Holiday Rentals in Caribbean

491001 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 491001 accommodations in Caribbean, here are the 4 best family friendly rentals

San San Andrés Casa Vacacional 2 By Bbbsai - Caribbean
9.3 153 reviews

San San Andrés Casa Vacacional 2 By Bbbsai

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.
Sweet Breeze - Caribbean
9.5 364 reviews

Sweet Breeze

apartment, San Andrés
SWEET BREEZE is a one-bedroom apartment located in San Andrés, just 1 kilometre from the Gustavo Rojas Pinilla International Airport and a short distance from the island's North End. The apartment has received excellent ratings for cleanliness and location, and guests consistently praise its family-friendly atmosphere.
The apartment features a well-equipped kitchen, a private terrace, and air conditioning for your comfort. Guests can enjoy garden views and relax in the outdoor space, take advantage of the swimming pool, or explore the nearby beaches such as Spratt Bight and Parceras.
4 Bedroom Private Villa In The Heart Of Sosua, An Escape To Paradise. - Caribbean
9.2 15 reviews

4 Bedroom Private Villa In The Heart Of Sosua, An Escape To Paradise.

house, Sosua
This house is located in Sosua, just 1.6km from Laguna SOV and 2.3km from Sosua Beach, making it an ideal base for exploring the area. It has received excellent user ratings, suggesting a comfortable and enjoyable stay.
The property has four bedrooms and three bathrooms, spanning 279 square metres and accommodating up to eight guests. It features a private pool, fireplace, fully equipped kitchen, washing machine, barbecue grills, and housekeeping on request, ensuring a relaxing and convenient stay.
Las Palmas - Caribbean
10 3 reviews

Las Palmas

apartment, Santiago de los Caballeros
This three-bedroom flat in Las Palmas, Santiago de los Caballeros, offers convenient access to attractions including Leon Center (3.4 km), La Aurora Cigar Factory (3.2 km), and Monumento a los Heroes de la Restauracion (6.9 km).
This 82 square metre apartment accommodates up to 11 guests and features a balcony with mountain views, complimentary on-site parking, free WiFi, a garden, and an on-site mini-market.

Best Caribbean holiday rentals with a pool

Among the 491001 accommodations in Caribbean, here are the 4 best rentals with a pool

Casa Magua Las Galeras - Caribbean
9.8 62 reviews

Casa Magua Las Galeras

house
Casa Maguá, a private villa in Las Galeras, Samaná, is situated approximately 4.4km from La Playita and Playa Grande beaches.
This four-bedroom, four-bathroom property sleeps eight guests and boasts an infinity pool, jacuzzi, fully equipped kitchen, daily breakfast, and 24/7 security, all within easy reach of Las Galeras town and its amenities.
2 Room Apartment, Pool, Balcony, Bbq, Kitchen - Caribbean
9.7 71 reviews

2 Room Apartment, Pool, Balcony, Bbq, Kitchen

apartment, Boca Chica
This two-bedroom Boca Chica apartment is situated 0.4km from Boca Chica beach, a 5-minute walk from local restaurants and shops, and a 14-minute drive from Las Américas International Airport.
The 72 square metre flat offers a fully equipped kitchen, private balcony, access to a swimming pool, fitness centre and parking, comfortably sleeping up to six guests.
New Grenada Suite - Parking Pool & Pets 209 - Caribbean
9.1 115 reviews

New Grenada Suite - Parking Pool & Pets 209

house, Key West
The NEW Grenada Suite is located in Key West, just a short drive from Duval Street and Mallory Square, offering a peaceful retreat while still being close to the action. The property has consistently received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
This two-bedroom property can accommodate up to six guests, making it ideal for families or groups of friends. The house offers a range of amenities including a private pool, a jacuzzi, a fully equipped kitchen, and a fitness centre, ensuring a comfortable and enjoyable stay.
Penthouse  Pvt Rooftop  200mb Wifi  Buenavista - Caribbean
10 14 reviews

Penthouse Pvt Rooftop 200mb Wifi Buenavista

apartment
This modern 3-storey penthouse is situated in Barranquilla, just 200 metres from prominent shopping centres including Buenavista, Mallplaza, and Plaza del Parque.
This family-friendly apartment offers 2 bedrooms and sleeps 3 guests, featuring a private 56 square metre rooftop terrace with a swimming pool, air conditioning throughout, and a fully equipped kitchen with a dishwasher, whilst being a 20-minute drive to the beaches of Puerto Colombia.

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

Beach Paradise Apartments - Caribbean
9.5 83 reviews

Beach Paradise Apartments

apartment, San Andrés
Beach Paradise Apartments are located in the Los Almendros neighbourhood, just 1 kilometre from Gustavo Rojas Pinilla International Airport, offering a peaceful retreat close to the beach. The apartment has received excellent ratings for cleanliness and user experience, with a very good location rating.
This self-catering property features a private terrace, a fully equipped kitchen with a microwave, fridge, and stovetop, and comfortable bedding with towels and linen provided. Guests can also enjoy satellite TV, air conditioning, and parking.
2 Bedrooms At Baia Residences - Caribbean
9.9 25 reviews

2 Bedrooms At Baia Residences

apartment, Santiago de los Caballeros
Baia Residences, a Santiago de los Caballeros apartment, is conveniently located approximately 3.9km from the Leon Centre, 4.2km from the Monumento a los Héroes de la Restauración, and 4.7km from the Santiago Apostol Cathedral.
This 90-square-metre flat offers one bedroom, two bathrooms, sleeps seven guests, and includes a swimming pool, parking, and a fully equipped kitchen; a kids' pool and on-site mini-market add to its family-friendly appeal.
Dom. Rep. Exclusive 2 Bed Apt. Evaristo Morales - Caribbean
9.7 52 reviews

Dom. Rep. Exclusive 2 Bed Apt. Evaristo Morales

apartment, Santo Domingo
This Santo Domingo apartment rental is situated in the Evaristo Morales district, a 1.6km walk from Blue Mall, 2.7km from Agora Mall, and 1.6km from the city centre, offering easy access to Santo Domingo's attractions.
The two-bedroom, three-bathroom flat features a fully equipped kitchen, free Wi-Fi, private parking, a terrace, and access to a fitness centre and garden; it comfortably accommodates families or groups of up to six.
Beautiful Centric Apt, Full Ac, Fast Wi-fi, Pool, Gym, Near All - Caribbean
10 1 review

Beautiful Centric Apt, Full Ac, Fast Wi-fi, Pool, Gym, Near All

apartment, Santo Domingo
This Santo Domingo City apartment boasts a prime downtown location, less than 2km from Plaza de la Cultura and the Malecon, offering easy access to the Eduardo Brito National Theatre and Basilica Catedral Nuestra Señora de la Altagracia.
The 65 square metre flat comprises two bedrooms, two bathrooms, accommodates four guests, and includes amenities such as a swimming pool, fitness centre, and free Wi-Fi.

Best Caribbean holiday rentals with parking

2br/2ba Beachfront Sunset Terrace  Parking - Caribbean
9.6 50 reviews

2br/2ba Beachfront Sunset Terrace Parking

apartment
This San Pedro de Macorís flat offers an unparalleled first-line beachfront position at Playa del Faro, providing direct access to beach bars and spectacular sunset views, with the Malecón and its fish restaurants just 500 metres away.
This two-bedroom, two-bathroom property accommodates up to six guests and features a private terrace and garden with sea views, air conditioning in both bedrooms, a well-equipped kitchen with granite countertops, fast WiFi, a Smart TV, and secure, complimentary on-site parking with 24/7 camera surveillance.
"Gorgeous And Open" 2 Bedroom / 2 Bath Villa - Caribbean
9.9 50 reviews

"Gorgeous And Open" 2 Bedroom / 2 Bath Villa

house, Bimini
This waterfront villa in Alice Town, Bimini, offers direct access to a private beach and is within walking distance of the casino, hotels, and restaurants.
The two-bedroom, two-bathroom property sleeps six guests and boasts a fully updated kitchen, smart home technology, multiple large smart TVs, keyless entry, and a swimming pool, all within easy reach of Bimini Bay Marina and Rainbow Reef.
Modern Apartment In The Heart Of Santo Domingo N&a - Caribbean
9.7 138 reviews

Modern Apartment In The Heart Of Santo Domingo N&a

apartment, Santo Domingo
This apartment is situated in Ciudad Universitaria, a lively district in Santo Domingo, within walking distance of the Palace of Fine Arts and the Malecon. The apartment has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The apartment offers two bedrooms, providing ample space for families or groups of friends. Guests can enjoy a range of amenities including a garden, a terrace, a fitness centre, a spa, and a fully equipped kitchen.
Weldon's Tropical Retreat | Casa Linda Villa - Caribbean
10 9 reviews

Weldon's Tropical Retreat | Casa Linda Villa

apartment
This two-bedroom villa is located within the exclusive Casa Linda Resort in Sosúa, Dominican Republic, a 5-minute drive from Sosúa and a 10-minute drive from Cabarete, with Puerto Plata Airport 20 minutes away. Guests can enjoy a private pool, a fully equipped kitchen, BBQ facilities, and access to resort amenities including a waterpark, playground, mini-golf, tennis/pickleball court, restaurant, and poolside bar, with a complimentary shuttle service to local beaches and towns.
©2026 cozycozy.com