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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

Rooftop Pool - Hot Tub - Hollywood Beach Broad - Walk - Caribbean
8.9 19 reviews
Caribbean
17/09 – 21/09
A$223/nighttotal: A$892 (4 )

Rooftop Pool - Hot Tub - Hollywood Beach Broad - Walk

1 2
house , Hollywood
This hotel is located in Hollywood, Florida, just a 3-minute walk from Hollywood Beach and within a 16-kilometre radius of major attractions like Las Olas Boulevard and the International Swimming Hall of Fame. It has consistently received excellent user ratings, making it a popular choice for travellers. The hotel offers comfortable rooms, with each one measuring 37 square metres and accommodating up to 2 guests. With amenities like a beachfront location, an infinity-edge swimming pool, a hot tub, a fitness centre, and free Wi-Fi, guests can enjoy a relaxing and convenient stay.
Villa Au Coeur De Cabarete, 4 Ch, Plage à 100 M - Caribbean
9.9 36 reviews
Caribbean
08/07 – 20/07
A$585/nighttotal: A$7020 (12 )

Villa Au Coeur De Cabarete, 4 Ch, Plage à 100 M

1 8
house , Cabarete
This luxurious four-bedroom villa, part of the Millennium Resort & Spa in Cabarete, Dominican Republic, is located just 0.1 kilometres from the beach and within walking distance of local shops, near the Linares store and Vagamundo.
The 4-bathroom property sleeps eight guests and boasts a private plant-filtered pool, a fully equipped kitchen, 75-inch TV, video projector, trampoline, BBQ, darts, laundry facilities, and access to resort amenities including a swimming pool, sun loungers, and a bar-restaurant.
Penthouse On The Bay 4002 - Caribbean
8.6 14 reviews
Caribbean
27/09 – 04/10
A$241/nighttotal: A$1687 (7 )

Penthouse On The Bay 4002

1 2
house , Bonita Springs
Penthouse On The Bay 4002 is a Bonita Springs holiday home, a short 0.6-kilometre walk from Barefoot Beach and Bonita Beach, offering convenient access to Tin City and Delnor-Wiggins Pass State Park.
This self-catering apartment boasts a 47-square-metre floor area with one bedroom, one bathroom, sleeping up to three guests, and features a private patio, swimming pool access, free Wi-Fi, and on-site parking.
City Condo In Midtown Wynwood With Pool And Parking - Caribbean
9.4 94 reviews
Caribbean
12/10 – 18/10
A$386/nighttotal: A$2316 (6 )

City Condo In Midtown Wynwood With Pool And Parking

1 2
house , Miami
This one-bedroom apartment is located in Midtown Wynwood, Miami, just 3.2 kilometres from the Adrienne Arsht Center for the Performing Arts, placing you within easy reach of the Wynwood Arts District's renowned street art, trendy restaurants, and lively nightlife. The property enjoys excellent user, location, and cleanliness ratings.
The apartment, spanning 65 square metres, comfortably accommodates up to four guests. It features a well-equipped kitchen, a patio, an outdoor swimming pool, a fitness centre, and free Wi-Fi, ensuring a comfortable and convenient stay.

Best Caribbean villas and holiday homes with a kitchen

Hermoso Y Comodo Apartamento Bay Point 303 - Caribbean
8.8 285 reviews
Caribbean
09/11 – 16/11
A$318/nighttotal: A$2226 (7 )

Hermoso Y Comodo Apartamento Bay Point 303

2 2
house , San Andrés
This comfortable house is located in Bay Point, a peaceful area just a short distance from popular attractions like The Hill and Morgan's Cave, making it an ideal base for exploring the island. The property has received very good ratings for cleanliness and user experience, and an excellent rating for location.
The house offers two bedrooms and two bathrooms, providing ample space for families or groups of friends. Guests can enjoy the convenience of a fully equipped kitchen, a private balcony, a swimming pool, a garden, and a spa, as well as free Wi-Fi and parking.
Blue Bay Beach Villa 27 3-min Beach-pool-golf - Caribbean
9.9 81 reviews
Caribbean
06/12 – 20/12
A$454/nighttotal: A$6356 (14 )

Blue Bay Beach Villa 27 3-min Beach-pool-golf

3 5
house , Blue Bay
This villa is situated just a short walk from Blue Bay Beach, offering easy access to the stunning turquoise waters and white sands, and is conveniently located near popular attractions like Queen Emma Bridge and the Curacao Sea Aquarium. The property has received excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The villa offers three bedrooms and two bathrooms, providing ample space for families or groups of friends. Guests can enjoy a range of amenities and activities, including a swimming pool, jacuzzi, spa, fitness centre, tennis court, restaurant, bar, and a private beach area.
Villa In Paradise - Two Seat Golf Cart Now Included With Rental !! - Caribbean
9.8 137 reviews
Caribbean
09/11 – 16/11
A$307/nighttotal: A$2149 (7 )

Villa In Paradise - Two Seat Golf Cart Now Included With Rental !!

2 2
house , Treasure Cay
This beachfront villa in Treasure Cay offers direct access to the sand and sea, and is a short walk (under 2km) from the Lucayan Archipelago and Treasure Cay Marina, with Treasure Cay Golf Course approximately 1.8km away.
The two-bedroom, two-bathroom property sleeps four guests and boasts a fully equipped kitchen, swimming pool, terrace, garden, free Wi-Fi, barbecue, and parking; enjoy nearby watersports and explore the natural beauty of the Lucayan Archipelago.
Soha Suites I - Caribbean
8.9 221 reviews
Caribbean
01/11 – 15/11
A$241/nighttotal: A$3374 (14 )

Soha Suites I

3 6
house , Santiago de los Caballeros
Soha Suites I is located in Santiago de los Caballeros, just 2 kilometres from Leon Center and a short drive from the Monumento a los Heroes de la Restauracion, offering a convenient base for exploring the city. The property has received excellent ratings for location, cleanliness, and overall user experience.
Each suite offers a private bathroom and a balcony in some rooms, ensuring comfort and privacy. Guests can enjoy amenities such as a swimming pool, fitness centre, and free Wi-Fi, as well as a fully equipped kitchen with a fridge, microwave oven, and dishwasher.

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

The Couples Paradise, Close To Downtown, Salt-water Pool - Caribbean
9.6 319 reviews
Caribbean
28/12 – 09/01
A$319/nighttotal: A$3828 (12 )

The Couples Paradise, Close To Downtown, Salt-water Pool

1 3
cottage , West Palm Beach
This charming studio apartment is located just a short distance from the bustling downtown area of West Palm Beach, offering a peaceful retreat while still being close to the city's attractions. It has consistently received excellent ratings for cleanliness, location, and overall guest experience.
The studio features a comfortable bedroom and bathroom, covering a total of 30 square metres. It comes equipped with modern amenities such as a kitchen with a fridge and microwave, air conditioning, Wi-Fi, and a shared swimming pool and garden, perfect for relaxing and enjoying the Florida sunshine.
Sun Caraibes - Caribbean
9.0 92 reviews
Caribbean
14/08 – 21/08
A$299/nighttotal: A$2093 (7 )

Sun Caraibes

1 2
house , Orient Bay
This house is located in Orient Bay, just 6 kilometres from Saint Martin, offering easy access to the beach and the island's main attractions. The accommodation has received excellent ratings for location, cleanliness and user experience, ensuring a comfortable and enjoyable stay.
The house features a kitchen with a fridge and microwave, a swimming pool, a terrace or balcony, a garden, and a tennis court. Guests can also enjoy a concierge service, parking, air conditioning, and direct access to the beach.
The Jazzy Escape - Caribbean
8.9 228 reviews
Caribbean
06/01 – 20/01
A$171/nighttotal: A$2394 (14 )

The Jazzy Escape

2 2
house , Miami Gardens
This two-bedroom house in Miami Gardens is located just 4.3 kilometres from Hard Rock Stadium and within 9.6 kilometres of both Aventura Mall and Calder Casino. The property has received excellent ratings for location, cleanliness and user experience.
The house has a fully equipped kitchen, a garden, a terrace, a swimming pool and a bar. You can enjoy the Florida sunshine on the patio, prepare your own meals and relax by the pool.
Naples Getaway - Caribbean
9.1 129 reviews
Caribbean
08/08 – 18/08
A$306/nighttotal: A$3060 (10 )

Naples Getaway

3 3
house , Naples Park
This property is located in Naples, just 2.2 kilometres from the Silverspot Cinema and 14.8 kilometres from Tin City, providing a peaceful retreat from the hustle and bustle of the city. The house has consistently received excellent reviews for its location, cleanliness, and overall experience.
This three-bedroom home offers a spacious and comfortable layout, perfect for families or groups of friends. Enjoy a range of amenities, including a private beach access, a swimming pool, a spa, and a fitness centre, as well as free bikes to explore the local area.

Best Caribbean villas and holiday homes with jacuzzi

Park Shore Resort 2nd Floor Bldg J - Waterviews - Caribbean
Caribbean
08/08 – 18/08
A$341/nighttotal: A$3410 (10 )

Park Shore Resort 2nd Floor Bldg J - Waterviews

2 3
house , Naples
This 92 square metre, two-bedroom flat is situated in Naples' Park Shore Resort, offering convenient access to attractions such as the Naples Museum Of Art (2.25 kilometres) and Clam Pass Park Beach (2.74 kilometres).
This family-friendly apartment accommodates up to 10 guests and boasts amenities including air conditioning, WiFi, a swimming pool, jacuzzi, fitness centre, tennis court, and a balcony with waterviews, with free private parking also provided.
Casa Blue Pelican. - Caribbean
9.4 16 reviews
Caribbean
06/12 – 20/12
A$641/nighttotal: A$8974 (14 )

Casa Blue Pelican.

3 5
house , Marathon
Casa Blue Pelican, a spacious three-bedroom house in Marathon, Florida, is located a 0.5km walk from Florida Keys Aquarium Encounters and a 1.9km walk from Captain Hook's Marina Dive Center.
This 111 square metre property sleeps up to 15 guests and boasts a fully equipped kitchen, private hot tub, outdoor fireplace, barbecue, and games including billiards and table tennis, plus free Wi-Fi and parking.
Greek-spanish Style Vacation Villa  Getaway - Caribbean
9.4 79 reviews
Caribbean
09/11 – 16/11
A$233/nighttotal: A$1631 (7 )

Greek-spanish Style Vacation Villa Getaway

2 2
house , Rio Grande
This two-bedroom villa is situated within the Wyndham Rio Mar Complex in Río Grande, Puerto Rico, just a short drive from Luquillo Beach and the El Yunque Rainforest. The property has received excellent ratings for its location, cleanliness, and overall experience.
The 113 square metre villa can accommodate up to six guests and features a range of amenities, including a swimming pool, jacuzzi, terrace, garden, and parking. Guests can also enjoy access to the Wyndham Rio Mar Complex's amenities, such as restaurants, a golf course, spa, fitness centre, and various recreational activities.
House ∙ 2 Bedrooms ∙ 6 Guests - Caribbean
Caribbean
06/07 – 13/07
A$347/nighttotal: A$2429 (7 )

House ∙ 2 Bedrooms ∙ 6 Guests

2 3
house , Port St. Lucie
This waterside dwelling is located on Hutchinson Island, offering direct access to the Indian River and the Atlantic Ocean, within the Nettles Island 5-star resort community, approximately 10 kilometres south of Fort Pierce.
This 2-bedroom, 2-bathroom property accommodates up to 6 guests and boasts a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, spa, fitness centre, tennis courts, and direct canal access for fishing, alongside on-site amenities including a marina and restaurant.
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