Villas and Vacation Homes in Caribbean

1782394 Villas and Vacation Homes in Caribbean

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • hometogo
  • expedia
  • belvilla
  • villanovo
  • interhome
  • tripcom
Caribbean
Search for your vacation home
Price per night
Accommodation type
Rating

Best villa offers in Caribbean

Luxury villas in the Caribbean

Expansive cliffside estates, secluded island compounds, and high-end coastal retreats define luxury villas and vacation homes across the Caribbean. From the dramatic volcanic peaks of St. Lucia’s Pitons to the powdery white sands of Turks and Caicos, compare top listings to secure an unforgettable tropical escape.

Vacay Spot Gables 4 To 23 Guest Gameroom 2 Kitchens 2 Bbq, 2 Bar, Backyard, Patio, Prime Loc! 6 Blocks Away From Bars, Nite Clubs, Res, Shops - Caribbean
9.8 261 reviews

Vacay Spot Gables 4 To 23 Guest Gameroom 2 Kitchens 2 Bbq, 2 Bar, Backyard, Patio, Prime Loc! 6 Blocks Away From Bars, Nite Clubs, Res, Shops

house, Miami
Located just 6 blocks from Miami's entertainment districts, this expansive 5-bedroom villa offers prime access to bars, nightclubs, restaurants, and shops, with Cocowalk Shopping Center 1.7 miles away and the Vizcaya Museum 3 miles distant.
This family-friendly holiday home boasts a game room with video games, a terrace with views, a garden, backyard, patio, picnic area, two BBQs, free WiFi, free private parking, and an electric vehicle charging station, ensuring a comfortable and entertaining stay.
Golden Bay 509 - Caribbean
No reviews

Golden Bay 509

house, Sunny Isles Beach
House rental listing. This accommodation is located in Sunny Isles Beach.
Services and facilities: a barbecue, free parking and an elevator. Take advantage of the air conditioning in this house!
Vanderbilt Luxury | Private Pool & Spa | Minutes To Vanderbilt Beach - Caribbean
No reviews

Vanderbilt Luxury | Private Pool & Spa | Minutes To Vanderbilt Beach

house, Naples Park
Located in Naples Park, this welcoming villa is just 1.2 miles from Vanderbilt Beach and 1.4 miles from Delnor-Wiggins Pass State Park, with Naples Municipal Airport 11 miles away.
This holiday home features a year-round outdoor swimming pool, Jacuzzi, air conditioning, and barbecue facilities, perfect for accommodating up to 1 guest with 4 bathrooms.
Privacy Pool Gulf Access And Luxury - Caribbean
9.0 4 reviews

Privacy Pool Gulf Access And Luxury

house, Bonita Springs
This Bonita Springs villa offers gulf access and is conveniently located 7.8 miles from Silverspot Cinema and 16 miles from Tin City, with Southwest Florida International Airport 17 miles away.
This 2010 sq ft holiday home welcomes up to 10 guests with 3 bedrooms, 2 bathrooms, a private pool, garden, on-site casino, and complimentary WiFi.

Villas in Caribbean with private pool

A private pool offers a tranquil space to swim and unwind on your own schedule after a day out on the water. Filter by price and location across leading booking sites to find your ideal poolside retreat, whether nestled in lush hillside gardens or overlooking clear turquoise bays.

Live Like A Local In This Chic Little Cottage With A Private Porch! - Caribbean
10 1 review

Live Like A Local In This Chic Little Cottage With A Private Porch!

cottage, Delray Beach
Located in Seacrest, Delray Beach, this cottage is a 14-minute walk from Putt'n Around and a 2-minute drive to Atlantic Avenue.
This welcoming 750 sq ft holiday home accommodates 4 guests and features 2 bedrooms, 1 bathroom, a full kitchen, free WiFi, an onsite pool, and a BBQ grill, offering a perfect beach house experience.
New Seaside Elegance Luxury Villa In Oyster Pond - December 2024 Renovated - Caribbean
10 1 review

New Seaside Elegance Luxury Villa In Oyster Pond - December 2024 Renovated

house, Oyster Pond
Located in Oyster Pond, this villa is a 3-minute walk to Coralita Beach and 5.6 miles from Grand Case-Espérance Airport.
This recently renovated 1570 sq ft holiday home accommodates up to 15 guests with 4 bedrooms and 3 bathrooms, featuring a private balcony with barbecue, an indoor play area, and bicycle rentals for an enjoyable stay.
Casa Cascada - Caribbean
9.9 201 reviews

Casa Cascada

house
This luxury villa in Sosua, Dominican Republic, is a mere 4-minute drive to Sosua Beach and Alicia Beach, and only 5 minutes from POP Airport, offering unparalleled convenience for your holiday home escape.
Boasting 3 bedrooms and 4 bathrooms to accommodate up to 6 guests, this exclusive property features a private infinity pool, jacuzzi, garden, and a pool table, ensuring entertainment and relaxation during your stay.
Flamboyant Cottage - Spectacular View & Pool - Caribbean
9.8 46 reviews

Flamboyant Cottage - Spectacular View & Pool

cottage, Windward Side
Perched 1,400 feet above sea level on Booby Hill in Windward Side, Flamboyant Cottage offers spectacular Caribbean Sea views and is a 10-minute walk to the village center for groceries, shopping, and restaurants.
This 900 sq ft cottage comfortably accommodates four guests in two bedrooms and features a private pool, a fully equipped kitchen, an outdoor dining gazebo, and is conveniently located near Saba's renowned hiking trails and dive operations, making it an ideal holiday home for adventure and relaxation.

Frequently Asked Questions about Caribbean

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

    When exploring the Caribbean, several attractions stand out. In Barbados, a visit to Harrison's Cave offers a chance to see impressive stalactites and stalagmites. For those in Jamaica, Dunn's River Falls provides a natural wonder where you can climb alongside cascading water. St. Lucia's iconic Pitons, two volcanic spires, are a breathtaking sight and a UNESCO World Heritage site. In Puerto Rico, the El Yunque National Forest is the only tropical rainforest in the U.S. National Forest System and features waterfalls and diverse plant life.
  • How much does it typically cost to stay in a villa in the Caribbean?

    The cost of a villa in the Caribbean can vary quite a bit, generally ranging from around $1,500 per week for a smaller, more basic option to $10,000 or more for a large, luxurious property with amenities like a private pool and staff. Factors like the island, the size of the villa, its proximity to the beach, and the time of year all play a significant role in pricing. During peak season, expect higher rates.
  • What are the best towns, villages, or areas to rent a villa in the Caribbean?

    For villa rentals, many travelers favor areas known for their beautiful beaches and amenities. In Turks and Caicos, Grace Bay is a popular choice for its stunning beach and upscale villas. Barbados offers options in areas like St. James, known for its platinum coast and elegant properties. St. Barts is renowned for its high-end villas and exclusive atmosphere. For a more laid-back vibe, consider areas in Antigua like Jolly Harbour.
  • When is the best time to book a villa in the Caribbean, and how far in advance should I plan?

    Booking a villa in the Caribbean is generally best done well in advance, especially for popular islands and during peak travel times. Planning six to twelve months ahead is advisable for the winter season, which runs from mid-December to mid-April, as this is when many people seek warmer climates. For the shoulder seasons, like late spring or fall, three to six months in advance might suffice, offering potentially better availability and prices.
  • What are the must-see festivals or seasonal events in the Caribbean?

    The Caribbean hosts vibrant festivals throughout the year. Carnival is a major event celebrated across many islands, with spectacular parades and music, notably in Trinidad and Tobago and Barbados (Crop Over). In December, many islands observe Christmas and New Year's with local celebrations and fireworks. The St. Lucia Jazz & Arts Festival, typically held in late April or early May, attracts international artists and showcases local talent.

Villas in Popular Destinations

Pet-friendly villas and vacation homes in Caribbean

Enjoy total peace of mind with fenced yards, spacious single-story layouts, and flexible outdoor spaces that make traveling with pets hassle-free. From quiet island nature paths to dog-approved coastal stretches, search pet-friendly villas and homes so your whole household can join the trip.

Fort Myers Home, Lanai & Private, Heated Pool - Caribbean
No reviews

Fort Myers Home, Lanai & Private, Heated Pool

cottage, Whiskey Creek
Located in Whiskey Creek, this cottage is 0.9 miles from Florida Southwestern State College and within 3 miles of Barbara B Mann Hall and Bell Tower Shops.
This welcoming villa offers a microwave, dishwasher, air conditioning, a swimming pool, and a terrace, with complimentary WiFi and free on-site parking available.
Family Fishing Cottage On The Indian River Lagoon W/250 Ft Dock And Ocean 2 Mil - Caribbean
8.0 13 reviews

Family Fishing Cottage On The Indian River Lagoon W/250 Ft Dock And Ocean 2 Mil

cottage, St. Lucie Village
Directly on the Indian River Lagoon in Fort Pierce's city center, this historic cottage offers direct water access and is just one mile from the inlet for exceptional fishing and one mile from nearby beaches.
This 1000 square foot villa accommodates up to 4 guests with 2 bedrooms and 1 bathroom, featuring a full kitchen, air conditioning, a screened porch, BBQ grill, and a dock with kayaks provided, making it an ideal holiday home for exploring the lagoon.
Casa Pitiusa  Piscina Y Terraza, Las Terrenas - Caribbean
10 1 review

Casa Pitiusa Piscina Y Terraza, Las Terrenas

house
Centrally located in Las Terrenas, this villa is just a 5-minute walk to the beach and within easy reach of numerous restaurants and local amenities.
This welcoming holiday home offers 2 bedrooms, 2 bathrooms, and sleeps up to 4 guests, featuring air conditioning in all bedrooms, a fully equipped kitchen, a private terrace, and access to a shared swimming pool.
Moonstone, Private Room In Villa Casa Blue Pool Sea View - Caribbean
9.7 139 reviews

Moonstone, Private Room In Villa Casa Blue Pool Sea View

house, Koolbaai
Offering stunning "between sky and ocean" views from its terrace and patio, Villa Casa Blue is located in Koolbaai, just 1.9 miles from Princess Juliana International Airport.
This spacious 3-bedroom villa provides a private entrance, a living room, an equipped kitchen with a dishwasher, and access to an on-site casino, swimming pool, and fitness center, making it an ideal holiday home for exploring the outdoor activities in and around Koolbaai.

Family-friendly Caribbean villas

Practical benefits like multiple bedrooms, open gathering spaces, and full kitchens ensure everyone stays relaxed during group getaways and multi-generational vacations. Whether snorkeling along the barrier reef or exploring historic harbor towns, compare top rentals to book a comfortable family base.

One Comfortable Cozy Room $69 Usd Per Night. - Caribbean
9.0 227 reviews

One Comfortable Cozy Room $69 Usd Per Night.

house
Located within the exclusive, secured Mamme Bay resort in Ocho Rios, this villa offers a 5-minute walk to a beautiful beach and is a 10-minute drive from Dunn's River Falls, Dolphin Cove, and Mystic Mountain.
This 270 square feet, 1-bedroom villa, accommodating up to 4 adults, features a private swimming pool, jacuzzi, terrace, garden, and air conditioning, with optional Jamaican cuisine prepared by Chef Chris.
Bahama Gardens - Conch House - Caribbean
No reviews

Bahama Gardens - Conch House

house, Key West
Book this vacation rental. Your accommodation will be based in Key West.
Services and facilities: a fridge, a swimming pool and a washing machine. Take advantage of the jacuzzi in this house.
Lovely 2-bedroom Cottage With Sea Views Located In Exuma, Bahamas - Caribbean
9.8 11 reviews

Lovely 2-bedroom Cottage With Sea Views Located In Exuma, Bahamas

cottage, Hartswell
Spectacular ocean views define this newly constructed cottage in Hartswell, Exuma, located just 20 miles from Georgetown and 30 miles from the airport, with local landmarks like Rolletown Tombs nearby.
This stylish 1100 sq ft villa, a perfect beach house, offers accommodation for 4 guests with 2 bedrooms and 2 bathrooms, featuring a wraparound porch, a full kitchen with a dishwasher, air conditioning, and is only a 5-minute drive to Tropic of Cancer Beach.
Panoramic Views -- 3 Bedrooms 2 Baths + Bonus Room Special Discount May 22-30 - Caribbean
9.8 16 reviews

Panoramic Views -- 3 Bedrooms 2 Baths + Bonus Room Special Discount May 22-30

cottage, Spanish Wells
Located on Russell Island, this cottage offers panoramic views of Pilly Hill Bay and is a short golf cart ride to Spanish Wells, just 0.2 miles from the popular Sandbar Restaurant and multiple beaches.
This 1350 sq ft villa, perfect for up to 7 guests, features 3 bedrooms and 2 bathrooms, a full kitchen, air conditioning, a terrace, garden, spa, and includes 3 kayaks, 2 SUPs, and 3 bicycles for exploring nearby Pink Sand Beach and Current Bay Beach.

Caribbean beachfront vacation homes

Step directly onto world-class shorelines to take in warm ocean breezes, gentle waves, and breathtaking tropical sunsets right outside your door. From iconic destinations like Seven Mile Beach to hidden island coves, compare oceanfront rentals to find a seaside stay at the best rate.

Ohana House - Caribbean
9.2 33 reviews

Ohana House

house, San Andrés
Villa Rot 3 - Caribbean
9.8 77 reviews

Villa Rot 3

house
Villa Entre Boca Chica Y Juan Dolió - Caribbean
10 15 reviews

Villa Entre Boca Chica Y Juan Dolió

house
Ocean Pearl, Nettle Bay Beach Club - Caribbean
9.5 8 reviews

Ocean Pearl, Nettle Bay Beach Club

house, Baie Nettle
copyright © 2026 villapicker.com