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

Bamboo House 3 With Private Pool (8 Min To Beach) - Caribbean
9.5 183 reviews

Bamboo House 3 With Private Pool (8 Min To Beach)

apartment
This Rincon holiday home is situated in a peaceful rural setting, just 3 kilometres from Sandy Beach, Rincon Central Plaza, and Balneario Pico de Piedra. The property has consistently received excellent ratings from guests for its cleanliness, location, and overall experience.
The house has two bedrooms and one bathroom, comfortably accommodating up to six guests. It features a private pool, a balcony, a garden, and parking, making it ideal for families or groups seeking a relaxing and enjoyable getaway.
Las Palmas - Caribbean
10 4 reviews

Las Palmas

apartment, Santiago de los Caballeros
This three-bedroom flat in Las Palmas, Santiago de los Caballeros, offers convenient access to attractions including Leon Center (3.4 km), La Aurora Cigar Factory (3.2 km), and Monumento a los Heroes de la Restauracion (6.9 km).
This 82 square metre apartment accommodates up to 11 guests and features a balcony with mountain views, complimentary on-site parking, free WiFi, a garden, and an on-site mini-market.
Private Beach Front Cottage - Caribbean
9.6 55 reviews

Private Beach Front Cottage

cottage, Christiansted
This oceanfront cottage is located just 1.5km from the Casino at the Divi Carina Bay and Grape Tree Beach, and less than 2km from the Reef Golf Course, making it ideal for exploring the beautiful surroundings of Christiansted. The cottage has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The cottage has one bedroom and one bathroom, accommodating up to three guests. Enjoy a range of amenities including a private pool, a terrace, a garden, and a fully equipped kitchen with a fridge and microwave.
Beautiful Beach Apartment At Sandy Beach, Rincon - Caribbean
9.7 351 reviews

Beautiful Beach Apartment At Sandy Beach, Rincon

apartment
This apartment is situated just a 5-minute walk from Sandy Beach and Playa Pools, within 3 kilometres of Playa María and Playa Punta Higuero, offering easy access to Rincon's beautiful coastline. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The home has three bedrooms, accommodating up to eight guests, making it ideal for families or groups of friends. The apartment also boasts a range of amenities including a swimming pool, garden, terrace, and parking, providing a comfortable and convenient stay.

Best Caribbean short term rentals with a balcony

Private Tropical Villa With Great Views - Caribbean
9.3 8 reviews

Private Tropical Villa With Great Views

house
This one-bedroom house is situated in a peaceful neighbourhood just 8 kilometres from Christiansted, the historical capital of Saint Croix, offering easy access to shops, restaurants, and attractions.
The house features a patio with stunning views, a garden, and parking, perfect for a couple seeking a relaxing retreat with easy access to the island's attractions.
Unbelievable Views & Sounds Of The Sea - Caribbean
9.3 174 reviews

Unbelievable Views & Sounds Of The Sea

apartment
This apartment is located in La Pared, just 0.3 kilometres from La Pared Beach and 2.7 kilometres from Luquillo Beach, offering easy access to both stunning beaches. The apartment has received excellent ratings for its cleanliness, location and overall experience.
The apartment is a one-bedroom, one-bathroom property with a floor area of 67 square metres, comfortably accommodating up to two guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a garden, a fitness centre, parking, and a terrace with lovely views.
Penthouse 50m Plage / Piscines / Bars-restos /Wifi - Caribbean
9.3 85 reviews

Penthouse 50m Plage / Piscines / Bars-restos /Wifi

apartment
This beachfront apartment in central Las Terrenas is a short walk from La Iglesia Beach, Playa Ballenas, and Beach Garden Plaza, with the Haitian Caraïbes Art Gallery and Plaza Rosada Shopping Centre within a 15-minute radius (approximately 2.4km).
This 155 square metre, two-bedroom, two-bathroom apartment sleeps four guests and boasts a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a spa, concierge service, parking, and excellent user and location ratings.
Hospitality Expert Cb1 Pool Beach Chef - Caribbean
9.3 1422 reviews

Hospitality Expert Cb1 Pool Beach Chef

house, Montego Bay
This two-bedroom property is situated in Montego Bay, just a short walk from Half Moon Point Beach and a 2.5-mile drive from Sangster International Airport. It has received excellent ratings for its location, cleanliness, and overall user experience.
The 100 square metre home boasts a private pool with stunning views, a fully equipped kitchen, and a terrace with sea views. Guests can enjoy a range of amenities, including a spa, a fitness centre, a tennis court, and a bar.

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

Beach Paradise Apartments - Caribbean
9.5 83 reviews

Beach Paradise Apartments

apartment, San Andrés
Beach Paradise Apartments are located in the Los Almendros neighbourhood, just 1 kilometre from Gustavo Rojas Pinilla International Airport, offering a peaceful retreat close to the beach. The apartment has received excellent ratings for cleanliness and user experience, with a very good location rating.
This self-catering property features a private terrace, a fully equipped kitchen with a microwave, fridge, and stovetop, and comfortable bedding with towels and linen provided. Guests can also enjoy satellite TV, air conditioning, and parking.
Sea Breeze In The Creek - Caribbean
10 6 reviews

Sea Breeze In The Creek

apartment
This Creek beachfront bungalow offers unparalleled ocean views, directly on the sea.
The one-bedroom bungalow, sleeping up to four guests, features a kitchen with fridge and microwave, air conditioning, a swimming pool, garden, and a sea-facing porch; further details on proximity to Creek's attractions are needed.
3 Bdrm Up To 6 Guest Pool Walk To Vanderbilt Beach - Caribbean
9.9 258 reviews

3 Bdrm Up To 6 Guest Pool Walk To Vanderbilt Beach

apartment, Naples Park
This newly remodelled, non-smoking flat in North Naples is situated under 1 kilometre from Vanderbilt Beach and The Mercato, with downtown Naples a 10-minute drive away.
This 3-bedroom, 2-bathroom residence sleeps 6 guests and features a private outdoor space with a swimming pool and hot tub, alongside a modern kitchen equipped with a fridge, microwave, and dishwasher.
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.

Best Caribbean short term rentals with laundry available

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
This West End Negril apartment, a six-minute walk from the Negril Cliffs and a nine-minute (5.6km) drive from Seven Mile Beach, offers easy access to Negril's key attractions.
The two-bedroom, one-bathroom flat sleeps five, features a fully equipped kitchen with oven, stovetop, fridge, and laundry facilities, plus a swimming pool and parking, making it ideal for families.
Upscale 1br, Near Blue Mall | Rooftop| Yellowkey - Caribbean
9.6 143 reviews

Upscale 1br, Near Blue Mall | Rooftop| Yellowkey

apartment
This apartment is located in Downtown Santo Domingo, within walking distance of Acropolis Center and Blue Mall, and within 2km of Agora Mall and the Gate of San Diego. The property has received excellent ratings for its location, cleanliness, and overall experience.
The one-bedroom apartment comfortably accommodates two guests and features a well-equipped kitchen, two bathrooms, a washing machine, a balcony, and a TV. Guests can enjoy access to a fitness centre, a garden, and parking, along with the convenience of air conditioning and internet access.
Dom. Rep. Exclusive 2 Bed Apt. Evaristo Morales - Caribbean
9.7 51 reviews

Dom. Rep. Exclusive 2 Bed Apt. Evaristo Morales

apartment, Santo Domingo
This Santo Domingo apartment rental is situated in the Evaristo Morales district, a 1.6km walk from Blue Mall, 2.7km from Agora Mall, and 1.6km from the city centre, offering easy access to Santo Domingo's attractions.
The two-bedroom, three-bathroom flat features a fully equipped kitchen, free Wi-Fi, private parking, a terrace, and access to a fitness centre and garden; it comfortably accommodates families or groups of up to six.
Amazing Rooftop And Best View Of The City - Caribbean
9.7 61 reviews

Amazing Rooftop And Best View Of The City

apartment, Santiago de los Caballeros
This Santiago de los Caballeros apartment is conveniently located near the Monumento a los Héroes de la Restauración, a short 1.4 km walk away, and within 1.4 km of Estadio Cibao FC.
The self-catering flat offers a one-bedroom layout with two bathrooms, a fully equipped kitchen, free Wi-Fi, private parking, a rooftop pool, fitness centre and sun terrace; sleeping up to two guests and providing easy access to the city's landmarks.
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