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Caribbean holiday homes
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136408 Villa rentals in Caribbean

Best Caribbean villas and holiday homes with a pool

Among the 136408 accommodations in Caribbean, here are the 4 best villas and holiday homes with a pool

Estero Beach & Tennis Club #508c - Caribbean
8.0 1 review

Estero Beach & Tennis Club #508c

house, Fort Myers Beach
This apartment at Estero Beach & Tennis Club #508c in Fort Myers Beach is situated 2.4 kilometres from the beach, 37 kilometres from Tin City, and 22.5 kilometres from Delnor-Wiggins Pass State Park.
This 48 square metre apartment accommodates up to 7 guests with 1 bathroom, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, a balcony with sea views, and private parking.
Jupiter Condo W/ Pool Access, Walk To Beach! - Caribbean
9.6 32 reviews

Jupiter Condo W/ Pool Access, Walk To Beach!

house, Jupiter
This Jupiter apartment is located just a short walk from Jupiter Beach, less than 800 metres from the ocean, and within 21 kilometres of both Port of Palm Beach and Rapids Water Park. It has consistently received excellent ratings for location, cleanliness, and user experience.
The two-bedroom apartment offers 116 square metres of space, comfortably accommodating up to four guests. It features a well-equipped kitchen, a relaxing lanai, a private swimming pool, a Jacuzzi, a spa, free Wi-Fi, and parking.
First Floor - End Unit With Lake Views - Caribbean
10 1 review

First Floor - End Unit With Lake Views

house, Naples
This two-bedroom Naples holiday home is situated 7.9 km from Tin City, 1.8 km from the Naples Museum of Art, and 5.5 km from Naples Zoo at Caribbean Gardens, offering convenient access to local attractions.
The 80 square metre property features a fully equipped kitchen, private patio, and can comfortably accommodate up to 10 guests, with added amenities including a swimming pool, fitness centre and air conditioning.
Luxury Old City 4 Bedroom Mansion - Caribbean
9.5 141 reviews

Luxury Old City 4 Bedroom Mansion

apartment, Cartagena
This Cartagena house is located within the historic Walled City, just a short walk from the Walls of Cartagena and Centro Comercial La Serrezuela. The property has received excellent ratings for location, cleanliness and user experience.
This four-bedroom house can comfortably accommodate up to 14 guests and features a fully equipped kitchen, private pool, spa tub, and a garden. Guests can enjoy the convenience of air conditioning, internet access, and a TV, as well as the added benefit of a smoke-free environment.

Best Caribbean villas and holiday homes with a kitchen

Pleasant Condo With Spectacular Views, Pools And Spas - Caribbean
8.3 16 reviews

Pleasant Condo With Spectacular Views, Pools And Spas

house, Marco Island
Anglers Cove J-404, a self-catering property in Marco Island, Florida, is located 5.3km from Marco Island Water Sports, 24km from the Naples Botanical Garden, and 26km from the Collier Museum of the Everglades.
This one-bedroom, one-bathroom holiday home boasts 65 square metres of space, a private balcony, swimming pool, Jacuzzi, tennis court, and free Wi-Fi; guests also benefit from on-site parking.
Beach Paradise Found! Heavenly Views 1/1 Villa Steps Away From Beach And Pool. - Caribbean
9.8 38 reviews

Beach Paradise Found! Heavenly Views 1/1 Villa Steps Away From Beach And Pool.

house, Fort Pierce
This beachfront villa in Fort Pierce, Florida is situated adjacent to a golf course and less than 1.6km from Fort Pierce Beach and Bear Point Sanctuary.
The one-bedroom, one-bathroom property offers a fully equipped kitchen, in-villa laundry, free Wi-Fi, a private balcony, swimming pool, fitness centre, and parking; guests can enjoy nearby Jetty Park Beach and John Brooks Park Riverside, both within 3.2km.
Amazing Villa Steps From The Pool, Incredible Views + Generator - Caribbean
9.6 398 reviews

Amazing Villa Steps From The Pool, Incredible Views + Generator

house, Nazareth
This house is situated on the beach in St. Thomas, just under 2 kilometers from both Wyndham Sugar Bay Beach and Coki Point Beach. The location boasts excellent ratings for user experience, location, and cleanliness.
This 80 square meter property comfortably accommodates up to 4 guests in one bedroom and one bathroom. The house features a fully equipped kitchen, air conditioning, a swimming pool, a spa, a fitness center, parking, and a terrace with a garden, making it perfect for a relaxing and enjoyable stay.
Casa Coco-selva Superior 3 Bedroom @ Casa Linda - Caribbean
9.6 145 reviews

Casa Coco-selva Superior 3 Bedroom @ Casa Linda

house, Sosúa
This property is located in Cabarete, just 5km from Laguna SOV and Encuentro Beach, and within 10km of Sosua Beach and Laguna Beach. It has received excellent ratings for location, cleanliness, and user experience.
The villa is spacious and family-friendly, with a private pool, a jacuzzi, a tennis court, and a garden. Guests can enjoy a range of amenities, including a spa, a concierge service, and free breakfast.

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 of Santo Domingo, Dominican Republic, or the UNESCO World Heritage site of Old San Juan in Puerto Rico. Nature lovers will adore the lush rainforest of Dominica, with its Boiling Lake and Trafalgar Falls, or the underwater wonders of the coral reefs around Barbados.
  • What are the best villa rentals in Caribbean?

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

    The Caribbean's landscape is incredibly varied. You'll find pristine beaches across many islands, of course. However, there are also dramatic volcanic mountains, like those in Dominica and St. Lucia, dense rainforests teeming with wildlife, such as in Jamaica and Puerto Rico, and even arid landscapes like those found in parts of Aruba and Curaçao.
  • What are the best villa rentals with a pool in Caribbean?

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

    Many smaller islands offer hidden gems. Consider exploring the underwater caves of the Bahamas, the secluded beaches of Culebra, Puerto Rico, or the untouched rainforest trails in Montserrat. The Rio Camuy Cave Park in Puerto Rico is another less-visited, yet spectacular, natural wonder.
  • What are the best villa rentals with a jacuzzi in Caribbean?

  • 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 vibrant music and dance. Take a cooking class to learn about Caribbean cuisine and its regional variations. Visit local markets, like the one in Bridgetown, Barbados, to interact with vendors and learn about local produce. Consider staying in a guesthouse or small hotel run by locals 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 and diverse. To truly experience multiple islands and their unique cultures, at least two to three weeks is recommended. However, you could focus on one or two islands for a shorter, more in-depth trip, perhaps a week per island.
  • What are the best pet friendly villa rentals in Caribbean?

  • Is there anything you might not think to pack for the Caribbean?

    Beyond sunscreen and swimwear, consider packing reef-safe sunscreen to protect the coral reefs. Mosquito repellent is essential, especially during the wetter months. A reusable water bottle is a must to stay hydrated, and a light raincoat is useful, as showers can be brief but intense.
  • What are the best villa rentals with parking in Caribbean?

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

    Consider learning to make rum in Barbados, participating in a traditional callaloo preparation workshop in Trinidad and Tobago, or taking a drumming lesson in Cuba. Many islands also offer workshops on local crafts, such as pottery or basket weaving.
  • Are there any food festivals in the Caribbean where you can try local food?

    Yes! Many islands host food festivals. The Taste of Barbados food festival showcases the island's culinary scene. Trinidad and Tobago has Carnival, which features a wide variety of food stalls offering local delicacies. Numerous smaller, local festivals also occur throughout the year.
  • What seasonal natural events, such as migrations or blooming periods, occur in the Caribbean?

    Whale watching tours are popular in certain seasons, particularly in the Dominican Republic. Many Caribbean islands experience blooming periods for various flowers and plants throughout the year, depending on the specific location and species. Sea turtle nesting season varies by island, but generally occurs during the warmer months.
  • What exclusive experiences are available when visiting the Caribbean?

    Luxury resorts offer exclusive experiences like private yacht charters, gourmet dining experiences, and access to private beaches. Some islands offer unique opportunities such as diving with whale sharks (seasonal) or staying in overwater bungalows.

Best Caribbean villas and holiday homes with air conditioning

Lovely Private Cottage, Less Than 5 Miles To The Beach!!! - Caribbean
9.4 15 reviews

Lovely Private Cottage, Less Than 5 Miles To The Beach!!!

cottage, Island Walk
This one-bedroom cottage is situated in the Oaks Estates area of North Naples, approximately 2.4 kilometres from shopping and 8 kilometres from the beach.
The self-catering property features a fully equipped kitchen, an open living area and a private patio with a barbecue, plus complimentary access to a swimming pool and jacuzzi, and comes with beach equipment and kayaks for guest use.
86 M² House ∙ 2 Bedrooms ∙ 5 Guests - Caribbean
No reviews

86 M² House ∙ 2 Bedrooms ∙ 5 Guests

house, Santo Domingo
This charming colonial-style house is located in the heart of Santo Domingo's Colonial Zone, just a short walk from major historical landmarks, museums, and restaurants. The area is alive with history, offering a unique and immersive experience for visitors.
The house itself is a two-bedroom property with one bathroom, spanning 86 square metres and comfortably accommodating up to five guests. The house is equipped with modern amenities, including air conditioning, Wi-Fi, a fully equipped kitchen, and a garden, ensuring a comfortable and enjoyable stay.
Fort Myers Bungalow - 12 Miles To The Beach! - Caribbean
9.8 91 reviews

Fort Myers Bungalow - 12 Miles To The Beach!

house, Villas
This Fort Myers bungalow is situated just 12 miles from the beach, offering easy access to the beautiful coastline, and is also within easy reach of attractions like Tin City, Sanibel and Captiva Chamber of Commerce and Visitors Center, and the Sanibel Lighthouse. The bungalow has received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom property spans 132 square metres and comfortably accommodates up to six guests. The bungalow features a fully equipped kitchen, a spacious living area, and modern amenities including air conditioning, free Wi-Fi, a dishwasher, and an oven, ensuring a pleasant and convenient stay.
Eagles Nest Villa House Ac Tv Wifi Fan Luxury Modern - Caribbean
9.8 6 reviews

Eagles Nest Villa House Ac Tv Wifi Fan Luxury Modern

house, Albion
Eagles Nest Villa, a spacious house in Albion, is located 24 kilometres from Norman Manley International Airport.
This three-bedroom, two-bathroom property boasts 139 square metres of living space, including a private garden with barbecue facilities, free Wi-Fi, and parking, accommodating up to 15 guests.

Best Caribbean villas and holiday homes with jacuzzi

84 M² Villa ∙ 1 Bedroom ∙ 4 Guests - Caribbean
No reviews

84 M² Villa ∙ 1 Bedroom ∙ 4 Guests

house, Port St. Lucie
This villa, situated in Castle Pines at the PGA Village, offers convenient access to Treasure Coast beaches and is within walking distance of Clover Park baseball complex.
Boasting 83 square meters of living space, this one-bedroom, one-bathroom property accommodates up to four guests and features a fully equipped kitchen, air conditioning, a swimming pool, Jacuzzi, spa, and fitness centre.
Villa Atardecer Dorado A 5 Minutos Andando De La Playa - Caribbean
No reviews

Villa Atardecer Dorado A 5 Minutos Andando De La Playa

chalet, Puerto Plata
This pet-friendly holiday home is located in the Isabel de Torres district of Puerto Plata, Dominican Republic, a 0.9km walk from the Taíno Museum of Art and a 1km walk from Saint Philip the Apostle Cathedral.
The 550 square metre property boasts four bedrooms, three bathrooms, and sleeps eight guests, offering a swimming pool, hot tub, fully equipped kitchen, fitness centre, and laundry facilities.
2 Bed 2 Bath Villa With Jacuzzi, High Speed Wi-fi - Caribbean
9.7 151 reviews

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

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.
Hobe Sound Villa W/ Screened Porch: 4 Mi To Beach - Caribbean
9.4 15 reviews

Hobe Sound Villa W/ Screened Porch: 4 Mi To Beach

house, Hobe Sound
This Hobe Sound seaside villa, near Peck Lake Park (1.1 km) and Seabranch Preserve State Park (3.7 km), offers stunning ocean views and proximity to other nature reserves within a 9.7 km radius.
The 106-square-metre property boasts four bedrooms, two bathrooms, sleeps four guests, and includes a jacuzzi, terrace, garden, and fully equipped kitchen with modern appliances; outdoor barbecue facilities are also available.
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