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Caribbean holiday homes
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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

Coral Falls Of Lely W Tiki Huts & Heated Pool - Caribbean
9.6 38 reviews
Caribbean
06/07 – 13/07
NZ$299/nighttotal: NZ$2093 (7 )

Coral Falls Of Lely W Tiki Huts & Heated Pool

2 3
house , Lely Resort
This two-bedroom holiday home in the Coral Falls of Lely Resort, Florida, is conveniently located approximately 14 kilometres from Tin City, 10 kilometres from the Naples Botanical Garden, and 11 kilometres from the Collier Museum of the Everglades.
The 130 square metre property features a fully equipped kitchen, private patio, swimming pool, Jacuzzi, and parking, sleeping up to four guests and offering easy access to local cycling routes.
Lovely Beachfront House With Amazing View In Lagun - Caribbean
9.9 107 reviews
Caribbean
30/07 – 03/08
NZ$318/nighttotal: NZ$1272 (4 )

Lovely Beachfront House With Amazing View In Lagun

1 2
house , Lagun
This semi-detached house, situated in Curaçao's Banda Abou district within the Lagoon Ocean Resort, is a one-minute walk from a sandy beach and a short drive from popular beaches such as Grote Knip and Playa Kalki.
Offering a king-size bed, two bathrooms, and a well-equipped kitchen including a fridge, freezer, microwave, and Senseo coffee machine, this one-bedroom property sleeps four guests and boasts a private patio with sea views, plus access to a shared swimming pool.
Tranquility Villa - Caribbean
9.4 33 reviews
Caribbean
26/06 – 29/06
NZ$536/nighttotal: NZ$1608 (3 )

Tranquility Villa

2 1
house , Port Antonio
Tranquility Villa is located in Port Antonio, a short distance from the city centre and close to East Harbour. This property has received excellent ratings for its location, cleanliness, and overall experience.
The villa offers two bedrooms and one bathroom, spanning 111 square metres. Guests can enjoy a range of amenities including a private swimming pool, tennis court, and access to concierge and room service, as well as panoramic ocean views from the terrace.
Luxurious Cabin Retreat In Las Jarabacoa With Private Pool, El Reloj Se Detuvo - Caribbean
Caribbean
10/01 – 13/03
NZ$1117/nighttotal: NZ$69254 (62 )

Luxurious Cabin Retreat In Las Jarabacoa With Private Pool, El Reloj Se Detuvo

5 2
cabin , Las Guázaras
This spacious five-bedroom, five-bathroom lodge, suitable for up to sixteen guests, is located in the tranquil Las Guázaras, Dominican Republic, offering convenient access to hiking trails and waterfalls.
This wheelchair-accessible property boasts 500 square meters of living space, featuring a fully equipped kitchen, air conditioning, a private swimming pool, and a garden with outdoor seating, ensuring a comfortable stay for families and pets.

Best Caribbean villas and holiday homes with a kitchen

Spacious Naples Home Less Than 1 Mi To Vanderbilt Beach! - Caribbean
9.3 54 reviews
Caribbean
20/11 – 30/11
NZ$552/nighttotal: NZ$5520 (10 )

Spacious Naples Home Less Than 1 Mi To Vanderbilt Beach!

3 4
house , Naples Park
This property is situated in Naples Park, just 1.3 km from Vanderbilt Beach and 14.6 km from Tin City, offering easy access to both the beach and local attractions. It has consistently received excellent user and location ratings, and a very good cleanliness rating.
This spacious home spans 195 square metres and comfortably accommodates up to 10 guests across three bedrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private garden, a tennis court, and a terrace with garden views.
Chic Naples Retreat With Private Heated Pool And Lanai - Caribbean
10 144 reviews
Caribbean
01/11 – 15/11
NZ$516/nighttotal: NZ$7224 (14 )

Chic Naples Retreat With Private Heated Pool And Lanai

3 6
house , Naples Park
This comfortable house is located in Naples, Florida, just 2.1 kilometres from Silverspot Cinema and 2.9 kilometres from Delnor-Wiggins Pass State Park. The property has received excellent reviews for its location, cleanliness, and overall user experience.
The three-bedroom house spans 191 square metres and includes a fully equipped kitchen, a private heated pool with a lanai, and a garden. Guests can enjoy free bikes, Wi-Fi, and a range of entertainment options, including television and video games.
Beach And Golf Private Villa In Palmas Del Mar - Caribbean
9.8 350 reviews
Caribbean
10/08 – 17/08
NZ$298/nighttotal: NZ$2086 (7 )

Beach And Golf Private Villa In Palmas Del Mar

1 4
house , Palmas Del Mar
This beachfront property is located in Humacao, just a short walk from Palmas del Mar Beach and a short drive from the Palmas Del Mar Golf Club. The house has received excellent ratings for its location, cleanliness, and overall experience, making it an ideal choice for a relaxing and enjoyable stay.
The house offers one bedroom and one bathroom, spanning across 87 square metres. It features a fully equipped kitchen, a private pool, a terrace, a garden, and direct access to the beach, ensuring a comfortable and enjoyable stay for families and groups.
Private Tropical Villa With Breathtaking Views! - Caribbean
9.3 8 reviews
Caribbean
27/08 – 05/09
NZ$336/nighttotal: NZ$3024 (9 )

Private Tropical Villa With Breathtaking Views!

1 2
cottage , Christiansted
This one-bedroom house is situated in a peaceful neighbourhood just 8 kilometres from Christiansted, the historical capital of Saint Croix, offering easy access to shops, restaurants, and attractions.
The house features a patio with stunning views, a garden, and parking, perfect for a couple seeking a relaxing retreat with easy access to the island's attractions.

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

Beautiful, Cozy Beach Villa In The Heart Of Treasure Cay! - Caribbean
9.9 52 reviews
Caribbean
21/12 – 31/12
NZ$486/nighttotal: NZ$4860 (10 )

Beautiful, Cozy Beach Villa In The Heart Of Treasure Cay!

2 3
house , Treasure Cay
This beachfront villa in Treasure Cay offers prime access to Lucayan Archipelago, Treasure Cay Beach, and Treasure Cay Marina, all within a 5-minute walk, and Treasure Cay Golf Course is 1.8km away.
This 88 square metre property sleeps six guests in two bedrooms and two bathrooms, boasting a private patio, swimming pool, tennis court, and fully equipped kitchen including a dishwasher, alongside free Wi-Fi.
Golf View Rio Mar Villa - Caribbean
9.5 109 reviews
Caribbean
20/11 – 30/11
NZ$359/nighttotal: NZ$3590 (10 )

Golf View Rio Mar Villa

1 2
house , Río Grande
This villa is located in Mameyes II, just a short walk from Luquillo Beach and the Wyndham Rio Mar Casino, with the Wyndham Rio Mar Golf Course and Carabali Rainforest Park within 5km. The accommodation has received excellent ratings for its location, cleanliness, and overall experience.
The property is a 1-bedroom, 1-bathroom villa with a floor area of 74 square metres, suitable for a maximum of 2 guests. It features a private pool, spa, tennis court, and a fully equipped kitchen, making it ideal for a relaxing and enjoyable stay.
The Villas On Great Bay, Villa Lavinia #9 - Caribbean
9.8 183 reviews
Caribbean
20/11 – 30/11
NZ$557/nighttotal: NZ$5570 (10 )

The Villas On Great Bay, Villa Lavinia #9

2 4
house , Philipsburg
Villa Lavinia #9, in Philipsburg, offers direct beachfront access to Great Bay Beach and is a 2.1km walk from Little Bay Beach, with Princess Juliana International Airport 7km away.
This 121 square metre property boasts a spacious layout with two bedrooms, three bathrooms, a living room, and an array of amenities including a private patio, infinity pool, jacuzzi, and on-site parking; perfect for families seeking a luxurious Caribbean getaway.
Marlin Bay Resort & Marina Managed By Elite Alliance Hospitality - Caribbean
9.9 1011 reviews
Caribbean
08/07 – 20/07
NZ$1140/nighttotal: NZ$13680 (12 )

Marlin Bay Resort & Marina Managed By Elite Alliance Hospitality

3 8
house , Marathon
This house in Marathon, Florida is conveniently located just a short drive from attractions like the Florida Keys Aquarium Encounters and Captain Hook's Marina Dive Center. The property has consistently received excellent ratings for location, cleanliness, and user experience.
The house features a terrace, a well-equipped kitchen, a private bathroom with amenities, and a dining area. It offers a range of amenities, including a swimming pool, a Jacuzzi, a sauna, a spa, a fitness centre, a tennis court, and free parking.

Best Caribbean villas and holiday homes with jacuzzi

Villa Marioly - Caribbean
Caribbean
26/06 – 29/06
NZ$366/nighttotal: NZ$1098 (3 )

Villa Marioly

2 1
house , Angostura
This villa in Imbert is located 48 kilometres from Amber Cove and 32 kilometres from the 27 Waterfalls, with proximity to the Amber Museum, Museum of Taino Art, Templo de Las Americas, and Fort San Felipe.
This property offers accommodation for up to six guests, featuring two bedrooms, one bathroom, a full kitchen with a fridge, and a Jacuzzi, with laundry facilities and Wi-Fi also provided.
Jupiter Condo With Pool Access, Walk To Beach! - Caribbean
9.6 30 reviews
Caribbean
17/08 – 23/08
NZ$375/nighttotal: NZ$2250 (6 )

Jupiter Condo With Pool Access, Walk To Beach!

2 4
apartment , 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.
Tropical Naples Hideaway - 1 Mi To Beaches! - Caribbean
9.8 62 reviews
Caribbean
08/07 – 20/07
NZ$779/nighttotal: NZ$9348 (12 )

Tropical Naples Hideaway - 1 Mi To Beaches!

3 8
house , Naples Park
This Naples Park holiday home is conveniently located approximately 1.6km from Vanderbilt Beach and a short 2.9km drive from Tin City, offering easy access to Delnor-Wiggins Pass State Park.
The 177 square metre property boasts three bedrooms, two bathrooms, a private pool and hot tub, plus a fully equipped kitchen including a dishwasher and microwave, ideal for families or groups.
Cayman Luxury Rentals At One Canal Point - Caribbean
9.5 105 reviews
Caribbean
20/11 – 30/11
NZ$786/nighttotal: NZ$7860 (10 )

Cayman Luxury Rentals At One Canal Point

2 4
house , Upper Land
This house is situated in Upper Land, Grand Cayman, just a short distance from Seven Mile Beach and a convenient 3.7 miles from Owen Roberts International Airport. The house enjoys a peaceful location in Upper Land, offering a tranquil escape from the busier tourist areas. It has consistently received excellent ratings for its cleanliness, location, and user experience.
The house spans 324 square metres and is ideal for families or groups. It offers a range of amenities including a swimming pool, jacuzzi, terrace, garden, fitness centre, and private parking. The house is also equipped with a modern kitchen, air conditioning, and internet access.
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