Holiday Rentals in Caribbean

341848 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Caribbean holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Caribbean

Best family friendly Caribbean holiday rentals

Among the 341848 accommodations in Caribbean, here are the 4 best family friendly rentals

San Andrés Espectacular Apto Frente Al Mar, Wi-fi - Caribbean
9.2 123 reviews
Caribbean
17/08 – 23/08
£149/nighttotal: Â£894 (6 )

San Andrés Espectacular Apto Frente Al Mar, Wi-fi

2 4
apartment , San Andrés
This apartment is located in San Andrés, a short distance from the North End (2.7km) and close to the beach, offering stunning ocean views. The apartment has received excellent ratings for user experience, location, and cleanliness.
The apartment is 6 square metres and features a modern kitchen with a fridge and microwave, air conditioning, a swimming pool, a terrace, a garden, and parking. Guests can enjoy a range of activities, including swimming, sunbathing, and exploring the nearby beaches and attractions.
San San Andrés Casa Vacacional 2 By Bbbsai - Caribbean
9.3 147 reviews
Caribbean
20/08 – 24/08
£65/nighttotal: Â£260 (4 )

San San Andrés Casa Vacacional 2 By Bbbsai

2 3
apartment , San Andrés
This apartment is located in San Andrés, just a short walk from Playa Zarpada and 7 km from Cocoplum Bay Beach, offering easy access to the island's main attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is designed for families and features a fully equipped kitchen, a private terrace, a swimming pool, a jacuzzi, and a fitness centre. Guests can also enjoy free Wi-Fi, airport shuttle service, and rental services for bicycles and cars.
Sea-renity - Caribbean
9.0 87 reviews
Caribbean
08/07 – 20/07
£312/nighttotal: Â£3744 (12 )

Sea-renity

4 8
apartment , Philipsburg
Sea-Renity apartments in Philipsburg offer stunning mountain and sea views, a short 0.9-mile walk from Dawn Beach and 9 kilometres from Grand Case–Espérance Airport.
These family-friendly flats, each including a fully equipped kitchen, air conditioning, free Wi-Fi, private parking, and access to a pool, spa and garden, provide comfortable accommodation for your Philipsburg stay.
Apto Los Blancos, A Dos Minuto De Los Patos - Caribbean
9.6 160 reviews
Caribbean
01/07 – 08/07
£29/nighttotal: Â£203 (7 )

Apto Los Blancos, A Dos Minuto De Los Patos

1 2
apartment , Bejuquero
This Bejuquero apartment, near Los Patos and 182 kilometres from Toussaint Louverture International Airport, offers a convenient base for exploring the area.
The 28-square-metre self-catering flat features a bedroom, bathroom, air conditioning, free Wi-Fi, a private terrace with sea views, a swimming pool, parking and sleeps up to two guests.

Best Caribbean holiday rentals with a pool

Among the 341848 accommodations in Caribbean, here are the 4 best rentals with a pool

Caribbean Sea View Apt.on 19 Level, A Serene Stay - Caribbean
9.8 332 reviews
Caribbean
17/08 – 23/08
£106/nighttotal: Â£636 (6 )

Caribbean Sea View Apt.on 19 Level, A Serene Stay

2 4
apartment , Guayacanes
This beachfront apartment is situated in the Juan Dolio-El Pueblo district, 1.8 km from Guayacanes Beach and 2.8 km from Los Marlins Golf Course.
The self-catering flat boasts a fully equipped kitchen, private balcony, in-unit laundry, and access to a swimming pool, sauna, fitness centre, and tennis court; free Wi-Fi is also provided.
Shamrock Orient Bay - Caribbean
9.4 311 reviews
Caribbean
23/06 – 01/07
£158/nighttotal: Â£1264 (8 )

Shamrock Orient Bay

1 4
apartment , Orient Bay
Shamrock Orient Bay apartments are situated in Orient Bay, Saint Martin, a 1.9km stroll from Orient Bay Beach and 1.9km from Grand Case-Espérance Airport.
These self-catering apartments offer a swimming pool, spa, and free Wi-Fi, plus packed lunches for excursions and organised sightseeing tours, all within a peaceful garden setting.
El Conde Del Macao - Caribbean
9.5 34 reviews
Caribbean
27/06 – 04/07
£40/nighttotal: Â£280 (7 )

El Conde Del Macao

2 4
apartment , El Macao
This apartment is situated in El Macao, just 16 kilometres from Cana Bay Golf Club and Punta Blanca, and 22 kilometres from Cocotal Golf and Country Club. The apartment has been highly rated by previous guests, receiving excellent marks for cleanliness and location, and a very good overall rating.
The apartment offers a comfortable 60 square metre space with one bathroom. Guests can enjoy a private pool and garden, a terrace with pool views, a fully equipped kitchen, barbecue facilities, and a range of activities including fishing, bicycle and car rental, and a paid airport shuttle service.
Les Galets Sxm Luxury Lodges - Caribbean
9.3 249 reviews
Caribbean
17/09 – 21/09
£129/nighttotal: Â£516 (4 )

Les Galets Sxm Luxury Lodges

1 2
house , Orient Bay
Les Galets Sxm, near Orient Bay in Saint Martin, offers a self-catering property a 1.9km walk from Orient Bay Beach and 1.9km from Grand Case-Espérance Airport.
This adults-only property features a private entrance, swimming pool, garden, free Wi-Fi, free parking, and well-equipped kitchenettes including microwaves, toasters, fridges, coffee machines, and kettles, plus modern amenities such as flat-screen TVs with streaming services and safety deposit boxes.

Frequently asked questions about holiday rentals in Caribbean

  • What are the must-see sights 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 breathtaking natural beauty, consider the Pitons in St Lucia or the Dunn's River Falls in Jamaica.
  • What are the best Airbnb and holiday rentals in Caribbean?

    Lowest Floor Condo - Oversized Balcony - Beach Front - Reserved Parking Space, Villa Renaissance and Portofino Tower 3 Unit 1601 are the most popular Airbnb and holiday rentals in Caribbean among travellers.

  • Are there unique natural phenomena in the Caribbean?

    Absolutely! The Caribbean is home to bioluminescent bays in Puerto Rico (Mosquito Bay is particularly famous), volcanic landscapes in Martinique and St. Vincent, and vibrant coral reefs teeming with marine life, easily accessible for snorkeling and diving in places like Barbados and the Bahamas.
  • What are the most popular Airbnbs in Caribbean?

  • What essentials should you bring along for a trip to the Caribbean?

    Pack light, breathable clothing, swimwear, sunscreen (high SPF is crucial!), a hat, sunglasses, insect repellent, comfortable walking shoes, and a reusable water bottle. Don't forget any necessary medications and a travel adapter.
  • What are the best holiday rentals with a pool in Caribbean?

  • What famous events or festivals are happening in the Caribbean?

    Carnival celebrations are huge across the Caribbean, with vibrant parades and music. Trinidad and Tobago's Carnival is particularly renowned. Other notable events include Crop Over in Barbados and Junkanoo in the Bahamas.
  • What are the best rentals for families and kids in Caribbean?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in the Caribbean?

    Daily budgets vary wildly depending on your travel style and the island. A budget-conscious traveller might manage on £100 per day, while a luxury trip could easily cost £500 or more. This includes accommodation, meals, local transport, and some activities.
  • What are the best rentals or Airbnbs with a jacuzzi in Caribbean?

  • Where can you find the best restaurants serving local dishes in the Caribbean, and what are the must-try specialties?

    Each island has its culinary gems. In Jamaica, try jerk chicken; in Cuba, ropa vieja; in Barbados, flying fish; and in the Dominican Republic, la bandera. Look for local restaurants away from the main tourist areas for more authentic experiences. Many islands also have fantastic street food scenes.
  • What are some less-famous attractions in the Caribbean that are worth a visit?

    Consider exploring the lesser-known islands like Dominica, known for its lush rainforests and hiking trails, or explore the beautiful beaches and laid-back atmosphere of Culebra, Puerto Rico. Many smaller islands offer a more secluded and authentic Caribbean experience.
  • What are the best activities for engaging with locals and understanding their culture in the Caribbean?

    Visit local markets, attend community events, take a cooking class focusing on Caribbean cuisine, or try a local craft workshop. Many islands offer opportunities to interact with locals through guided tours or community-based tourism initiatives.
  • What unique natural landscapes and terrain features can travellers explore in the Caribbean?

    The Caribbean's diverse geography offers everything from pristine beaches and lush rainforests to volcanic peaks and dramatic cliffs. Explore the John Crow Mountains National Park in Jamaica, the cloud forests of Dominica, or the unique rock formations of El Yunque National Forest in Puerto Rico.
  • How many days are ideal for exploring the Caribbean, and what are some itinerary suggestions?

    The ideal trip length depends on your interests. A week allows for exploring one or two islands in depth. Two weeks enables a more relaxed pace and the opportunity to visit three or more islands. Consider focusing on a specific island group (e.g., the Lesser Antilles) or choosing islands with contrasting experiences (e.g., a beach island and a more adventurous island).

Best Caribbean holiday rentals with a balcony

Very Private Downtown Sosua Apartment  Large Pool  Weekly Maid - Caribbean
9.7 53 reviews
Caribbean
14/08 – 21/08
£46/nighttotal: Â£322 (7 )

Very Private Downtown Sosua Apartment Large Pool Weekly Maid

1 2
apartment , Sosùa
This apartment is conveniently located in Sosúa, just a 15-minute walk from both Sosúa Jewish Museum and Sosúa Beach, offering easy access to the town's attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment spans 65 square metres and comfortably accommodates two guests in one bedroom. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, terrace, garden, and concierge services, ensuring a comfortable and enjoyable stay.
Family-friendly Palm River Estates House! - Caribbean
9.9 48 reviews
Caribbean
08/07 – 20/07
£338/nighttotal: Â£4056 (12 )

Family-friendly Palm River Estates House!

3 8
house , Naples Park
This family-friendly house is situated in Naples, just 19 kilometres from Tin City and 6 kilometres from Silverspot Cinema, offering a relaxing escape close to attractions. The property has consistently received excellent ratings from previous guests for its cleanliness, location and overall experience.
The three-bedroom house, spanning 171 square metres, comfortably accommodates up to eight guests. Enjoy a range of amenities including a fully-equipped kitchen, private terrace, a swimming pool and a jacuzzi, perfect for a relaxing stay.
Casa Kamanda, Zona Colonial, Santo Domingo - Caribbean
9.0 130 reviews
Caribbean
12/10 – 18/10
£31/nighttotal: Â£186 (6 )

Casa Kamanda, Zona Colonial, Santo Domingo

1 2
apartment , Santo Domingo
Casa Kamanda, a family-friendly apartment in Santo Domingo's Zona Colonial, is ideally situated near Montesinos Palace, Guibia Beach, and Puerto Santo Domingo.
This pet-friendly dwelling boasts a private patio, garden access, a well-equipped kitchen including a fridge, freezer and microwave, free Wi-Fi, air conditioning, and flat-screen TVs with streaming services.
Sunny Stays Vacation Rental In Southwest Florida! - Caribbean
10 2 reviews
Caribbean
27/08 – 05/09
£137/nighttotal: Â£1233 (9 )

Sunny Stays Vacation Rental In Southwest Florida!

3 2
house , Lehigh Acres
This three-bedroom holiday home in Lehigh Acres, Southwest Florida, is conveniently located approximately 21 kilometres from Southwest Florida International Airport.
The 149-square-metre property boasts two bathrooms, sleeps up to eleven guests, and includes a fully equipped kitchen with dishwasher, private terrace, in-unit laundry, and free Wi-Fi.

Best Caribbean holiday rentals with parking

Beautiful, Spacious, Family Friendly Private Home! One - Caribbean
9.4 93 reviews
Caribbean
28/12 – 09/01
£122/nighttotal: Â£1464 (12 )

Beautiful, Spacious, Family Friendly Private Home! One

4 3
apartment , Port St. Lucie
This four-bedroom house is conveniently located in Port St. Lucie, just a short drive from Woodlands Trails Park and other popular attractions. It has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The property is spacious and comfortably accommodates up to 10 guests. Enjoy a range of amenities including a fully equipped kitchen, a relaxing garden, a private patio, and a spa, perfect for a memorable stay in Port St. Lucie.
Beachfront Apartment, Quiet 4 Beds, 1 Bath, Ac, Wi-fi, Hot Water, In Paraiso Near Los Patos - Caribbean
9.2 169 reviews
Caribbean
28/12 – 09/01
£71/nighttotal: Â£852 (12 )

Beachfront Apartment, Quiet 4 Beds, 1 Bath, Ac, Wi-fi, Hot Water, In Paraiso Near Los Patos

3 3
apartment , Paraíso
This beachfront apartment in Paraíso, near Paraíso Beach and Los Patos, offers stunning sea views and is ideally located for exploring the area.
The 80-square-metre property features three bedrooms, a living room, a fully equipped kitchen, a private terrace, a swimming pool, parking, and free Wi-Fi; it comfortably accommodates families and provides an indoor play area.
Fuentes House - Caribbean
9.4 34 reviews
Caribbean
08/07 – 20/07
£111/nighttotal: Â£1332 (12 )

Fuentes House

4 8
apartment , San Andrés
Fuentes House is located in San Andrés, just a short distance from Spratt Bight Beach and Playa Decameron Marazul, offering easy access to some of the island's most beautiful beaches. The apartment has consistently received excellent ratings for cleanliness, location, and overall experience.
This two-bedroom, one-bathroom apartment is ideal for families or groups of up to four people. It comes equipped with a kitchen, air conditioning, a terrace, and a garden, making it perfect for enjoying a relaxing stay in San Andrés. You can also take advantage of the free Wi-Fi, private entrance, and nearby sightseeing tours.
Pool+hot Tub+sauna+gym! 1 Minute Walk To Beach! - Caribbean
9.5 123 reviews
Caribbean
01/11 – 15/11
£307/nighttotal: Â£4298 (14 )

Pool+hot Tub+sauna+gym! 1 Minute Walk To Beach!

4 6
apartment , Pompano Beach
This four-bedroom house is situated in Pompano Beach, less than 1.6km from Pompano Beach and the Hillsboro Inlet Lighthouse.
The property features a private fenced yard, a swimming pool, a fitness centre, a sauna, a spa, and a fully equipped kitchen, ideal for families or groups of up to eight people.
©2026 cozycozy.com