Villas and Holiday Homes in Caribbean

1250230 Villas and Holiday Homes in Caribbean

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Caribbean
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Best villa offers in Caribbean

Luxury Villa With A Private Beach! Pool Overlooking The Ocean! - Caribbean
10 5 reviews
Caribbean
10/08 – 20/08
£688/nighttotal: £6880 (10 )

Luxury Villa With A Private Beach! Pool Overlooking The Ocean!

7 2
house, West Bay
Just steps from the world-renowned Seven Mile Beach, this welcoming holiday home is situated in West Bay, offering convenient access, 8.3 kilometers from Owen Roberts International Airport.
This well-appointed villa rental provides complimentary WiFi, a fully equipped kitchen, and accommodation for up to three guests, with a private host ensuring a comfortable stay.
"Dos Coquis" - Walk To The Beach With This Perfect Island Home Away From Home! - Caribbean
9.8 119 reviews
Caribbean
01/10 – 31/10
£142/nighttotal: £4260 (30 )

"Dos Coquis" - Walk To The Beach With This Perfect Island Home Away From Home!

2 2
cottage, Vieques
Located in Vieques' Bravos de Boston neighbourhood, this cottage is just a 2-minute walk from the secluded La Chata beach, offering stunning views of Culebra and Puerto Rico, and is within a 15-kilometre drive of other beautiful island beaches. This 70 square metre villa rental, accommodating up to 4 guests, features air conditioning throughout, a private swimming pool with a lounge deck, a newly renovated kitchen and bathroom, and provides access to beach essentials for a perfect beach house getaway.
Relax Poolside & Walk Or Bike To The Beach From This Amazing Naples Pool Home! - Caribbean
9.3 101 reviews
Caribbean
18/07 – 26/07
£266/nighttotal: £2128 (8 )

Relax Poolside & Walk Or Bike To The Beach From This Amazing Naples Pool Home!

3 4
house, Naples Park
Located in Naples Park, this villa is just 1.2 kilometres from Delnor-Wiggins Pass State Park and 1.7 miles from Vanderbilt Beach, offering a prime position for exploring the local coastline.
This welcoming holiday home boasts 144 square metres of living space with 3 bedrooms, featuring a private swimming pool, Jacuzzi, on-site spa, and garden, alongside a well-equipped kitchen and patio for relaxation.
~Gardenia Cottage~18+ Adult Only Cottage Near Duval St - Caribbean
9.8 6 reviews
Caribbean
18/07 – 26/07
£597/nighttotal: £4776 (8 )

~Gardenia Cottage~18+ Adult Only Cottage Near Duval St

2 4
cottage, Key West
Just 400 meters from Duval Street and Mallory Square, this adults-only cottage is located in the Key West Historic District, offering authentic Key West charm with Dade County Pine and hardwood floors.
This villa rental, accommodating up to four guests in two bedrooms and one bathroom, features a sunny living room with a vaulted ceiling, an open loft sleeping space, a private patio, and access to a shared tropical garden with a large swimming pool.
Nos Soño Stay And Dive, Holidays In Paradise!  Guest Home - Caribbean
10 1 review
Caribbean
11/10 – 18/10
£292/nighttotal: £2044 (7 )

Nos Soño Stay And Dive, Holidays In Paradise! Guest Home

3 2
chalet, Sabana Westpunt
Perfectly situated in Sabana Westpunt, this chalet offers a prime location just 200 meters from Grandi Beach and an 8-minute walk to Kalki Beach, placing you at the heart of local experiences and a short drive from Christoffel and Shete Boka National Parks.
This family-friendly villa rental, accommodating up to 6 guests across 3 bedrooms and 3 bathrooms, boasts a fully equipped kitchen with a dishwasher, air conditioning, a swimming pool, onsite parking, and a BBQ grill, ensuring a comfortable and convenient holiday home experience.
Riverfront House In Port St Lucie With Pool And Dock! - Caribbean
9.6 74 reviews
Caribbean
01/10 – 31/10
£140/nighttotal: £4200 (30 )

Riverfront House In Port St Lucie With Pool And Dock!

4 2
house, Port St. Lucie
Prime riverfront accommodation in Port St. Lucie's desirable River Park district offers a luxury villa experience, situated 13.2 kilometres from Jensen Beach To Jupiter Inlet Aquatic Preserve and 17.7 kilometres from A E Backus Gallery Museum. This welcoming holiday home boasts a private outdoor swimming pool, an on-site spa centre, and a private dock with direct river access, complemented by an equipped kitchen and a spacious living area across 167 square meters.
Palm Breeze Bay Cottage - Caribbean
10 70 reviews
Caribbean
01/08 – 01/08
£227/nighttotal: £82855 (365 )

Palm Breeze Bay Cottage

1 2
cottage, Cooper Jack Bay Settlement
This welcoming cottage is located in Cooper Jack Bay Settlement, Providenciales, offering prime waterfront access with canal views and a boat ramp, just 10 kilometres from the world-renowned Grace Bay beaches, shopping, golf, and restaurants.
This exclusive villa rental boasts a 56 square meter floor area, accommodating up to two guests with one bedroom and one bathroom, and features a private swimming pool with a waterfall, in-cottage laundry facilities, and complimentary kayaks for exploring the local waterways.
Modern 1 Bedroom: "Garden Suite" Amazing Views On Luxury Villa - Caribbean
10 4 reviews
Caribbean
11/10 – 18/10
£108/nighttotal: £756 (7 )

Modern 1 Bedroom: "Garden Suite" Amazing Views On Luxury Villa

1 2
cottage, St Croix
Located in the Christiansted district on the exclusive Little Princess Hill Estate, this villa offers 180-degree views and is situated just 6 kilometers from beaches and 10 kilometers from downtown Christiansted.
This family-friendly cottage, ideal for two guests, boasts a luxurious saltwater swimming pool, a hot tub, and a private deck with a grill, providing exclusive spa treatments and priority access to rental Jeeps for exploring St. Croix.
Beautiful Newly Renovated Golf Front Cottage, Located Inside The Pga National<br><br> - Caribbean
9.8 43 reviews
Caribbean
10/10 – 17/10
£172/nighttotal: £1204 (7 )

Beautiful Newly Renovated Golf Front Cottage, Located Inside The Pga National<br><br>

2 2
cottage, Palm Beach Gardens
Perfectly situated within the exclusive PGA National community, this golf-front cottage offers prime access to the PGA National Resort and Spa, with The Gardens Mall a mere 10-minute drive away and Clematis Street and CityPlace within easy reach.
This welcoming villa rental, boasting two bedrooms and two bathrooms to accommodate up to six guests, features a fully equipped kitchen, complimentary WiFi, air conditioning, a private garden, a swimming pool, and convenient parking, making it an ideal holiday home for exploring the attractions near Palm Beach Gardens.
Uptown Quiet Cottage Close To Beaches, Restaurant & Shopping. - Caribbean
10 8 reviews
Caribbean
01/10 – 31/10
£81/nighttotal: £2430 (30 )

Uptown Quiet Cottage Close To Beaches, Restaurant & Shopping.

1 2
cottage, Key West
Located in the New Town district of Key West, this cottage offers a peaceful retreat just a short taxi or bus ride from Duval Street and attractions such as the Southernmost Point and Ernest Hemingway Home and Museum.
This 41 square meter villa rental, perfect for two guests, features a private swimming pool, a garden, off-street parking, and is situated conveniently close to Florida Keys Beaches and Smathers Beach, making it an excellent holiday home for exploring the area's water sports.
Romey's Villa In Gated Community - Caribbean
9.1 13 reviews
Caribbean
21/08 – 28/08
£137/nighttotal: £959 (7 )

Romey's Villa In Gated Community

1 2
cottage, Christiansted
Located within the exclusive gated Shoy community in Christiansted, this cottage is a mere 300 meters from Shoy Beach and within 10 kilometers of downtown Christiansted, offering convenient access to historical sites like the Christiansted National Historic Site and Steeple Museum.
This welcoming villa rental, boasting 102 square meters of floor area, provides a family-friendly environment with air conditioning, a fully equipped kitchen, and a terrace, whilst its proximity to the golf course and Southgate Coastal Reserve ensures ample leisure activities for guests.
Charming Pga National Getaway -Relax,dine, And Shop In Florida - Caribbean
9.9 173 reviews
Caribbean
03/09 – 12/09
£190/nighttotal: £1710 (9 )

Charming Pga National Getaway -Relax,dine, And Shop In Florida

2 2
cottage, Palm Beach Gardens
Perfectly positioned in PGA National, Palm Beach Gardens, this cottage offers effortless walking access to the PGA National Resort & Spa and is just a 15-minute drive from the beach.
Boasting a 105 square meter floor area, this welcoming villa rental features two bedrooms and two bathrooms, a fully equipped kitchen with new stainless steel appliances, and an outdoor patio with a gas grill, providing a comfortable holiday home experience.

Villas and Holiday Homes with Pool in Caribbean

Among the 1250230 villas in Caribbean here are the 8 best villas with pool

Palm Cottage - Sleeps 4 - Escape The Cold; Our Pool Is Heated! - Caribbean
9.8 54 reviews
Caribbean
18/07 – 26/07
£218/nighttotal: £1744 (8 )

Palm Cottage - Sleeps 4 - Escape The Cold; Our Pool Is Heated!

1 4
cottage, Cudjoe Key
Conveniently located on Summerland Key, this cottage is just 25 kilometres from Key West and a short walk to Tonio's Seafood Shack & Tiki Bar, offering a prime spot for exploring the Florida Keys.
This well-appointed villa rental provides a private, recently renovated standalone unit with a full kitchen and bath, air conditioning, and complimentary WiFi, perfect for up to 3 guests seeking a comfortable holiday home with access to a communal swimming pool and ample parking for boat trailers.
Luxury Golf Villa In Beautiful Lely Resort With Pool - Caribbean
9.9 85 reviews
Caribbean
10/08 – 20/08
£155/nighttotal: £1550 (10 )

Luxury Golf Villa In Beautiful Lely Resort With Pool

2 2
house, Lely Resort
Located in the prestigious Lely Resort, this luxury villa offers proximity to the Gulf of Mexico and is situated approximately 9.8 kilometres from the Collier Museum of the Everglades and 10.1 kilometres from the Naples Botanical Garden.
This exclusive holiday home boasts 143 square metres of living space, featuring air conditioning, complimentary WiFi, a well-equipped kitchen with a dishwasher and microwave, and a private terrace with sea views, alongside access to a communal spa, fitness centre, and tennis court.
74 M² Stuga ∙ 2 Sovrum ∙ 4 Gäster - Caribbean
9.8 41 reviews
Caribbean
01/10 – 31/10
£133/nighttotal: £3990 (30 )

74 M² Stuga ∙ 2 Sovrum ∙ 4 Gäster

2 2
cottage, Jensen Beach
This Hutchinson Island cottage is located in a gated community, offering peek-a-boo water views and direct beach access just across the street, with Jensen Beach Park 1.6 kilometres away and Waveland Beach a mere 500 meters distant.
This family-friendly villa rental, covering 74 square meters with 2 bedrooms and 2 bathrooms for up to 4 guests, boasts a fully equipped kitchen with a dishwasher and island, air conditioning, a swimming pool, garden, fitness centre, and EV charging, making it an ideal holiday home.
La Casita De Charo 2 - Caribbean
Caribbean
01/10 – 31/10
£84/nighttotal: £2520 (30 )

La Casita De Charo 2

1 2
chalet, Constanza
Chalet rental. This accommodation is based in Constanza.
Facilities and services: a swimming pool, a barbecue and a jacuzzi. Take advantage of the Free Parking with this accommodation in Constanza!
Private Oceanfront Cottage With Dockage, Pool Just Minutes To Key West! - Caribbean
8.6 170 reviews
Caribbean
12/10 – 18/10
£174/nighttotal: £1044 (6 )

Private Oceanfront Cottage With Dockage, Pool Just Minutes To Key West!

1 2
cottage, Cudjoe Key
Directly on the oceanfront in Summerland Key, this cottage offers a prime location just 32 kilometres from Key West, with convenient access to Florida Keys Beaches and Coupon Bight Aquatic Preserve.
This welcoming 47 square metre holiday home, perfect for two guests, boasts a full kitchen, air conditioning, a swimming pool, and a private dock, ideal for enjoying water activities like scuba diving and snorkelling.
South Hutchinson Island Cottage With Beach Access! - Caribbean
9.7 75 reviews
Caribbean
21/08 – 28/08
£153/nighttotal: £1071 (7 )

South Hutchinson Island Cottage With Beach Access!

2 2
house, Jensen Beach
Offering direct beach access, this South Hutchinson Island cottage in Jensen Beach is conveniently located 29 kilometres from Fort Pierce City Marina and 34 kilometres from Fort Pierce Inlet State Park.
This two-bedroom villa rental provides 74 square metres of floor area and features a private patio, a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, air conditioning, a swimming pool, a garden, and a spa.
Luxury Studio On The Beach With Pool And Hot Tub - Caribbean
8.6 77 reviews
Caribbean
10/08 – 20/08
£133/nighttotal: £1330 (10 )

Luxury Studio On The Beach With Pool And Hot Tub

1 2
studio, Christiansted
Oceanfront in Christiansted, this newly renovated studio offers island views from its balcony, just a few hundred meters from a communal pool and hot tub, and minutes from downtown Christiansted and popular beaches like Buck Island and Cane Bay. This welcoming villa rental, a luxurious holiday home for two, boasts 60 square meters of living space, a brand-new kitchen with high-end finishes, a modern bathroom, and is perfectly situated for exploring nearby attractions and enjoying water sports.
Waterfront Luxury Villa 34 With Sunset Views And Boat Slip Townhouse - Caribbean
9.8 79 reviews
Caribbean
30/06 – 07/07
£663/nighttotal: £4641 (7 )

Waterfront Luxury Villa 34 With Sunset Views And Boat Slip Townhouse

3 2
house, Marathon
This waterfront villa in Marathon boasts a prime location, offering stunning sunset views and a private boat slip, just 2.7 kilometres from Sunset Park Beach and 10.6 kilometres from Seven Mile Bridge.
This family-friendly holiday home features three bedrooms, three bathrooms, a fully equipped kitchen with a dishwasher and oven, air conditioning, a swimming pool, and on-site parking, with opportunities for cycling nearby and close proximity to Florida Keys Aquarium Encounters.

Frequently Asked Questions about Caribbean

  • What are the must-see attractions that I should visit in the Caribbean?

    For a truly memorable experience in the Caribbean, consider visiting Dunn's River Falls in Jamaica, a stunning terraced waterfall you can climb. In Barbados, a visit to the historic Bridgetown and its Garrison offers a glimpse into colonial history. The Pitons in St. Lucia are iconic volcanic spires offering breathtaking views and excellent hiking opportunities. For underwater exploration, the vibrant coral reefs of Bonaire are a world-renowned diving destination.
  • How much does it typically cost to stay in a villa in the Caribbean?

    Villa rental costs in the Caribbean can vary significantly. A modest two-bedroom villa might range from $200 to $500 per night, while a larger, luxurious property with ocean views and amenities like a private pool could cost $1,000 to $5,000 or more per night. Prices are also influenced by the island, the season, and the specific features of the villa.
  • What are the best towns, villages, or areas to rent a villa in the Caribbean?

    For a diverse range of villa experiences, consider Grace Bay in Turks and Caicos for its pristine beaches and upscale offerings. St. Barts is known for its luxurious villas and exclusive atmosphere. In Antigua, English Harbour provides historical charm alongside beautiful bays. For a more laid-back vibe with stunning natural beauty, consider areas around Soufrière in St. Lucia.
  • When is the best time to book a villa in the Caribbean, and how far in advance should I plan?

    The peak season for the Caribbean is typically from mid-December to mid-April, which also means higher prices. For the best selection and potentially better rates, booking a villa six to nine months in advance is recommended, especially if traveling during this popular period. The shoulder seasons, from late April to June and again from September to November, can offer a good balance of pleasant weather and fewer crowds, with booking 3 to 6 months ahead often sufficient.
  • What are the must-see festivals or seasonal events in the Caribbean?

    The Caribbean hosts vibrant celebrations throughout the year. The Crop Over Festival in Barbados, typically held in July and early August, is a major summer festival with calypso music and parades. Carnival celebrations, particularly in Trinidad and Tobago in February or March, are world-famous for their elaborate costumes and energetic street parties. The St. Lucia Jazz & Arts Festival, usually held in late April or May, attracts international musicians.

Villas in Popular Destinations

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