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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 253063 accommodations in Caribbean, here are the 4 best family friendly rentals

Amazing 2br 2ba Newly Reno Beachfront Apt W/beach View - Caribbean
9.0 177 reviews
Caribbean
11/01 – 11/15
$372/nighttotal: $5208 (14 )

Amazing 2br 2ba Newly Reno Beachfront Apt W/beach View

2 6
apartment , Hollywood
This beachfront apartment is located on Hollywood Beach, just steps from the sand and a short walk from North City Beach Park, offering easy access to the lively Hollywood Beach Boardwalk. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This two-bedroom, two-bathroom unit spans 1000 square feet, offering ample space for families and groups. Enjoy access to a swimming pool with ocean views, a fitness center, a terrace, a garden, and free parking, making it the perfect place to relax and explore Hollywood.
Santiago Comfort Suite - Caribbean
9.1 163 reviews
Caribbean
12/21 – 12/31
$38/nighttotal: $380 (10 )

Santiago Comfort Suite

3 3
studio , Santiago de los Caballeros
Aparta estudio en Santiago #1 offers a convenient Santiago de los Caballeros location, approximately 2.2 miles from Kaskada Park and 2.8 miles from both the San Luis Fortress and the Santiago Apostol Cathedral.
This recently renovated studio apartment features a fully equipped kitchen, air conditioning, a private bathroom, and a terrace, perfect for a comfortable stay for up to two guests.
Romantic Oceanfront Beach Bungalow On Beach Private W Club Resort Access &Tennis - Caribbean
10 11 reviews
Caribbean
08/27 – 09/05
$805/nighttotal: $7245 (9 )

Romantic Oceanfront Beach Bungalow On Beach Private W Club Resort Access &Tennis

1 2
cottage , south East Peninsula
This beachfront cottage in Basseterre, St. Kitts, offers the "Oceanfront Beach Bungalow On Beach, Private With Club Resort Access & Tennis" and is within three miles of multiple beaches including Sandy Bank, Banana Bay, Major's Bay, Lion's Beach, and Turtle Beach.
The 1600-square-foot bungalow features one bedroom, two bathrooms, sleeps three guests, and includes a private pool, free WiFi, a kitchenette, a washing machine, an outdoor patio, and a smart TV, along with resort amenities such as a swimming pool, spa, tennis court, and concierge service.
Ocean View Apartment In Rodadero Santa Marta - Caribbean
9.8 60 reviews
Caribbean
01/10 – 03/13
$96/nighttotal: $5952 (62 )

Ocean View Apartment In Rodadero Santa Marta

1 2
apartment , Gaira
This beachfront apartment in Gaira offers unparalleled 180-degree sea views of The Bay and Playa El Rodadero, featuring direct, private access to El Rodadero beach.
This fully renovated unit sleeps four guests and includes two bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, Wi-Fi, and access to a communal swimming pool, all within a building providing 24-hour security and parking.

Best Caribbean lodging with a balcony

2 Room Apartment, Pool, Balcony, Bbq, Kitchen - Caribbean
9.7 64 reviews
Caribbean
12/21 – 12/31
$68/nighttotal: $680 (10 )

2 Room Apartment, Pool, Balcony, Bbq, Kitchen

1 3
apartment , Boca Chica
This two-bedroom Boca Chica apartment rental is located 400 meters from Boca Chica Beach, a five-minute walk from restaurants and shops, and a 14-minute drive from Las Américas International Airport.
This 780-square-foot condo offers a fully equipped kitchen, one bathroom, sleeps six guests, and includes access to a swimming pool, fitness center, and parking.
Casa Kamanda, Zona Colonial, Santo Domingo - Caribbean
9.0 130 reviews
Caribbean
10/12 – 10/18
$41/nighttotal: $246 (6 )

Casa Kamanda, Zona Colonial, Santo Domingo

1 2
apartment , Santo Domingo
Casa Kamanda, a pet-friendly apartment rental in Santo Domingo's Zona Colonial, offers easy access to Montesinos Palace, Guibia Beach, and Puerto Santo Domingo, all within walking distance or a short taxi ride, and is 12 miles from Las Américas International Airport.
This family-friendly rental features a private patio, garden access, free Wi-Fi, air conditioning, a well-equipped kitchen (in select units), flat-screen TVs with streaming services, and a private bathroom with walk-in shower; check-out is between 8 AM and 12 PM.
Sarah's Place San Andres - Caribbean
8.8 115 reviews
Caribbean
06/23 – 07/01
$73/nighttotal: $584 (8 )

Sarah's Place San Andres

1 4
B&B , San Andrés
Sarah's Place San Andrés is located in San Andrés, a short distance from San Andres Bay, offering easy access to the island's main attractions. The guest house is rated very good for location, cleanliness, and overall experience.
The guest house features one bedroom and one bathroom, offering a blend of history and modern comfort. Enjoy amenities like free Wi-Fi, a shuttle service, bicycle rentals, a terrace with outdoor furniture, a safety deposit box, and convenient parking.
El Conde Del Macao - Caribbean
9.5 34 reviews
Caribbean
06/27 – 07/04
$53/nighttotal: $371 (7 )

El Conde Del Macao

2 2
apartment , El Macao
This vacation home is situated in Higuey, La Altagracia Province, 4.5 miles from Macao Beach and within 12 miles of Sirenis Aquagames Water Park and Punta Blanca Golf Course. It has excellent user and location ratings, and a cleanliness rating of excellent.
The house has a floor area of 650 square feet, 1 bathroom, and a private pool. It has a kitchen with a refrigerator and microwave, a washing machine, a balcony, a flat-screen TV, free WiFi in public areas, barbecue grills, and a garden. It also has a concierge and parking.

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

Charming  Lovely View  Beach  Pool 702 - Caribbean
9.7 164 reviews
Caribbean
07/30 – 08/03
$192/nighttotal: $768 (4 )

Charming Lovely View Beach Pool 702

2 2
apartment , Cartagena
This beachfront Cartagena apartment rental in the El Laguito neighborhood is a 10-minute walk from Castillo Grande and Bocagrande Beaches, and a 15-minute walk from El Laguito Beach and Centro Comercial Nao shopping center.
The 910-square-foot (85-square-meter) condo features two bedrooms, two bathrooms, a sofa bed for seven guests, a fully equipped kitchen, and amenities including a swimming pool, hot tub, fitness center, and private balcony with potential ocean views.
Chic Fully Serviced Apartment At Regatta Living Ii - 705 - Caribbean
9.5 107 reviews
Caribbean
08/20 – 08/24
$96/nighttotal: $384 (4 )

Chic Fully Serviced Apartment At Regatta Living Ii - 705

1 3
apartment , Los Prados
This one-bedroom apartment is conveniently located in Los Prados, just a short walk from the Blue Mall and a short drive from the Agora Mall. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features a private balcony and a fully equipped kitchen with a dishwasher and coffee machine. Guests can enjoy a range of amenities including air conditioning, a swimming pool, a jacuzzi, a fitness center, and free parking.
Across From The Beach Edificio El Nuevo Conquistador Apto 612 Barrio El Laguito - Caribbean
8.7 76 reviews
Caribbean
07/01 – 07/08
$63/nighttotal: $441 (7 )

Across From The Beach Edificio El Nuevo Conquistador Apto 612 Barrio El Laguito

1 2
apartment , Cartagena
This aparthotel in Cartagena is located in El Laguito, a quiet residential area just a short walk from Castillo Grande and Bocagrande Beaches. It is a 3-star property with very good user ratings for cleanliness and overall experience.
The apartment features a balcony and a fully equipped kitchen. Amenities include a swimming pool, parking, internet access, and a restaurant, providing a comfortable and convenient stay.
Amazing 2 Bedroom Beach Apartment For 6 (1 Of 2) - Caribbean
9.6 195 reviews
Caribbean
08/17 – 08/23
$108/nighttotal: $648 (6 )

Amazing 2 Bedroom Beach Apartment For 6 (1 Of 2)

2 4
apartment , Juan Dolio
This Juan Dolio condo rental in Villas Del Mar is conveniently located 0.4 miles from Marbella Beach and 2.3 miles from Los Marlins Golf Course, offering easy access to area attractions. This two-bedroom, two-bathroom vacation rental sleeps six guests and boasts a fully equipped kitchen, private fenced yard, access to a swimming pool, Jacuzzi, fitness center, and free Wi-Fi.

Best Caribbean lodging with laundry available

Casa Blanca Samaná - Las Galeras - Caribbean
9.4 398 reviews
Caribbean
08/08 – 08/18
$68/nighttotal: $680 (10 )

Casa Blanca Samaná - Las Galeras

1 3
apartment , Las Galeras
This apartment is conveniently located near several beautiful beaches in Las Galeras, including Playa Grande, La Playita Beach, and Colorado Beach, offering easy access to swimming, sunbathing, and water activities. It has received excellent ratings for user experience, location, and cleanliness.
This rental offers two bedrooms, providing ample space for families or groups of friends. The apartment boasts a range of amenities, including a swimming pool, jacuzzi, terrace, garden, and free Wi-Fi, making it a perfect choice for a relaxing and enjoyable vacation.
One Mile From Bonita Beach And Barefoot Beach! - Caribbean
9.9 122 reviews
Caribbean
08/17 – 08/23
$197/nighttotal: $1182 (6 )

One Mile From Bonita Beach And Barefoot Beach!

3 6
apartment , Bonita Springs
This Bonita Springs apartment is located in a quiet neighborhood, just a mile from Bonita Beach and Barefoot Beach, and four miles from Wiggins Beach. It has earned excellent ratings for location, cleanliness, and overall experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating six guests. It features a private heated pool with an enclosure and lanai area, beach towels and chairs, and a kitchen equipped with a fridge, microwave, and dishwasher.
Orient Bay Studio Saba Face à La Mer - Caribbean
8.7 68 reviews
Caribbean
11/20 – 11/30
$127/nighttotal: $1270 (10 )

Orient Bay Studio Saba Face à La Mer

1 4
studio , Cul de Sac
Orient Bay Studio SABA is a beachfront apartment located directly on Orient Bay Beach in Saint Martin, 1.2 miles from Grand Case Airport.
This 520-square-foot (48-square-meter) unit features one bedroom, one bathroom, a kitchenette with a fridge, freezer, microwave, and oven, plus free Wi-Fi, a terrace, and access to a shared pool; it sleeps up to two guests and includes free parking.
Cs7- Immaculate Colonial Studio In The Heart Of Santurce Centrally Located - Caribbean
9.5 782 reviews
Caribbean
06/27 – 07/04
$122/nighttotal: $854 (7 )

Cs7- Immaculate Colonial Studio In The Heart Of Santurce Centrally Located

1 4
studio , San Juan
This Santurce apartment rental is located less than a mile from the Museum of Contemporary Art of Puerto Rico and the José Miguel Agrelot Coliseum, and within 3 miles of Condado Beach and the Puerto Rico Convention Center.
The two-bedroom unit features a fully equipped kitchen, private patio, free Wi-Fi, and a Jacuzzi, comfortably accommodating families or groups; nearby attractions include public transportation access to Sacred Station (7-minute walk) and Hato Rey Station (17-minute walk).
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