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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

Ella Villa Negril Relaxing Peaceful Private Swimming Pool And 20min From Beach! - Caribbean
No reviews

Ella Villa Negril Relaxing Peaceful Private Swimming Pool And 20min From Beach!

cottage, Negril
Ella Villa apartment, located in Negril's West End district, is a 5-minute drive from Negril's town center, close to Seven Mile Beach and attractions like Barney's Botanical Garden and Kool Runnings Water Park.
This two-bedroom, one-bathroom rental sleeps five, offering a kitchen with a fridge and microwave, air conditioning, a swimming pool, parking, and Wi-Fi; enjoy a peaceful, private stay near Negril's beaches and nightlife.
Sea Life Apartamentos En Vía Principal Centro Y San Luis - Caribbean
9.2 200 reviews

Sea Life Apartamentos En Vía Principal Centro Y San Luis

apartment, San Andrés
This apartment in San Luis, San Andrés, is located just a short walk from public transportation and 2 kilometers from the airport, making it a convenient choice for travelers. It consistently receives excellent ratings for cleanliness and overall user experience, with a very good location rating.
The apartment features two bedrooms, a living room with a sofa bed, and a fully equipped kitchen. Amenities include air conditioning, a private terrace, a garden, and free Wi-Fi, as well as access to a private beach with water sports activities.
Captains Cottage Close To Beach! Minutes To Singer Island & Peanut Island! - Caribbean
9.6 5 reviews

Captains Cottage Close To Beach! Minutes To Singer Island & Peanut Island!

cottage, Riviera Beach
This Riviera Beach cottage, a five-minute walk from a kayak launch to Peanut Island and Blue Heron Bridge, offers easy access to West Palm Beach attractions and local amenities like Publix and a Tiki Bar.
The 1000-square-foot house features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, private backyard with BBQ, beach gear, and a private driveway suitable for boat parking.
Gated, Pool & Cabana, Near Beach, Modern,2br Condo - Caribbean
10 70 reviews

Gated, Pool & Cabana, Near Beach, Modern,2br Condo

apartment
This Cable Beach condo is centrally located in Nassau, minutes from Nassau International Airport, Bahamar Resort, and Sandport Beach.
This 1200-square-foot apartment features two bedrooms, two bathrooms, a fully equipped kitchen with a dishwasher, in-unit laundry, two smart TVs, and a covered patio; it comfortably sleeps four guests and offers access to an on-site pool and spa.

Best Caribbean lodging with a balcony

Cabins At Bonefish Bay - Caribbean
9.4 128 reviews

Cabins At Bonefish Bay

cabin, Marathon
This Marathon vacation rental is centrally located, a 10-minute walk from Coco Plum Beach, the Marathon Visitor Center, and San Pablo Catholic Church, with Sunset Park Beach and Curry Hammock State Park a short 15-minute drive away. This fully equipped cabin boasts a kitchen with a fridge, freezer, and microwave, air conditioning, a swimming pool, a terrace, a garden, parking, and on-site laundry facilities, plus free bicycle use for exploring the area.
Apartamento Frente Al Mar - Caribbean
9.0 46 reviews

Apartamento Frente Al Mar

apartment
This apartment is located in Bocagrande, a popular tourist district in Cartagena de Indias, just steps away from Bocagrande Beach and a short drive from Castillogrande Beach. The apartment has received excellent user ratings, with very good scores for location and cleanliness.
The apartment features two bedrooms and two bathrooms, offering ample space for a comfortable stay. Enjoy convenient amenities like air conditioning, a kitchen with a fridge and microwave, a private balcony, free parking, and access to a swimming pool, fitness center, spa, and garden.
Enjoy Huge 4 Bedrooms And 3 Bathrooms - Caribbean
No reviews

Enjoy Huge 4 Bedrooms And 3 Bathrooms

apartment, Santiago de los Caballeros
This four-bedroom, three-bathroom condo in Santiago de los Caballeros offers 1880 square feet of living space, accommodating up to seven guests with a fully equipped kitchen, air conditioning, and a private balcony. The property features convenient private parking and is situated in an open-space area with easy access to city attractions, perfect for exploring Santiago de los Caballeros.
Lovely One-bed Waterfront Apartment - Caribbean
9.8 109 reviews

Lovely One-bed Waterfront Apartment

apartment
This Freeport apartment is located just a 10-minute walk from the Lucayan Archipelago and Port Lucaya Marketplace, placing you in the heart of the action. Guests consistently rate the apartment excellent for location, cleanliness, and overall experience.
This one-bedroom rental offers 600 square feet of space, comfortably accommodating two guests. Enjoy amenities like a swimming pool, jacuzzi, garden, and a fully equipped kitchen, providing everything you need for a relaxing and enjoyable stay.

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

New Sunset Villa W/private Pool - Casa Linda - Caribbean
9.9 56 reviews

New Sunset Villa W/private Pool - Casa Linda

apartment
This modern two-bedroom villa, near Cabarete and Sosúa, Dominican Republic, is approximately 20 minutes from Puerto Plata International Airport (POP).
This luxury rental boasts a private pool with a bar, a full kitchen, smart TVs, Starlink internet, and sleeps four guests, offering resort-style amenities including access to a nearby waterpark and 24/7 gated security.
Wiggins Pass Chalet - Caribbean
9.5 898 reviews

Wiggins Pass Chalet

aparthotel, Naples Park
Wiggins Pass Chalet is located in Naples Park, just a short drive from Delnor-Wiggins Pass State Park and Silverspot Cinema. This 4-star aparthotel has received excellent user ratings for its location, cleanliness, and overall experience.
The apartment-style accommodations offer a comfortable and convenient stay with fully equipped kitchens, private bathrooms, and a terrace or balcony. Enjoy amenities such as a shared lounge, a garden, a restaurant, and free Wi-Fi and parking.
Espectaculares Aptos Hansa Coral San Andres Islas - Caribbean
9.0 180 reviews

Espectaculares Aptos Hansa Coral San Andres Islas

apartment, San Andrés
Espectaculares Aptos Hansa Coral San Andrés, a beachfront rental in San Andrés, is conveniently located 1.2 miles from Gustavo Rojas Pinilla International Airport, near Spratt Bight Beach, Los Almendros Beach, and San Andrés Bay.
This 750-square-foot (approximately 70 square meter) one-bedroom apartment sleeps up to 11 guests and features a fully equipped kitchen with microwave, air conditioning, a balcony, a swimming pool, free Wi-Fi, and parking; on-site amenities include a rooftop pool, kids' pool, and a mini-market.
1 Br King- Rooftop Pool Close To Beach Casa Costa - Caribbean
9.4 109 reviews

1 Br King- Rooftop Pool Close To Beach Casa Costa

apartment, Boynton Beach
This Boynton Beach condo is situated by the sea, within walking distance of Gulfstream Mall and Boynton Harbor Marina. Guests have rated this accommodation as excellent for its location, cleanliness, and overall experience.
The condo has 1 bedroom, 1 bathroom, and can accommodate up to 4 guests. It features a kitchen with full appliances, a washing machine, a sofa bed, and free WiFi. Guests can also enjoy a balcony, a water park, a fitness center, a sauna, concierge services, and valet parking.

Best Caribbean lodging with laundry available

Loblolly 2, Suite Vue Mer Sur La Plage, Piscine ! - Caribbean
10 54 reviews

Loblolly 2, Suite Vue Mer Sur La Plage, Piscine !

apartment
This 1-bedroom suite, offering direct beach access, is situated in the ALAMANDA residence on Orient Bay, within walking distance to shops and restaurants.
This studio apartment accommodates 2 guests and features a kitchen with a fridge, freezer, and microwave, plus air conditioning, a swimming pool, garden, and parking.
Beachfront Cap Cana Estate · Private Beach · Spa - Caribbean
No reviews

Beachfront Cap Cana Estate · Private Beach · Spa

apartment
Villa Guacamaya is an exclusive beachfront estate on Playa Juanillo within the prestigious gated community of Cap Cana, approximately 5 miles from Punta Cana International Airport.
This luxurious villa accommodates up to 18 guests with 9 bedrooms and 11 bathrooms, featuring a 200-foot swimming pool, a full-service spa, a private cinema, and a resident team including private chefs.
3br 2ba • Backup Power • Ac • Wifi • Gym • 24h Security • Ideal For Long Stays - Caribbean
No reviews

3br 2ba • Backup Power • Ac • Wifi • Gym • 24h Security • Ideal For Long Stays

apartment, Santiago de los Caballeros
This 1130 sq ft apartment in Santiago de los Caballeros, Dominican Republic, is located within the secure Garden Tower complex, offering 24/7 security, and is a short drive from Cibao International Airport and minutes from HOMS hospital. This family-friendly residence accommodates up to 6 guests with 3 bedrooms, 2 bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, and a secure balcony with protective mesh.
The Salty Cracker - Caribbean
10 123 reviews

The Salty Cracker

apartment, LaBelle
This secluded 14-acre hobby horse farm rental is located 2 miles from downtown LaBelle, offering a peaceful escape on a property with a quarter-mile driveway and roundabout.
This family-friendly cottage accommodates up to 4 guests and features air conditioning, a full kitchen, a swimming pool, hot tub, fitness center, and parking for boats and RVs, with optional swamp buggy tours and pontoon boat rentals available.
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