Resort Estate, Montego Bay

Imani Ashia is a 4 bedroom villa plus 2 upper level bedrooms can make a total of 6 bedrooms for large groups. Private pool, views of the Caribbean sea, full staff of cook and housekeeper, gardener. The one thousand acre Ironshore Resort Estate is located in the Rose Hall suburbs of Montego Bay, Jamaica, 15 minutes from the international airport and 20 minutes from the downtown commercial area of Montego Bay. ...

Jamaica, Hillside, Ironshore Resort Estate, Montego Bay
6 Bedrooms , 6 Bathrooms
Maximum Occupancy: 12


View Villa Details

Website Design & Development by Ironistic

Contact a Villa Specialist
X

Not sure where to start your search for a Caribbean villa rental?

Contact a CaribbeanDays villa specialist today! Having visited each and every Caribbean island many times, our specialist can guide you in choosing the right island and villa for your getaway. Fill out the form below to contact a specialist and get started.

  • This field is for validation purposes and should be left unchanged.

Call Now
Contact