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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

Haynes Cay View - Caribbean
9.3 161 reviews
Caribbean
06/20 – 06/27
$70/nighttotal: $490 (7 )

Haynes Cay View

1 2
apartment , San Andrés
Haynes Cay View apartments are located near Rocky Cay Beach in San Andrés, Colombia, a 10-minute walk from the beach and a 15-minute drive from San Andrés City Center and the airport.
These pet-friendly, family-friendly units offer one bedroom, a kitchenette with a fridge and microwave, air conditioning, a terrace, and free WiFi, plus a welcome package including wine, breakfast supplies, and coffee; nearby activities include snorkeling and boat trips arranged through the on-site tour desk.
Lovely Penthouse With Incredible View - Caribbean
9.2 74 reviews
Caribbean
10/19 – 10/23
$335/nighttotal: $1340 (4 )

Lovely Penthouse With Incredible View

3 8
apartment , San Andrés
This three-bedroom, three-bathroom penthouse apartment is located near Spratt Bight Beach in San Andrés, Colombia, a short walk from Los Almendros Beach and about a mile from San Andrés Bay, offering easy access to North End and Gustavo Rojas Pinilla International Airport.
The 1350-square-foot unit features a fully equipped kitchen, private entrance, free Wi-Fi, access to a swimming pool, terrace, and garden, comfortably accommodating families or groups with stunning views.
Beautiful Condo With A Tree House Feel - Caribbean
9.5 97 reviews
Caribbean
12/19 – 12/26
$169/nighttotal: $1183 (7 )

Beautiful Condo With A Tree House Feel

1 4
apartment , Port St. Lucie
This apartment is located in Port Saint Lucie, within 1 mile of PGA Village and 3 miles of Superplay USA and Clover Park. It has excellent user, location, and cleanliness ratings.
This one-bedroom, one-bathroom apartment accommodates up to four guests and features a fully equipped kitchen, a washing machine, free WiFi, and a balcony. The smoke-free condo building offers an outdoor pool and is pet-friendly.
Cozy Studio | Wifi | Terrace -3 Min From The Beach - Caribbean
9.8 133 reviews
Caribbean
08/24 – 08/31
$54/nighttotal: $378 (7 )

Cozy Studio | Wifi | Terrace -3 Min From The Beach

1 2
house , Varadero
Casa Omar & Anabel is a private studio located just steps from the famous Varadero beach, offering easy access to the white sand and turquoise waters. The studio has received excellent ratings for cleanliness, location, and overall user experience.
The studio features a spacious layout with 270 square feet, accommodating up to 3 guests. It offers a private bathroom, a comfortable bed, a terrace with loungers, and a range of amenities including air conditioning, a television, and a pantry.

Best Caribbean lodging with a balcony

Upscale 1br, Near Blue Mall | Rooftop| Yellowkey - Caribbean
9.6 141 reviews
Caribbean
11/09 – 11/16
$101/nighttotal: $707 (7 )

Upscale 1br, Near Blue Mall | Rooftop| Yellowkey

1 2
apartment , Santo Domingo
This apartment is located in Downtown Santo Domingo, within walking distance of shopping malls, entertainment venues, and the historic Gate of San Diego. It has excellent ratings for location, cleanliness, and user experience.
This one-bedroom rental can comfortably accommodate two guests. You'll have access to a fully equipped kitchen, a balcony, a fitness center, and parking, making it easy to explore the city and enjoy a comfortable stay.
Paradise Found/breathtaking Views /With Dedicated Wifi - Caribbean
9.6 82 reviews
Caribbean
06/26 – 06/30
$309/nighttotal: $1236 (4 )

Paradise Found/breathtaking Views /With Dedicated Wifi

1 4
apartment , St Thomas
This Red Hook condo is a short walk from Sapphire Beach and a five-minute drive from Red Hook's ferry terminal, offering easy access to St. John and the British Virgin Islands.
The 790-square-foot unit features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, two TVs, Wi-Fi, a terrace, and access to two swimming pools, beach chairs, and snorkeling gear.
Beachfront Apartment, Quiet 4 Beds, 1 Bath, Ac, Wi-fi, Hot Water, In Paraiso Near Los Patos - Caribbean
9.2 165 reviews
Caribbean
07/15 – 07/18
$106/nighttotal: $318 (3 )

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

3 2
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.
Oceanview Lighthouse Villa - Caribbean
9.1 70 reviews
Caribbean
08/24 – 08/31
$173/nighttotal: $1211 (7 )

Oceanview Lighthouse Villa

3 2
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.

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

Amazing View In Aventura! Cozy 2 Bd At The Yacht Club - Caribbean
9.7 55 reviews
Caribbean
12/19 – 12/26
$459/nighttotal: $3213 (7 )

Amazing View In Aventura! Cozy 2 Bd At The Yacht Club

2 4
apartment , Aventura
This 2-bedroom, 2-bathroom apartment is located in Aventura, within a 5km radius of Aventura Mall, Aventura Hospital & Medical Center, and Gulfstream Park Racing and Casino, offering easy access to shopping, entertainment, and healthcare. This rental receives excellent ratings for location, cleanliness, and overall user experience.
The apartment comfortably accommodates 6 guests and features a fully equipped kitchen, a private pool, and a fenced-in yard. Enjoy the amenities of the building, including an indoor pool, barbecue grills, a fitness center, and a terrace, all while taking advantage of the free WiFi and enjoying the smoke-free environment.
619 Beach Daze | Mins To Beaches Shopping & Dining - Caribbean
9.8 171 reviews
Caribbean
07/11 – 07/18
$230/nighttotal: $1610 (7 )

619 Beach Daze | Mins To Beaches Shopping & Dining

3 6
apartment , Naples Park
This Naples Park vacation home boasts three bedrooms and two bathrooms, sleeping six, and is less than 1.2 miles from Vanderbilt Beach, Mercato shopping center, and Pelican Bay Community Park.
The property features a private balcony, swimming pool, tennis court, fully equipped kitchen, free WiFi, and barbecue grills, plus easy beach access and an on-site water park.
Superbe Studio Dolce Vita Vue Mer Plage Piscine - Caribbean
8.9 129 reviews
Caribbean
08/24 – 08/31
$97/nighttotal: $679 (7 )

Superbe Studio Dolce Vita Vue Mer Plage Piscine

1 2
studio , Marigot
This beachfront studio apartment in Marigot, near Nettle Bay Beach and a 17-minute walk from Baie de la Potence Beach, offers convenient access to popular Marigot attractions.
The 320-square-foot (approximately 30-square-meter) unit features a bedroom, living room, fully equipped kitchen with fridge and microwave, private balcony with sea views, and access to a swimming pool and free Wi-Fi; it sleeps up to two guests.
Apartamento Frente Al Mar - Caribbean
9.3 85 reviews
Caribbean
11/09 – 11/16
$62/nighttotal: $434 (7 )

Apartamento Frente Al Mar

1 2
apartment , San Felipe de Puerto Plata
Apartamento Frente Al Mar is a beachfront apartment in San Felipe de Puerto Plata, just steps from El Chaparral beach and a short drive from Dorada beach. This rental has excellent ratings for location, cleanliness, and overall user experience.
The one-bedroom apartment features a kitchen with a fridge and microwave, air conditioning, and a private balcony. Enjoy the on-site amenities like the swimming pool, spa, fitness center, and restaurant, or take advantage of the airport shuttle service, car rental, and other conveniences.

Best Caribbean lodging with laundry available

Modern Beach Condo At Peaceful Hutchinson Island - Caribbean
9.8 155 reviews
Caribbean
12/19 – 12/26
$180/nighttotal: $1260 (7 )

Modern Beach Condo At Peaceful Hutchinson Island

1 4
apartment , Fort Pierce
This one-bedroom, one-bathroom apartment is located in a beachside community in Fort Pierce, offering direct access to the beach and easy access to the city's attractions. The apartment features a fully equipped kitchen, a washer and dryer, a pull-out couch, and access to a swimming pool, jacuzzi, tennis court, and fitness center.
Charming  Lovely View  Beach  Pool 702 - Caribbean
9.7 164 reviews
Caribbean
07/11 – 07/18
$173/nighttotal: $1211 (7 )

Charming Lovely View Beach Pool 702

2 6
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.
Bhserene Penthouse Oasis. Beach Steps Away, Pool, & Tranquility - Caribbean
9.8 81 reviews
Caribbean
10/19 – 10/23
$327/nighttotal: $1308 (4 )

Bhserene Penthouse Oasis. Beach Steps Away, Pool, & Tranquility

3 8
apartment , Humacao
This Humacao apartment is located in Palmas del Mar, just a short walk from the beach and a short drive from the Palmas Del Mar Golf Club, making it a great choice for travelers seeking both relaxation and recreation. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers 1,880 square feet of space, with three bedrooms and three bathrooms, comfortably accommodating up to eight guests. Enjoy access to a private pool, tennis courts, a fully equipped kitchen, and free Wi-Fi, along with a garden and parking.
"La Casa Delmar" Heated Pool! Close To Beaches And 5th Ave. - Caribbean
9.7 144 reviews
Caribbean
10/19 – 10/23
$340/nighttotal: $1360 (4 )

"La Casa Delmar" Heated Pool! Close To Beaches And 5th Ave.

4 8
apartment , Naples
This vacation home is located in East Naples, just a short walk from Village Plaza Shopping Center and Fifth Avenue South, offering easy access to shopping, dining, and entertainment. The property has received excellent ratings for cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
This 4-bedroom home comfortably accommodates up to 10 guests, providing ample space for families or groups of friends. Enjoy a refreshing dip in the private pool, relax in the fenced yard, prepare meals in the modern kitchen, and stay connected with free Wi-Fi, all while enjoying the Florida sunshine.
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