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Caribbean villas
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102837 Villa rentals in Caribbean

Best Caribbean villas and holiday homes with a pool

Among the 102837 accommodations in Caribbean, here are the 4 best villas and holiday homes with a pool

Villa Victoria - Caribbean
9.6 330 reviews
Caribbean
19/10 – 23/10
A$197/nighttotal: A$788 (4 )

Villa Victoria

2 8
house , Sosúa
Villa Victoria is located in Sosúa, a short distance from both Alicia Beach and Sosúa Beach, making it a great choice for beach lovers. The property has excellent user, location and cleanliness ratings.
The villa offers a range of amenities and activities to ensure a comfortable stay, including a private patio, a fully equipped kitchen, free Wi-Fi, a BBQ grill, a swimming pool, a jacuzzi, and a garden. Guests can also enjoy room service, parking and airport shuttle service.
Naples Park- 97th Ave N - Caribbean
10 39 reviews
Caribbean
11/07 – 18/07
A$557/nighttotal: A$3899 (7 )

Naples Park- 97th Ave N

3 6
house , Naples Park
This Naples Park holiday home on 97th Avenue North is situated 2.9km from Vanderbilt Beach, 3.5km from Delnor-Wiggins Pass State Park, and within walking distance of Silverspot Cinema.
This 131 square metre property boasts a fully equipped kitchen, swimming pool, Jacuzzi, and in-unit laundry facilities, alongside free Wi-Fi and easy access to attractions including Tin City (13.8km) and Naples Municipal Airport (16km).
Vacation Pool Home In The Woods. - Caribbean
9.2 33 reviews
Caribbean
24/08 – 31/08
A$176/nighttotal: A$1232 (7 )

Vacation Pool Home In The Woods.

2 2
house , Golden Gate
This Golden Gate holiday home, near Naples, Florida, is conveniently located approximately 13 kilometres from Naples Municipal Airport, 14 kilometres from Tiburon Golf Club, and 18 kilometres from Tin City.
The 121-square-metre property boasts two bedrooms, one bathroom, sleeps eleven guests, and features a private pool, outdoor fireplace, patio, free Wi-Fi, and free parking.
Cottage With Swimming Pool And Dockage, Just Minutes To Key West! - Caribbean
9.0 314 reviews
Caribbean
15/07 – 18/07
A$316/nighttotal: A$948 (3 )

Cottage With Swimming Pool And Dockage, Just Minutes To Key West!

1 2
cottage , Cudjoe Key
This Cudjoe Key oceanfront cottage offers stunning views and direct beach access, situated within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key.
The 36-square-metre self-catering property sleeps two guests in one bedroom and one bathroom, boasting a fully equipped kitchen, private terrace, swimming pool, and free Wi-Fi.

Best Caribbean villas and holiday homes with a kitchen

Steps To Beach Loiza Getaway With Rooftop Patio! - Caribbean
9.5 30 reviews
Caribbean
19/10 – 23/10
A$452/nighttotal: A$1808 (4 )

Steps To Beach Loiza Getaway With Rooftop Patio!

3 8
apartment , Loiza
This Loíza apartment, an 11-minute walk from Punta Iglesia Beach and 1.6 km from Punta Uvero Beach, offers convenient access to Luis Muñoz Marín International Airport (19 km away).
This three-bedroom, three-bathroom property boasts 139 square metres of space, including a fully equipped kitchen, private balcony, swimming pool, jacuzzi, fitness centre, and parking, comfortably accommodating families or groups.
San San Andrés Magic House 0 By Bbbsai - Caribbean
8.8 7 reviews
Caribbean
17/09 – 21/09
A$89/nighttotal: A$356 (4 )

San San Andrés Magic House 0 By Bbbsai

2 2
house , Buenavista
San San Andrés Magic House 0 is a dwelling located in Buenavista, just a 640-metre walk from Cocoplum Bay Beach, 2 kilometres from Playa Decameron Marazul, and 5.1 kilometres from San Andres Bay. This property offers three bedrooms, accommodating up to five guests, with amenities including air conditioning, a kitchen, Wi-Fi, and parking, and is a non-smoking establishment.
Bonita Springs Condo 4 Mi To Beach Private Patio! - Caribbean
9.6 111 reviews
Caribbean
26/06 – 30/06
A$392/nighttotal: A$1568 (4 )

Bonita Springs Condo 4 Mi To Beach Private Patio!

2 4
apartment , Bonita Springs
This two-bedroom apartment is situated in Bonita Springs, Florida, just 6.4 kilometres from the beach and within easy driving distance of attractions like Silverspot Cinema and Delnor-Wiggins Pass State Park. It has consistently received excellent ratings for user experience, location, and cleanliness.
The 118 square metre apartment comfortably accommodates up to four guests. It offers a range of amenities including a private patio, a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a tennis court, and free Wi-Fi.
La Casita De Mary - Caribbean
8.8 75 reviews
Caribbean
14/09 – 25/09
A$89/nighttotal: A$979 (11 )

La Casita De Mary

2 2
house , Santa Cruz de Barahona
La Casita de Mary, a beachfront property in Santa Cruz de Barahona, offers direct access to Bahoruco Beach.
This two-bedroom, two-bathroom holiday home boasts a 15 square metre floor area, sleeps eight guests, and includes a fully equipped kitchen, Wi-Fi, and a private patio with garden.

Frequently asked questions about villa rentals in Caribbean

  • What are the must-see attractions in the Caribbean?

    The Caribbean boasts incredible diversity! For stunning beaches, you can't miss Grace Bay Beach in Turks and Caicos or Seven Mile Beach in Grand Cayman. History buffs should explore the historic forts in San Juan, Puerto Rico, or the ruins of Port Royal in Jamaica. For natural beauty, the lush rainforests of Dominica and the Pitons in St Lucia are breathtaking. Each island offers something unique, so it really depends on your interests.
  • What are the best villa rentals in Caribbean?

  • Is the Caribbean known for mountains, beaches, forests, or other types of landscapes?

    The Caribbean is incredibly varied. You'll find stunning beaches across many islands, of course. But there are also dramatic mountain ranges, like the Blue Mountains in Jamaica or the volcanic peaks of Montserrat. Lush rainforests thrive in Dominica and other islands, while some islands also feature arid landscapes and even deserts. It's a diverse archipelago.
  • What are the best villa rentals with a pool in Caribbean?

  • What are the most surprising and hidden attractions in the Caribbean?

    Many travellers overlook the smaller islands. Consider exploring Nevis, known for its laid-back atmosphere and pristine beaches, or Anguilla, famed for its unbelievably beautiful Shoal Bay East. Beyond the beaches, the underwater caves of Barbados and the untouched rainforests of Saba offer unique experiences. These lesser-known spots often retain a more authentic Caribbean feel.
  • What are the best villa rentals with a jacuzzi in Caribbean?

    The best villa rentals with a jacuzzi in Caribbean are La Finca Lodge, Jobo 7 Luxury Penthouse - Reserva Conchal and Passion Fruit Lodge.

  • What are some unique ways to learn about the culture of the Caribbean by engaging with its people?

    Attend a local festival, like Crop Over in Barbados or Carnival in Trinidad and Tobago, to experience the vibrant music, dance, and food. Take a cooking class to learn how to prepare traditional dishes. Visit a local market and chat with the vendors – you'll find everyone friendly and willing to share stories. Consider staying in a locally-owned guesthouse rather than a large resort for a more immersive experience.
  • What are the best villa rentals for families and kids in Caribbean?

  • How much time should you set aside to thoroughly explore the Caribbean?

    There's no single answer, as the Caribbean is vast! To properly explore even a few islands, at least two weeks is recommended. A month would allow you to experience more diversity, but even then, you'll only scratch the surface. It really depends on your travel style and how many islands you wish to visit.
  • What are the best pet friendly villa rentals in Caribbean?

  • What cultural experiences or workshops in the Caribbean offer something different?

    Rum distilleries across the islands offer tours and tastings, providing insight into a key part of Caribbean culture. Learning to make traditional crafts, such as pottery or basket weaving, is another great option. Many islands offer workshops on local music and dance, allowing you to actively participate in the culture.
  • What are the best villa rentals with parking in Caribbean?

  • Are there any food festivals in the Caribbean where you can try local food?

    Yes! The Taste of the Caribbean in Miami (although not in the Caribbean itself, it features Caribbean cuisine) showcases the region's culinary talent. Many islands also host smaller, local food festivals throughout the year. Check local event listings for specific dates and locations as these vary.
  • What seasonal natural events, such as migrations or blooming periods, occur in the Caribbean?

    The Caribbean's hurricane season runs from June to November. Whale watching is popular in certain areas during the winter months. Specific blooming periods vary by island and species, but many tropical flowers and plants flourish throughout the year.
  • What exclusive experiences are available when visiting the Caribbean?

    Private yacht charters allow for exploring secluded bays and beaches. Luxury resorts often offer exclusive dining experiences and private villas. Guided hikes through less-visited areas of the rainforests or national parks can provide unique access to the natural beauty of the islands. The possibilities are endless, depending on your budget.

Best Caribbean villas and holiday homes with air conditioning

Aurora Del Mar | Beautiful Tropical Villa In Aguadilla. Grand Patio! - Caribbean
9.4 70 reviews
Caribbean
19/12 – 26/12
A$346/nighttotal: A$2422 (7 )

Aurora Del Mar | Beautiful Tropical Villa In Aguadilla. Grand Patio!

2 4
house , Maleza Baja, Aguadilla, Puerto Rico
This two-bedroom villa is located in Maleza Baja, Aguadilla, just under a kilometre from Survival Beach and within 5 kilometres of Punta Borinquen Golf Club and Martinica Beach.
The property offers a private yard and balcony, a fully equipped kitchen with a refrigerator and microwave, a washing machine and dryer, and barbecue grills for outdoor dining.
Beautiful Paradise In Wellington - Caribbean
9.5 156 reviews
Caribbean
15/07 – 18/07
A$221/nighttotal: A$663 (3 )

Beautiful Paradise In Wellington

1 2
house , Wellington
This Wellington apartment is conveniently located just a short walk from the town centre and within a few miles of Wellington Green Mall, the Palm Beach International Equestrian Center, and the Polo Club. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers a comfortable 63 square metre space, sleeping up to two guests in one bedroom and one bathroom. Amenities include a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, parking, and a shared laundry facility, making it ideal for a relaxing and enjoyable stay.
2 Bed 2 Bath Villa With Jacuzzi, High Speed Wi-fi - Caribbean
9.7 217 reviews
Caribbean
30/11 – 31/12
A$176/nighttotal: A$5456 (31 )

2 Bed 2 Bath Villa With Jacuzzi, High Speed Wi-fi

2 2
house , Sosúa
This villa is located in Sosúa, just 1.6km from Sosúa Beach and 1.4km from Alicia Beach, offering easy access to the beautiful Dominican Republic coastline. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The spacious villa comfortably accommodates up to 6 guests and features 2 bedrooms. Guests can enjoy a range of amenities, including a private swimming pool, a tennis court, a garden, a restaurant, and a children's playground, making it an ideal choice for families or groups seeking a relaxing and enjoyable vacation.
Guest-friendly Room, Pool/wifi/cable Tv/parking - Caribbean
8.6 139 reviews
Caribbean
17/09 – 21/09
A$72/nighttotal: A$288 (4 )

Guest-friendly Room, Pool/wifi/cable Tv/parking

1 2
hotel , Sosúa
This villa is located in Sosúa, just 2 kilometres from Sosua Beach, Coral Reef Casino, and Mundo King Art Museum, offering easy access to the area's attractions. The property has received excellent ratings for location, cleanliness, and overall experience.
The villa offers 4 separate properties, providing privacy and space for larger groups or families. Guests can enjoy a range of amenities, including a swimming pool, spa, fitness centre, and restaurant, as well as free parking and Wi-Fi.

Best Caribbean villas and holiday homes with jacuzzi

Cabaña Tukamping - Caribbean
Caribbean
20/06 – 27/06
A$47/nighttotal: A$329 (7 )

Cabaña Tukamping

1 2
cabin , Minca
This cosy cabin is situated in Santa Marta, just 21 kilometres from Marinka Waterfalls and 11 kilometres from Blue Well, offering easy access to some of the region's most beautiful natural attractions. The cabin is also conveniently located near shopping centres and restaurants, providing everything you need for a comfortable stay.
This charming retreat features one bedroom and one bathroom, comfortably accommodating up to two guests. It offers a range of amenities including Wi-Fi, parking, a spa tub, and easy access to local attractions, making it the perfect choice for a relaxing getaway.
Bright And Airy Fort Myers Home With Pool Access! - Caribbean
10 6 reviews
Caribbean
30/11 – 31/12
A$292/nighttotal: A$9052 (31 )

Bright And Airy Fort Myers Home With Pool Access!

3 2
house , Fort Myers
This holiday home is situated in Fort Myers Villas, just 35 kilometres from Sanibel and Captiva islands and 38 kilometres from the Sanibel Lighthouse, offering easy access to both Fort Myers attractions and the beautiful beaches. The property has received excellent ratings for location, cleanliness, and user experience.
This three-bedroom property spans 146 square metres and comfortably accommodates six guests. The home offers a range of amenities and features, including a private terrace, a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a garden, a spa, a fitness centre, a tennis court, and parking.
Tropical Getaway Spot - Caribbean
8.0 1 review
Caribbean
20/06 – 27/06
A$182/nighttotal: A$1274 (7 )

Tropical Getaway Spot

5 2
house , Port Maria
This five-bedroom villa in Port Maria boasts exceptional elevation, offering panoramic ocean views and proximity to national heritage sites, Jamaica Beaches, and the Blue and John Crow Mountains National Park.
Guests can enjoy a family-friendly stay with amenities including a swimming pool, jacuzzi, air conditioning, and Wi-Fi, with a capacity for ten people and a 11:00 AM check-out time.
Briarwood-1064 Tivoli Dr - Caribbean
10 5 reviews
Caribbean
11/07 – 18/07
A$633/nighttotal: A$4431 (7 )

Briarwood-1064 Tivoli Dr

3 6
house , Naples
This Naples, Florida property, Briarwood-1064 Tivoli Drive, is situated in the Briarwood neighbourhood, approximately 7km from Naples Zoo at Caribbean Gardens and 6.7km from Lowdermilk Beach.
This three-bathroom, 210 square metre house boasts a swimming pool, Jacuzzi, and free Wi-Fi, along with proximity to Naples Municipal Airport (3km) and various marinas.
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