Compare best Airbnb in Caribbean from 100+ providers!

341848 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Caribbean vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Caribbean

Best family friendly Caribbean vacation rentals

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

Second Story Beach Unit, Three Bedrooms, One Baths, Sleeps Up To 4 Guests\n - Caribbean
9.6 54 reviews
Caribbean
07/01 – 07/08
$109/nighttotal: $763 (7 )

Second Story Beach Unit, Three Bedrooms, One Baths, Sleeps Up To 4 Guests\n

1 2
apartment , Vega Baja
This Vega Baja cabin is located just a short walk from the beach in a quiet alley, offering a peaceful escape from the town center. Guests have consistently rated the cabin excellent for cleanliness, location, and overall experience.
The cabin has an open-plan living area and a bedroom that can accommodate up to four guests. Amenities include a kitchen with a fridge and microwave, air conditioning, a terrace, a garden, parking, and access to a shared gazebo with a BBQ.
Pelican's Roost, Waterfront Comfort At Venture Out - Caribbean
8.9 23 reviews
Caribbean
08/27 – 09/05
$318/nighttotal: $2862 (9 )

Pelican's Roost, Waterfront Comfort At Venture Out

2 2
house , Cudjoe Key
This beachfront vacation home in Cudjoe Key is a short drive from both the Ernest Hemingway Home and Museum and Duval Street in Key West, both approximately 23 miles away.
The 860 square foot house boasts two bedrooms, two bathrooms, and can accommodate up to nine guests, offering amenities such as a private pool, hot tub, fitness center, tennis court, and a private beach area.
Tropical Heated Pool Home In Fun Beach Side Town  Sleeps 8 Private - Caribbean
9.8 102 reviews
Caribbean
07/08 – 07/20
$328/nighttotal: $3936 (12 )

Tropical Heated Pool Home In Fun Beach Side Town Sleeps 8 Private

3 8
cottage , Lake Worth
This Lake Worth cottage is located in the Parrot Cove neighborhood, just a short walk from the beach and downtown, making it easy to explore the area's attractions and enjoy the lively atmosphere. It has received excellent user ratings, so you can be sure you're getting a quality stay.
The cottage has 3 bedrooms and 2 bathrooms, providing comfortable accommodation for up to 8 guests. It features a private pool, outdoor grill, and a full kitchen, washer and dryer, and off-street parking for three cars, allowing you to relax and enjoy all the amenities of home.
Bonita Springs Condo 4 Mi To Beach: Private Patio! - Caribbean
9.6 111 reviews
Caribbean
07/06 – 07/13
$245/nighttotal: $1715 (7 )

Bonita Springs Condo 4 Mi To Beach: Private Patio!

2 3
house , Bonita Springs
This ground-floor Bonita Springs apartment is just 4 miles from the beach and a short drive to attractions like Silverspot Cinema and Delnor-Wiggins Pass State Park. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This 2-bedroom, 1270 square foot apartment comfortably accommodates 4 guests. Enjoy amenities like a private patio, a fully equipped kitchen, a swimming pool, a jacuzzi, and a tennis court.

Best Caribbean vacation rentals with a pool

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

Park Shore Resort #355 Lake View, Tennis,  Bike/walk, Gym, Beach, Pickleball - Caribbean
9.6 180 reviews
Caribbean
07/06 – 07/13
$150/nighttotal: $1050 (7 )

Park Shore Resort #355 Lake View, Tennis, Bike/walk, Gym, Beach, Pickleball

2 3
apartment , Naples
This Naples apartment is located in the Park Shore Resort, just a mile from the beach and two blocks from restaurants, grocery stores, and pharmacies. The apartment has received excellent ratings for user experience, location, and cleanliness.
The two-bedroom, two-bathroom apartment offers 840 square feet of living space. This Naples vacation rental provides a range of amenities, including a swimming pool, jacuzzi, spa, fitness center, and parking, as well as a fully equipped kitchen, a terrace, and a washer and dryer.
Shamrock Vanille Orient Bay - Caribbean
9.4 56 reviews
Caribbean
07/05 – 07/12
$155/nighttotal: $1085 (7 )

Shamrock Vanille Orient Bay

1 2
apartment , Orient Bay
Shamrock Vanille Orient Bay, a one-bedroom apartment rental in Orient Bay, St. Martin, is a 12-minute walk from Orient Bay Beach and 1.2 miles from Grand Case-Espérance Airport.
This 430-square-foot (approximately 40-square-meter) unit features a private terrace with pool views, a fully equipped kitchen, and accommodates two guests, offering amenities such as a swimming pool, spa, fitness center, and free parking.
Tropical Beach Bayahibe - Caribbean
9.2 62 reviews
Caribbean
12/28 – 01/09
$80/nighttotal: $960 (12 )

Tropical Beach Bayahibe

1 3
apartment , Bayahibe
Tropical Beach Bayahibe apartment, located in Bayahibe, Dominican Republic, is an 8-minute walk from Bayahibe Beach and 1.8 miles from Dominicus Beach, offering easy access to nearby attractions.
This 560-square-foot rental unit features one bedroom, one bathroom, a fully equipped kitchen, air conditioning, and access to a swimming pool, garden, and free parking; it comfortably sleeps two guests.
Apartamento En Alquiler En Tucacas - Caribbean
Caribbean
12/21 – 12/31
$82/nighttotal: $820 (10 )

Apartamento En Alquiler En Tucacas

1 3
apartment , Tucacas
This apartment in Tucacas is located 1.6 miles from Punta Brava Beach, offering convenient coastal access.
This 1-bedroom, 1-bathroom rental includes air conditioning, WiFi, a full kitchen, and a balcony, with parking available and a capacity for 11 guests.

Frequently Asked Questions about vacation rentals in Caribbean

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

    The Caribbean boasts a wealth of must-see sights. For stunning beaches, you can't beat Grace Bay in Turks and Caicos or Seven Mile Beach in Grand Cayman. History buffs should explore Old San Juan in Puerto Rico, a UNESCO World Heritage site, or the historic forts in Barbados. For breathtaking natural beauty, consider the Pitons in St. Lucia or Dunn's River Falls in Jamaica.
  • What are the best Airbnb and vacation rentals in Caribbean?

  • Are there unique natural phenomena in the Caribbean?

    Absolutely! The Caribbean is home to bioluminescent bays in Puerto Rico and Jamaica, where microorganisms create a magical glow in the water at night. You can also witness volcanic activity in Montserrat or explore the unique coral reefs that surround many islands.
  • What are the most popular Airbnbs in Caribbean?

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

    Pack light clothing, swimwear, sunscreen (high SPF!), insect repellent, a hat, sunglasses, and comfortable walking shoes. Don't forget a reusable water bottle to stay hydrated. Depending on the time of year, a light jacket or sweater for evenings might be useful.
  • What are the best vacation 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 costumes. Trinidad and Tobago's Carnival is world-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 greatly depending on your travel style and the island you visit. A budget traveler might spend $100-$150 per day, while a more luxurious trip could easily cost $500 or more. This includes accommodation, food, local transportation, and some activities. Consider flights separately.
  • What are the best rentals or Airbnbs with a jacuzzi in Caribbean?

    The best vacation rentals or Airbnb with a jacuzzi in Caribbean are Bay Harbor One Vacation, La Finca Lodge and Portofino Tower 3 Unit 1601.

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

    Local restaurants abound! In Jamaica, try jerk chicken or ackee and saltfish. In Cuba, savor ropa vieja or picadillo. Each island has its own unique cuisine. Look for smaller, family-run establishments for an authentic experience. Many hotels also offer restaurants showcasing local flavors.
  • What are some less-famous attractions in the Caribbean that are worth the visit?

    Consider exploring the rainforests of Dominica, hiking to hidden waterfalls in St. Kitts, or visiting the secluded beaches of Culebra, Puerto Rico. Many smaller islands offer a more tranquil and less crowded experience.
  • What are the best activities for engaging with locals and understanding their culture in the Caribbean?

    Attend local festivals, visit farmers' markets, take a cooking class focusing on Caribbean cuisine, or participate in a community-based activity like a beach cleanup. Speaking with locals and asking about their lives and traditions is a great way to deepen your understanding.
  • What unique natural landscapes and terrain features can travelers explore in the Caribbean?

    The Caribbean offers diverse landscapes. Explore lush rainforests, dramatic cliffs, volcanic peaks like those in St. Vincent, pristine beaches, and vibrant coral reefs. Each island has its own unique geological features.
  • How many days are ideal for a trip to the Caribbean, and what are some itinerary suggestions?

    Seven to ten days is a good starting point, allowing you to explore one or two islands in more depth. A possible itinerary could include three days in Puerto Rico exploring Old San Juan and El Yunque National Forest, and four days in the Bahamas relaxing on the beaches and exploring Nassau.

Best Caribbean vacation rentals with a balcony

Hermoso Apartamento Con Piscina A 5 Minutos Del Centro Historico - Caribbean
9.8 73 reviews
Caribbean
01/10 – 03/13
$116/nighttotal: $7192 (62 )

Hermoso Apartamento Con Piscina A 5 Minutos Del Centro Historico

2 2
apartment , Cartagena de Indias
This luxury apartment is located in a peaceful, high-end neighborhood just a 5-minute drive from Cartagena's historic center. The B&B has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers a private pool, perfect for relaxing in the Colombian sun. Guests can enjoy a range of amenities including air conditioning, a fully equipped kitchen, a terrace, a fitness center, and a sauna.
San San Andres Balcony View 4 By Bbbsai - Caribbean
9.3 204 reviews
Caribbean
06/23 – 07/01
$68/nighttotal: $544 (8 )

San San Andres Balcony View 4 By Bbbsai

2 4
apartment , Buenavista
This apartment is conveniently located in Buenavista, just a short drive from both San Luis Beach and San Andres Bay, making it an ideal base for exploring the area. It has consistently received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The apartment offers a private balcony where you can relax and enjoy the views, and a fully equipped kitchen for preparing meals. It also features a refreshing swimming pool, a garden, and a terrace, providing ample opportunities for relaxation and recreation.
Newly Remodeled Beach Access Penthouse Apartment - Caribbean
9.7 194 reviews
Caribbean
12/06 – 12/20
$159/nighttotal: $2226 (14 )

Newly Remodeled Beach Access Penthouse Apartment

2 5
apartment , Loíza
This beachfront rental is located in Medianía Alta, just half a mile from Estudio de Arte Samuel Lind and a short drive from Bahia Beach and Playa Vacia Talega. It has earned excellent ratings for location, cleanliness, and user experience.
The apartment features two bedrooms and two bathrooms, offering comfortable accommodations for a small family or group. Guests can enjoy a range of amenities including a swimming pool, a jacuzzi, a fitness center, a tennis court, and a private balcony with ocean views.
Casa Sierra Maestra (Habitación El Naranjo) - Caribbean
9.0 2 reviews
Caribbean
06/27 – 07/04
$29/nighttotal: $203 (7 )

Casa Sierra Maestra (Habitación El Naranjo)

1 4
house , Bartolomé Masó
Casa Sierra Maestra, a guesthouse in Santo Domingo, offers stunning views of the Yara River and Turquino National Park, providing easy access to hiking and exploring.
This 37-square-foot (340 sq ft converted from square meters) one-bedroom, one-bathroom rental sleeps four, features a kitchen with a fridge, freezer, and microwave, plus a swimming pool, terrace, and parking; enjoy a welcome mojito and organized excursions to Comandancia de la Plata and Pico Turquino, or horseback riding.

Best Caribbean vacation rentals with parking

Stunning Beachfront Penthouse On 19th Floor I Desirable Front Unit - Caribbean
9.0 77 reviews
Caribbean
08/08 – 08/18
$250/nighttotal: $2500 (10 )

Stunning Beachfront Penthouse On 19th Floor I Desirable Front Unit

2 3
apartment , Marco Island
This penthouse condo is located on South Marco Island, just steps from South Marco Beach and a short walk from Tigertail Beach, offering direct beach access. This property receives excellent ratings for user experience, location, and cleanliness.
The two-bedroom condo features a fully equipped kitchen and a private sun terrace. Enjoy amenities like air conditioning, free Wi-Fi, cable TV, a swimming pool, a fitness center, tennis courts, and more.
Tekila Beach,condo Sur La Plage A Saint-martin, Sxm - Caribbean
9.7 63 reviews
Caribbean
08/17 – 08/23
$261/nighttotal: $1566 (6 )

Tekila Beach,condo Sur La Plage A Saint-martin, Sxm

1 4
apartment , Baie Nettle
This beachfront rental in Baie Nettle, Saint Martin, offers direct access to Nettle Bay Beach and is a short walk from Petite Baie and Baie Rouge beaches.
The 700-square-foot (65-square-meter) apartment features a terrace, balcony, private parking, Wi-Fi, a full kitchen with dishwasher, and access to a swimming pool, spa, tennis court, and on-site restaurant.
Dolce Villas At Harmony 2 - Caribbean
9.3 33 reviews
Caribbean
01/10 – 03/13
$69/nighttotal: $4278 (62 )

Dolce Villas At Harmony 2

3 2
apartment , Santiago de los Caballeros
DOLCE VILLAS AT HARMONY 2 is located in a peaceful neighborhood in Santiago de los Caballeros, just a short distance from popular attractions like Monumento a los Heroes de la Restauracion and Leon Center. This apartment has earned excellent ratings for its cleanliness, location, and overall experience.
The 1700 square foot apartment comfortably sleeps up to 6 guests in its 3 bedrooms. Amenities include a fully equipped kitchen, a swimming pool, a garden, a fitness center, and a terrace, making it perfect for families or groups seeking a relaxing and enjoyable stay.
Fully Serviced Apartment At Regatta Living - 2g - Caribbean
8.8 27 reviews
Caribbean
08/17 – 08/24
$80/nighttotal: $560 (7 )

Fully Serviced Apartment At Regatta Living - 2g

1 2
apartment , Santo Domingo
This apartment is located in the Regatta Living complex, just a short drive from the Malecon and within walking distance of the Blue Mall and the Centro Internacional de Cirugia Avanzada. The apartment has excellent user, location, and cleanliness ratings.
The apartment offers a fully equipped kitchen, satellite TV, and comfortable accommodations. Guests can enjoy amenities such as a swimming pool, jacuzzi, fitness center, and spa, as well as access to concierge services and parking.
©2026 cozycozy.com