Caribbean Short term rentals

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

Apartamento En Residencial Privado - Caribbean
9.7 115 reviews

Apartamento En Residencial Privado

apartment
This recently renovated three-bedroom apartment in San Isidro, Santo Domingo, is situated 12.2 kilometres from Puerto Santo Domingo and 14.8 kilometres from the Malecon.
The self-catering property offers free Wi-Fi, private parking, a swimming pool, garden, terrace, and airport transfers, sleeping up to six guests and boasting two bathrooms, a fully equipped kitchen, and city views.
Our Place 2 - Caribbean
9.2 391 reviews

Our Place 2

studio, San Andrés
This studio apartment is located just one block from the beach in the North End district of San Andrés, close to North End beach, San Andres Bay, and Spratt Bight. It has received very good ratings for cleanliness and user experience and an excellent rating for location.
The studio has its own kitchen and is one of three independent units on the first floor. You can enjoy a terrace, a garden, parking, and free Wi-Fi, as well as air conditioning.
Los Bohios Campo Añil - Caribbean
8.9 183 reviews

Los Bohios Campo Añil

farm, Jarabacoa
Los Bohios Campo Añil is a farm stay in Jarabacoa, situated just 11 miles from the Salto de Jimenoa waterfall and 25 miles from Kaskada Park, offering a peaceful escape in the beautiful countryside. The property has received very good user ratings, excellent location ratings, and very good cleanliness ratings.
The farm stay offers a single bedroom and bathroom in a 20 square metre space. Guests can enjoy a restaurant, bar, garden, terrace, swimming pool, and free Wi-Fi and parking, along with activities like cycling and a children's playground.
New 3 Br/2ba Apartment With A/c, Wifi And Pool! - Caribbean
9.5 28 reviews

New 3 Br/2ba Apartment With A/c, Wifi And Pool!

apartment
This apartment is located in Santiago de los Caballeros, just 2.9 kilometres from the city centre, making it convenient for exploring both the cultural attractions of Centro Leon and the shopping opportunities of Bella Terra Mall. It has consistently received excellent ratings for location, cleanliness and user experience.
The property has three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a washing machine, air conditioning, a swimming pool, a garden, a fitness centre, free Wi-Fi, a Smart TV, parking and barbecue facilities.

Best Caribbean short term rentals with a balcony

El Conde Del Macao - Caribbean
9.5 34 reviews

El Conde Del Macao

apartment, El Macao
This apartment is situated in El Macao, just 16 kilometres from Cana Bay Golf Club and Punta Blanca, and 22 kilometres from Cocotal Golf and Country Club. The apartment has been highly rated by previous guests, receiving excellent marks for cleanliness and location, and a very good overall rating.
The apartment offers a comfortable 60 square metre space with one bathroom. Guests can enjoy a private pool and garden, a terrace with pool views, a fully equipped kitchen, barbecue facilities, and a range of activities including fishing, bicycle and car rental, and a paid airport shuttle service.
King Bed & Mini Golf, Pet Friendly! Cowboy Pool Close To Beach Airport & Zoo Bbq - Caribbean
9.4 27 reviews

King Bed & Mini Golf, Pet Friendly! Cowboy Pool Close To Beach Airport & Zoo Bbq

cottage, West Palm Beach
This charming cottage is located in Parker Ridge, a peaceful neighbourhood within easy reach of West Palm Beach Municipal Golf Course and Palm Beach Zoo. It has consistently received excellent guest reviews, highlighting its comfortable and convenient features.
The cottage provides spacious accommodation for up to seven guests, with three bedrooms, two bathrooms and a total floor area of 93 square metres. It offers a range of amenities including a private swimming pool, a Jacuzzi, a garden, a terrace, a fully equipped kitchen and free Wi-Fi access.
Modern Home In Aguadilla,w/16k Generator/water Res - Caribbean
9.8 124 reviews

Modern Home In Aguadilla,w/16k Generator/water Res

apartment
This three-bedroom house is located in Aguadilla, just a short distance from the town centre and within easy reach of beaches, the Aguadilla Lighthouse and the historical downtown area. The property has received excellent ratings for its location, cleanliness and overall experience, making it a popular choice for families and groups of friends.
The house offers a spacious and comfortable layout, with a fully equipped kitchen, a living room with a large TV, and three bedrooms, each with a TV. Enjoy a relaxing escape with a private pool and gazebo area, equipped with a BBQ grill, perfect for outdoor dining and entertaining.
Vibrant Apartment Near Beach, Eats & Shops. - Caribbean
9.4 194 reviews

Vibrant Apartment Near Beach, Eats & Shops.

apartment
This San Juan apartment is situated above a commercial building in a convenient district, offering easy access to local amenities such as a coffee shop, clothing store, burger joint, and nail salon, and is a short walk from the beach.
The 70 square metre flat comprises two bedrooms, two bathrooms, a small kitchen with a fridge, microwave, and coffee machine, plus a terrace, garden, and parking; it comfortably sleeps four and is ideal for travellers seeking a base near San Juan's restaurants and beaches.

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! Prioritising depends on the island, but generally, you could explore a major city like San Juan, Puerto Rico, visiting Castillo San Felipe del Morro and Castillo San Cristobal. Alternatively, you could focus on beach relaxation and watersports in Barbados or explore the lush rainforests and waterfalls of Dominica. Consider visiting a rum distillery – Mount Gay Rum in Barbados is a popular choice – and enjoying some local cuisine.
  • What attractions should one visit when spending a month in the Caribbean?

    A month allows for island hopping! Perhaps start in Cuba, exploring Havana's old town and experiencing its vibrant culture. Then, fly to Jamaica, visiting Dunn's River Falls and exploring the Blue Mountains. Next, consider the quieter islands like St. Lucia, known for its Pitons, or explore the diverse ecosystems of the Bahamas. A month gives ample time for deeper exploration, including hiking, diving, and cultural immersion in multiple locations.
  • Can visitors to the Caribbean witness any unique natural cycles, like cherry blossom season or autumn colours?

    The Caribbean doesn't experience autumn colours in the same way as temperate regions. The climate is tropical or subtropical, so the foliage remains largely green year-round. However, you can witness blooming flowers depending on the season and specific island; various orchids and hibiscus are common sights, their blooming periods varying slightly.
  • 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 ones in Bridgetown, Barbados, or Port-au-Prince, Haiti. Engage in conversations with vendors, learning about their produce and daily life. Attend local festivals, like Carnival in Trinidad and Tobago, or Crop Over in Barbados. Consider taking a cooking class to learn how to prepare traditional dishes. Staying in locally owned guesthouses rather than large resorts also fosters deeper interaction.
  • Are there any distinctive cultural activities or hands-on workshops available in the Caribbean?

    Absolutely! Many islands offer workshops in traditional crafts like pottery making (try searching for workshops in Jamaica or the Dominican Republic), weaving (common in many islands), and even rum making (several distilleries offer tours and workshops). Music and dance classes, focusing on reggae, calypso, or soca, are also readily available, often found through local community centres or tourism offices.
  • What are some secret spots or hidden treasures to visit in the Caribbean?

    The Caribbean holds many hidden gems. Exploring less-visited islands like Nevis or Anguilla offers a tranquil escape. Seek out secluded beaches accessible only by boat, or discover hidden waterfalls and hiking trails away from the main tourist areas – research specific islands for recommendations. For example, the Valley of Desolation in St. Lucia is a stunning, less-crowded natural wonder.
  • What should not be left out of your suitcase if you are going to the Caribbean?

    Pack light, breathable clothing suitable for hot and humid weather. Don't forget swimwear, sunscreen (high SPF is crucial!), insect repellent, a hat, sunglasses, and comfortable walking shoes for exploring. A reusable water bottle is essential for hydration. Consider a light raincoat for unexpected showers.
  • What are the most popular festivals in the Caribbean?

    Carnival in Trinidad and Tobago is world-renowned, a vibrant spectacle of music, dance, and costumes. Crop Over in Barbados is another major celebration, featuring parades and music. Junkanoo in The Bahamas is a unique street parade with colourful costumes and music. These are just a few examples; many islands have their own unique festivals throughout the year.
  • Where should one try the best local food in the Caribbean?

    The best local food is often found in smaller, family-run restaurants away from the main tourist areas. Explore local markets and street food stalls for authentic flavours. Each island has its specialities; jerk chicken in Jamaica, conch fritters in The Bahamas, and mofongo in Puerto Rico are just a few examples. Ask locals for recommendations – they'll often point you to hidden culinary gems.

Best Caribbean short term rentals with a kitchen

Lugar Agradable Y Una Rica Vista A La Piscina Li I - Caribbean
9.8 105 reviews

Lugar Agradable Y Una Rica Vista A La Piscina Li I

apartment
This La Vega holiday home, perfect for families, is situated in [Insert District Name, La Vega], within a 2km radius of the Catedral de La Vega and 3km from the Museo del Tabaco.
The one-bedroom, two-bathroom property sleeps six, boasting a kitchen with fridge, microwave, and dishwasher, plus air conditioning, a swimming pool, garden, fitness centre, and parking; pets are welcome.
Idle Time On The Bay Relaxing Beautiful Serene - Caribbean
9.9 201 reviews

Idle Time On The Bay Relaxing Beautiful Serene

apartment
This waterfront apartment is located just 3km from Montego Bay Cruise Ship Terminal and Fairview Shopping Centre, offering easy access to the town's attractions while enjoying the peaceful surroundings of Freeport Peninsula and Sunset Beach Resort Au Natural Beach. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features one bedroom and one bathroom, comfortably accommodating up to three guests. Amenities include a fully equipped kitchen, a washing machine, free Wi-Fi, a balcony, a swimming pool, a jacuzzi, a sauna, and parking.
Sweet Spot Studio In Pga Village 2 Beds B - Caribbean
9.1 383 reviews

Sweet Spot Studio In Pga Village 2 Beds B

studio, Port St. Lucie
This one-bedroom apartment in Carlton, Port St. Lucie is ideally located for exploring the area, with the PGA Village just a short drive away and Fort Pierce Inlet State Park a 17-mile journey. It's rated excellent for location, cleanliness, and user experience, making it a great option for travellers looking for a comfortable and convenient stay.
The apartment comfortably accommodates up to four guests, and features a fully equipped kitchen, a private pool and garden, and a hot tub for relaxation. Enjoy the Florida sunshine on the terrace with garden views, and take advantage of the on-site fitness centre, spa, and barbecue facilities.
Jahiem's Paradise - Caribbean
9.5 16 reviews

Jahiem's Paradise

apartment
This luxury villa is located in Lancewood Meadows, a secure gated community just 10 kilometres from Ocho Rios' attractions, including Dunn's River Falls and Mystic Mountain.
This 3-bedroom, 3.5-bathroom villa accommodates up to 7 guests and features a fully equipped kitchen, air conditioning, high-speed Starlink internet, a swimming pool, and a fitness centre, all powered by solar energy.

Best Caribbean short term rentals with laundry available

Resort Like Amenities - In The City 2 - Caribbean
10 2 reviews

Resort Like Amenities - In The City 2

apartment, Kingston
This Kingston flat is situated 15 minutes by car from the airport and 5-15 minutes from major hospitals, dining, and entertainment hubs.
This 2-bedroom, 2-bathroom apartment accommodates up to 4 guests and features resort-style amenities including a swimming pool, a playground, a rooftop deck with city views, and a fully equipped kitchen with a Starbucks coffee bar.
The Rise Estate Hideaway Premium - Caribbean
10 10 reviews

The Rise Estate Hideaway Premium

apartment
This five-bedroom, five-bathroom luxury villa, accommodating up to ten guests, is located in an exclusive gated community in Cabarete, just 500 metres from Hideaway Beach and minutes from the renowned kite and windsurfing spot of Encuentro Beach. The residence offers air conditioning, Wi-Fi, a fully equipped chef's kitchen with premium appliances, and spa-inspired jetted tubs, alongside 24/7 security and reliable electricity, ensuring a comfortable and secure stay for families and enthusiasts alike.
Entire Beach Homesteps To Beachsolar5 Beds-wifi - Caribbean
9.6 89 reviews

Entire Beach Homesteps To Beachsolar5 Beds-wifi

apartment
This studio apartment is situated in Aguadilla Pueblo, just a short walk from the beach and the town centre.
The 28 square metre apartment is equipped with a kitchenette, a private outdoor shower, and free public street parking.
Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West - Caribbean
8.6 85 reviews

Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West

cottage, Cudjoe Key
This charming waterfront cottage is located just 3km from Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offering easy access to the surrounding area's attractions. The property has received very good ratings from previous guests.
The cottage provides 2 bedrooms and 1 bathroom in a 70 square meter space, comfortably accommodating 4 guests. It boasts a fully equipped kitchen, air conditioning, a private swimming pool, a terrace, a garden, and parking, as well as access to the water for fishing, kayaking, or simply relaxing by the shore.
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