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371550 available short term rental offers

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Caribbean short term rentals
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Best Short term and Weekly rentals in Caribbean

Best family friendly Caribbean Short term rentals

Among the 371550 accommodations in Caribbean, here are the 4 best family friendly rentals

Apartamentos Sweet Island - Caribbean
8.8 103 reviews

Apartamentos Sweet Island

apartment, San Andrés
Apartamentos Sweet Island is located in San Andrés, close to popular beaches like Playa Decameron Marazul, Spratt Bight Beach, and North End, offering easy access to attractions like The Hill and San Luis. This apartment has received very good user ratings, good location ratings, and excellent cleanliness ratings.
The rental comes with a kitchen, a bathroom, air conditioning, and a terrace. You can enjoy amenities like bike rentals, on-site parking, and sightseeing tours, plus you can even rent a car to explore the island at your own pace.
Apartamento Turístico Familiar The Upper Room - Caribbean
9.4 55 reviews

Apartamento Turístico Familiar The Upper Room

apartment, San Andrés
Apartamento Turístico Familiar The Upper Room is conveniently located in San Andrés, a 6-minute walk from North End and less than a mile from Gustavo Rojas Pinilla International Airport, offering easy access to Spratt Bight Beach, Los Almendros Beach, and Parceras Beach.
This 220-square-foot family-friendly rental features one bedroom, one bathroom, a fully equipped kitchen, and a private terrace; it comfortably sleeps seven guests and includes amenities such as air conditioning, Wi-Fi, and a washing machine.
Beachfront Apartment, Quiet 4 Beds, 1 Bath, Ac, Wi-fi, Hot Water, In Paraiso Near Los Patos - Caribbean
9.3 168 reviews

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

apartment, Paraíso
This beachfront apartment rental in Paraíso, near Paraíso Beach and Los Patos, offers stunning sea and mountain views.
The 860-square-foot (approximately 80-square-meter) unit features three bedrooms, a living room, a full kitchen, one bathroom, a private terrace, and amenities including a swimming pool, parking, and free Wi-Fi; it also provides an indoor play area for children and airport transfer services.
Lakeside Miami *Superior Comfort* Airy 3/2 - Caribbean
9.9 88 reviews

Lakeside Miami *Superior Comfort* Airy 3/2

apartment, The Crossings
This waterfront vacation home is located in The Crossings, within 2 km of Kendall Breeze Shopping Center and 5 km of The Palms at Town & Country. It has excellent user, location, and cleanliness ratings.
The house has 3 bedrooms, 2 bathrooms, and a floor area of 1350 square feet. It comes with a fully equipped kitchen, free WiFi, air conditioning, a swimming pool, a terrace/balcony, a garden, a spa, and parking. Pets are allowed, and it's family-friendly.

Best Caribbean lodging with a balcony

Marina Bay - Caribbean
8.7 133 reviews

Marina Bay

apartment, Las Terrenas
This Las Terrenas beachfront rental, Marina Bay apartments, is steps from Las Ballenas Beach and a 7-minute walk from Pueblo de los Pescadores.
The one-bedroom, one-bathroom unit features a rooftop pool, fitness center, free Wi-Fi, and private parking, plus a shared kitchen and on-site mini-market.
Eco Hostal Kuima - Caribbean
9.3 387 reviews

Eco Hostal Kuima

B&B, El Zaino
Eco Hostal Kuima is a charming bed and breakfast located in El Zaino, just a short distance from the town center, beaches, and markets. The property consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The guest house features a peaceful garden setting with a private patio and barbecue facilities. Guests can enjoy amenities such as a shared kitchen, a swimming pool, a jacuzzi, and a terrace, along with convenient services like room service and a 24-hour front desk.
Remodeled H402 Beach Access Ocean View Penthouse - Caribbean
9.7 199 reviews

Remodeled H402 Beach Access Ocean View Penthouse

apartment
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.
Self Check In , Moderno, A/c Completo Wifi, Tv 4k - Caribbean
8.2 13 reviews

Self Check In , Moderno, A/c Completo Wifi, Tv 4k

apartment, Santiago de los Caballeros
This modern Santiago de los Caballeros apartment rental is conveniently located 1.3 miles from the Leon Center and within a short drive of the Monumento a los Héroes de la Restauración, La Aurora Cigar Factory, and Cibao Stadium.
This 1560-square-foot, three-bedroom, two-bathroom unit sleeps nine guests and features a fully equipped kitchen, private parking, a balcony, a garden, air conditioning, and 4K TV with Wi-Fi.

Frequently Asked Questions about short term rentals in Caribbean

  • What attractions should you visit during a week-long stay in the Caribbean?

    A week in the Caribbean is a great start! For a balanced trip, consider spending a few days exploring a major city like San Juan, Puerto Rico, with its historic forts (Castillo San Felipe del Morro and Castillo San Cristobal) and vibrant Old San Juan. Then, head to a beach destination like Barbados for relaxation and watersports. Seven Mile Beach in Negril, Jamaica, or Grace Bay Beach in Providenciales, Turks and Caicos, are also excellent choices depending on your budget. If you have time, a day trip to explore a rainforest or go snorkeling/diving is highly recommended.
  • What are the best short term rentals in Caribbean?

    Among the short term rentals in Caribbean, Folly Vacation Fantastic Vibe Incredible Apt D, Private Bungalow @ Bacalar 7 Colors Lagoon and Bay Harbor One Vacation are the most popular ones.

  • What attractions should you visit when you spend a month in the Caribbean?

    A month gives you time for island hopping! Start in Cuba, exploring Havana's colonial architecture and experiencing the unique culture. Then, fly to the Dominican Republic to visit Santo Domingo, a historical city, and enjoy some of the beautiful beaches. Next, consider Puerto Rico for its diverse landscape, from rainforests to beaches to historical sites. You could even squeeze in a visit to a smaller island like St. Lucia or Grenada for a more laid-back experience, focusing on hiking, exploring smaller towns, and enjoying the unique local cuisine.
  • What are the best short term rentals with a pool in Caribbean?

    Bay Harbor One Vacation, Righetto Vacation Rentals and Portofino Tower 3 Unit 1601 are the best short term rentals with a pool in Caribbean.

  • Can visitors to the Caribbean witness any unique natural cycles, like cherry blossom season or autumn colors?

    The Caribbean doesn't have the same seasonal changes as temperate regions. You won't find cherry blossoms or autumn foliage. However, you can experience the vibrant colors of tropical flowers blooming throughout the year, and you might see variations in the intensity of the green landscape depending on the rainfall.
  • What are the best short term rentals with a jacuzzi in Caribbean?

    The best short term rentals with a jacuzzi in Caribbean are Bay Harbor One Vacation, Portofino Tower 3 Unit 1601 and Paradise Beach Club - Oceanfront And Penthouse.

  • What are the most meaningful ways to engage with locals and discover the culture in the Caribbean?

    To truly experience Caribbean culture, visit local markets like the Mercado Modelo in Santo Domingo or the Bridgetown Market in Barbados. Attend local events or festivals. Take a cooking class focused on Caribbean cuisine, learning to prepare dishes like jerk chicken or mofongo. Consider staying in a locally owned guesthouse or 'casa particular' instead of a large resort. Speaking some basic Spanish or French Creole will help a lot, depending on which island you're on.
  • What are the best short term rentals for families and kids in Caribbean?

    The best short term rentals for families and kids in Caribbean are Folly Vacation Fantastic Vibe Incredible Apt D, Bay Harbor One Vacation and Righetto Vacation Rentals.

  • Are there any distinctive cultural activities or hands-on workshops in the Caribbean?

    Absolutely! Many islands offer rum distilling tours and workshops where you can learn about the process and sample different rums. Pottery classes showcasing traditional techniques are available in some locations. You can also find workshops focusing on local crafts like basket weaving or tie-dye. Many resorts and local organizations offer cooking classes focusing on Caribbean cuisine.
  • What are some secret spots or hidden treasures to visit in the Caribbean?

    This depends on which island you visit, but generally, exploring smaller, less-visited islands or towns within larger islands can reveal hidden gems. Look for secluded beaches accessible only by boat, explore less-touristy hiking trails in rainforests, and visit local fishing villages to see a different side of life. Specific examples are difficult to give without knowing your destination preference, as these 'hidden treasures' are by nature not widely publicized.
  • What should not be left out of your suitcase if you are going to the Caribbean?

    Pack light, breathable clothing suitable for warm weather. Don't forget swimwear, sunscreen (high SPF!), a hat, sunglasses, and insect repellent. Comfortable walking shoes are essential for exploring, and a reusable water bottle will help you stay hydrated. A small backpack is useful for day trips, and a universal travel adapter is necessary if you're bringing electronic devices. Consider a light rain jacket or poncho for unexpected showers.
  • What are the most popular festivals in the Caribbean?

    Carnival is a major event across many Caribbean islands, with vibrant parades, music, and dancing. Dates vary by island. Crop Over in Barbados is a huge celebration of the end of the sugarcane harvest. Junkanoo in the Bahamas is a street parade with elaborate costumes and music. These are just a few examples; many other local festivals take place throughout the year, celebrating various aspects of Caribbean culture.
  • Where should you try the best local food in the Caribbean?

    The best local food is often found in smaller, family-run restaurants and local eateries, away from the main tourist areas. Explore local markets and street food stalls for authentic flavors. Specific recommendations depend on the island, but look for dishes unique to the region. For example, try mofongo in Puerto Rico, jerk chicken in Jamaica, or conch fritters in the Bahamas. Don't be afraid to venture off the beaten path to find culinary gems.

Best Caribbean lodging with a kitchen

Oceanview Lighthouse Villa - Caribbean
9.3 71 reviews

Oceanview Lighthouse Villa

apartment, Maunabo
This Maunabo apartment is conveniently located just a 10-minute walk from Maunabo Beach and a 47-mile drive from Luis Muñoz Marín International Airport. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The 1300 square foot apartment comfortably accommodates up to 8 guests in its 3 bedrooms. Enjoy access to a private beach, a swimming pool, a hot tub, a tennis court, and a garden, as well as amenities like a fully equipped kitchen, a terrace, and complimentary Wi-Fi.
Heated Pool & Spa  Waterfront  Near Tigertail - Caribbean
No reviews

Heated Pool & Spa Waterfront Near Tigertail

apartment, Marco Island
This Marco Island condo offers waterfront canal views and is located minutes from Tigertail Beach, restaurants, shops, and golf.
This 3-bedroom, 3-bathroom residence accommodates up to 7 guests, featuring a private heated pool and spa, complimentary bikes, and included beach gear for a complete island experience.
Apartamentos Hansa Reef - Mejor Ubicación. - Caribbean
9.6 17 reviews

Apartamentos Hansa Reef - Mejor Ubicación.

apartment, San Andrés
Apartamentos Hansa Reef is a family-friendly apartment located in San Andrés, just steps away from Spratt Bight Beach and a short walk from Los Almendros Beach. It has excellent ratings for its location, cleanliness, and user experience.
The apartment features a fully equipped kitchen with a fridge and microwave oven, air conditioning, a private balcony or terrace, and access to a shared swimming pool and garden. It also offers free Wi-Fi, a flat-screen TV, and a coffee machine for added convenience.
The Bricks: Rooftop Pool With Ocean & City Views. - Caribbean
9.7 214 reviews

The Bricks: Rooftop Pool With Ocean & City Views.

apartment
This apartment in Downtown Santo Domingo is conveniently located within a 2 km radius of major shopping malls, historical landmarks, and cultural attractions. It has earned excellent ratings for its cleanliness, location, and overall guest experience.
This 2-bedroom, 2-bathroom unit can accommodate up to 6 guests. You'll enjoy a fully equipped kitchen, a washing machine, free Wi-Fi, a smart TV, and access to a swimming pool, fitness center, and barbecue grills.

Best Caribbean lodging with laundry available

The Hills Residence - Caribbean
8.3 578 reviews

The Hills Residence

aparthotel, Simpson Bay
The Hills Residence is an aparthotel located in Simpson Bay, 1.2 miles from Princess Juliana International Airport and a 7-minute walk from Kim Sha Beach.
This family-friendly aparthotel offers air-conditioned rooms with kitchens, a swimming pool, a hot tub, on-site dining, and a casino.
Complejo Ecoturistico Rancho Cielo - Caribbean
8.6 70 reviews

Complejo Ecoturistico Rancho Cielo

B&B, Licey al Medio
Complejo Ecoturistico Rancho Cielo is a family-friendly bed and breakfast located in Licey al Medio, a short drive from attractions like Kaskada Park, La Aurora Cigar Factory, and Leon Center.
This 60-square-foot guest house features one bedroom, one bathroom, and can accommodate up to three guests, offering a fully equipped kitchen, air conditioning, a terrace, and a garden.
Beach Style Cottage - Caribbean
9.2 10 reviews

Beach Style Cottage

cottage, La Romana
This La Romana cottage is located just a short distance from Playa Caleta, making it ideal for beach lovers. The cottage is also close to Playa de la Isla Catalina and El Obelisco, offering easy access to other popular attractions. The cottage has consistently received excellent ratings from previous guests.
This vacation rental sleeps up to six guests in three bedrooms and two bathrooms. The cottage features a private pool, a fully equipped kitchen, a washing machine, air conditioning, and a terrace.
Walk To Best Eats And Shops And Stay In Style - Caribbean
9.9 15 reviews

Walk To Best Eats And Shops And Stay In Style

apartment, Fort Myers
Cracker Cow Cottages - Cottage A, a recently renovated apartment in Fort Myers, is conveniently located near Southwest Florida International Airport (14 miles), Fisherman's Village (24 miles), and the Sanibel and Captiva Islands Chamber of Commerce and Visitors Center (18 miles).
This 400-square-foot unit features one bedroom, one bathroom, a fully equipped kitchen, and accommodates two guests, offering amenities such as a private patio with river views, a garden, a spa, a tennis court, free Wi-Fi, and free parking.
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