Caribbean Short term rentals

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

Exclusivos Apartamentos Con Playa Privada - Caribbean
9.4 279 reviews
Caribbean
30/07 – 03/08
£171/nighttotal: £684 (4 )

Exclusivos Apartamentos Con Playa Privada

2 2
apartment , San Andrés
This apartment is located just 1.2 miles from Gustavo Rojas Pinilla International Airport and within easy reach of popular beaches like Spratt Bight Beach and Los Almendros Beach, making it a convenient and desirable base for exploring the island. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment spans 115 square metres and is perfect for families, offering spacious rooms and a range of amenities including a swimming pool, jacuzzi, sauna, and tennis court. Guests can also enjoy a private beach area, stunning lake views, and a fully equipped kitchen.
Unique Clean Private Pet Friendly House Close To Beaches And Wilton Manors - Caribbean
9.6 158 reviews
Caribbean
27/06 – 04/07
£156/nighttotal: £1092 (7 )

Unique Clean Private Pet Friendly House Close To Beaches And Wilton Manors

2 4
apartment , Oakland Park
This holiday home is located near the sea in Oakland Park, just under 5km from Funky Buddha Brewery, DRV PNK Stadium, and Wilton Drive. It has received excellent ratings for location, cleanliness, and overall experience.
The two-bedroom property spans 107 square metres and includes a private fenced yard, a terrace, and a fully equipped kitchen. Amenities include free Wi-Fi, air conditioning, and a barbecue grill, making it ideal for a relaxing and comfortable stay.
Wiggins Pass Chalet - Caribbean
9.4 878 reviews
Caribbean
08/07 – 20/07
£364/nighttotal: £4368 (12 )

Wiggins Pass Chalet

3 8
aparthotel , Naples Park
Wiggins Pass Chalet is a 4-star aparthotel in Naples Park, just 5.1 kilometres from Delnor-Wiggins Pass State Park and 17.7 kilometres from Tin City, offering a convenient base for exploring the area. It boasts excellent user ratings for location, cleanliness and overall experience.
Each self-catering apartment comes with a living area, a flat-screen TV, a well-equipped kitchen and a private bathroom. Guests can enjoy a terrace or balcony, a shared lounge area, a garden and a restaurant, as well as free Wi-Fi and parking.
Bayfront Budget Friendly 2 Bedrooms And 2 Bathrooms Apt In Gated Community - Caribbean
9.5 67 reviews
Caribbean
20/08 – 24/08
£94/nighttotal: £376 (4 )

Bayfront Budget Friendly 2 Bedrooms And 2 Bathrooms Apt In Gated Community

2 3
apartment , Portmore
This Portmore apartment, situated 3.2km from Sovereign Village Mall and within 14.5km of beaches such as Fort Clarence Beach and Hellshire Beach, offers convenient access to shopping and coastal attractions.
The two-bedroom, two-bathroom self-catering flat sleeps four guests and includes a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, garden, parking, free Wi-Fi, and in-unit laundry facilities.

Best Caribbean short term rentals with a balcony

Modern King Size Bed Condo With Pool By Agora Mall - Caribbean
9.6 201 reviews
Caribbean
28/12 – 09/01
£88/nighttotal: £1056 (12 )

Modern King Size Bed Condo With Pool By Agora Mall

1 3
apartment , Santo Domingo
This apartment is located in the heart of Downtown Santo Domingo, just a short walk from the Agora Mall and Blue Mall, placing you within easy reach of the city's vibrant shopping and cultural attractions. The apartment boasts excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The apartment offers one bedroom and can accommodate up to four guests, making it ideal for families or groups of friends. Guests can enjoy a range of amenities including a swimming pool, fitness centre, and a fully equipped kitchen, as well as the convenience of free Wi-Fi and a balcony.
Connect With Nature At Headwaters Retreat In Jupiter Farms - Caribbean
8.0 11 reviews
Caribbean
27/08 – 05/09
£206/nighttotal: £1854 (9 )

Connect With Nature At Headwaters Retreat In Jupiter Farms

4 2
cottage , Jupiter
This Jupiter Farms holiday home is situated 1.9km from Loxahatchee River Battlefield Park and 2.9km from Riverbend Park, offering easy access to other local nature reserves.
Sleeping eight guests in four bedrooms and two bathrooms, this self-catering property boasts a terrace, garden, free Wi-Fi, air conditioning, and parking, plus a fireplace and charcoal grills for outdoor entertaining.
Amazing 2br 2ba Newly Reno Beachfront Apt W/beach View - Caribbean
9.0 177 reviews
Caribbean
01/11 – 15/11
£277/nighttotal: £3878 (14 )

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

2 6
apartment , Hollywood
This beachfront flat is located on Hollywood Beach, just a short walk from North City Beach Park and close to other attractions. It has excellent ratings for location, cleanliness, and user experience.
The property offers two bedrooms and two bathrooms across 93 square metres. Amenities include a swimming pool, fitness centre, and a terrace, perfect for enjoying the sunny Hollywood weather.
Maritime Suite 2bd/2ba South Beach Villa Monaco - Caribbean
9.7 179 reviews
Caribbean
17/08 – 23/08
£174/nighttotal: £1044 (6 )

Maritime Suite 2bd/2ba South Beach Villa Monaco

2 4
apartment , Miami Beach
This South Beach apartment, near Biscayne Bay and a 2.4km stroll from Lincoln Road Mall, offers easy access to Miami Beach's attractions.
This spacious 186 sq m (2000 sq ft) duplex flat sleeps up to 10 guests in four king-size beds and two sofa beds, boasting four bathrooms, fully equipped kitchens, high-speed internet, and access to a swimming pool, garden, and parking.

Frequently asked questions about short term rentals in Caribbean

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

    A week in the Caribbean barely scratches the surface! Prioritise based on your interests. For beaches, consider Grace Bay Beach in Turks and Caicos or Seven Mile Beach in Grand Cayman. For history buffs, Old San Juan in Puerto Rico, or the historical sites in Havana, Cuba are essential. Nature lovers might explore the rainforest in Dominica or the lush landscapes of St. Lucia's Pitons. If you're into water sports, Barbados offers excellent surfing, while the Bahamas are ideal for diving and snorkelling.
  • What are the best short term rentals in Caribbean?

  • What attractions should one visit when spending a month in the Caribbean?

    A month allows for a deeper exploration! You could island hop, perhaps starting in Jamaica exploring Dunn's River Falls and Blue Mountains National Park, then moving to the Dominican Republic for a cultural experience in Santo Domingo and some time relaxing in Punta Cana. Consider exploring the lesser-known islands like Antigua and Barbuda, known for their stunning beaches and laid-back atmosphere, and finally, end your trip in Cuba, experiencing its vibrant culture and history in Havana and perhaps exploring the beaches of Varadero.
  • What are the best short term rentals with a pool in Caribbean?

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

    Visit local markets like the one in Bridgetown, Barbados, or the Mercado Modelo in Santo Domingo, Dominican Republic. Take a cooking class to learn about Caribbean cuisine, perhaps focusing on jerk chicken in Jamaica or mofongo in Puerto Rico. Attend local festivals and events – a great way to experience the vibrant culture. Consider staying in smaller guesthouses or homestays rather than large resorts for more authentic interactions.
  • What are the best short term rentals with a jacuzzi in Caribbean?

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

    Absolutely! Many islands offer rum distilling tours (Mount Gay Rum in Barbados is a popular choice), pottery classes showcasing local techniques, and workshops on traditional crafts like basket weaving or tie-dye. Music workshops focusing on reggae in Jamaica or calypso in Trinidad and Tobago are also readily available.
  • What are the best short term rentals for families and kids in Caribbean?

  • What are some secret spots or hidden treasures to visit in the Caribbean?

    This depends on your definition of 'secret'! Some lesser-known gems include the secluded beaches of Culebra, Puerto Rico; the untouched beauty of Virgin Gorda's Baths in the British Virgin Islands; or exploring the less-touristy areas of Dominica's rainforest. These require more research and potentially more effort to reach, but offer a more authentic experience.
  • What should not be left out of your suitcase if you are going to the Caribbean?

    Lightweight, breathable clothing is essential, along with swimwear and comfortable walking shoes. Sunscreen with a high SPF is crucial, as is insect repellent. A wide-brimmed hat and sunglasses will also protect you from the strong Caribbean sun. Don't forget a reusable water bottle to stay hydrated.
  • What are the most popular festivals in the Caribbean?

    Carnival celebrations are huge across many islands, with Trinidad and Tobago's Carnival being particularly famous. Jamaica's Reggae Sumfest is a major music festival. Other significant events include Crop Over in Barbados and Junkanoo in the Bahamas.
  • Where should one try the best local food in the Caribbean?

    The best local food is often found in smaller, family-run restaurants rather than large tourist establishments. Explore local markets and street food stalls for authentic flavours. In Jamaica, try a roadside jerk chicken stand; in Cuba, explore paladares (private restaurants); and in Puerto Rico, sample mofongo from a local eatery. Each island offers its own unique culinary delights.

Best Caribbean short term rentals with a kitchen

Cozy 1 Bedroom Unit Located In A Condo/hotel In The Heart Of Coconut Grove-free Parking - Caribbean
9.8 51 reviews
Caribbean
17/08 – 23/08
£149/nighttotal: £894 (6 )

Cozy 1 Bedroom Unit Located In A Condo/hotel In The Heart Of Coconut Grove-free Parking

1 4
apartment , Miami
This one-bedroom flat is located in Coconut Grove, a short walk from the Cocowalk Shopping Centre and within a 5-kilometre radius of several other popular Miami destinations. This property has received excellent ratings for location, cleanliness and user experience.
The flat has one bathroom and can accommodate up to four guests. It offers a fully equipped kitchen, a washer/dryer, a balcony, a swimming pool, a fitness centre, and parking.
Our Naples Hideaway - Caribbean
10 78 reviews
Caribbean
01/11 – 15/11
£191/nighttotal: £2674 (14 )

Our Naples Hideaway

3 6
apartment , Naples Park
This Naples Park apartment, near Vanderbilt Beach (1.8km) and Delnor-Wiggins Pass State Park (a short 18-minute walk), offers convenient access to coastal attractions.
This three-bedroom, two-bathroom property boasts a private pool, fully equipped kitchen, free Wi-Fi, private parking, and a terrace with garden views, comfortably accommodating families or groups.
Paraiso De Verano - Caribbean
9.5 13 reviews
Caribbean
27/06 – 04/07
£61/nighttotal: £427 (7 )

Paraiso De Verano

3 4
apartment , Santiago de los Caballeros
This Santiago de los Caballeros apartment, near Kaskada Park, is conveniently located approximately 7.2 kilometres from the Heroes of the Restoration Monument and Leon Center.
The 104-square-metre property offers three bedrooms, a private pool, free Wi-Fi, parking, and access to a fitness centre, billiards, and children's play equipment.
Apartamentos Chalet Del Mar - Caribbean
9.0 520 reviews
Caribbean
05/07 – 12/07
£34/nighttotal: £238 (7 )

Apartamentos Chalet Del Mar

1 2
apartment , San Andrés
Apartamentos Chalet del Mar offers self-catering apartments near San Luis and Cove Bay, San Andrés, conveniently located 6km from San Andrés Bay and 7km from North End.
Each apartment at Apartamentos Chalet del Mar features a fully equipped kitchen with a fridge and microwave, a private bathroom, air conditioning, a terrace, and access to a garden; complimentary Wi-Fi is also provided.

Best Caribbean short term rentals with laundry available

Spectacular 7th Floor Apartment - Caribbean
9.6 21 reviews
Caribbean
01/11 – 15/11
£108/nighttotal: £1512 (14 )

Spectacular 7th Floor Apartment

2 6
apartment , Playa Juan Dolio
This two-bedroom, two-bathroom apartment in Villas Del Mar, Playa Juan Dolio, is conveniently located 0.6 km from Marbella Beach and 3.9 km from Los Marlins Golf Course.
The 140 square metre property boasts a fully equipped kitchen, private balcony, swimming pool, fitness centre, and jacuzzi, comfortably accommodating up to six guests.
Residencial Christall Ap 2-a - Caribbean
9.5 247 reviews
Caribbean
27/09 – 04/10
£37/nighttotal: £259 (7 )

Residencial Christall Ap 2-a

2 2
apartment , Santiago de los Caballeros
Residencial Christall apartment 2-A is conveniently located in Santiago de los Caballeros, Dominican Republic, approximately 5.3km from the Cibao Stadium, 6.1km from the Monumento a los Héroes de la Restauración, and 5.8km from the Leon Center.
This 80 square metre, two-bedroom flat offers free private parking, a fully equipped kitchen, air conditioning, Wi-Fi, and a terrace; guests can also enjoy the on-site garden and benefit from 24-hour reception services.
Mystic Ridge Paradise - Caribbean
9.3 105 reviews
Caribbean
20/08 – 24/08
£167/nighttotal: £668 (4 )

Mystic Ridge Paradise

2 3
apartment , Ocho Rios
Mystic Ridge Paradise is a short walk from two popular beaches in Ocho Rios, offering a convenient base for exploring the area. The property has received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom apartment features a fully equipped kitchen, a private pool with stunning lake views, and a hot tub. Guests can enjoy amenities like a bar, spa, tennis court, and access to streaming services, making it a perfect choice for a relaxing and enjoyable stay.
Luxury Apartment 2 Br/2 Bath Steps From Ocean - Caribbean
9.4 130 reviews
Caribbean
12/10 – 18/10
£80/nighttotal: £480 (6 )

Luxury Apartment 2 Br/2 Bath Steps From Ocean

3 2
apartment , Punta Cana
This Bávaro apartment, a short walk from the Aromas Museum and Los Corales Beach, is less than 2km from Cortecito Beach and the Cocotal Golf and Country Club.
The two-bedroom, two-bathroom flat offers a fully equipped kitchen, free Wi-Fi, a swimming pool, and terrace; it comfortably sleeps a family or group, and is located near multiple beaches and a golf course.
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