Holiday lettings & accommodation in the Caribbean - HomeToGo base64Hash Holiday lettings & accommodation in the Caribbean - HomeToGo

Holiday lettings & accommodation in the Caribbean

Find 125,345 available offers from 117 partners
Caribbean
Anytime
Guests
Caribbean
Anytime
Guests

Popular Filters to discover the perfect holiday home in the Caribbean

House
2 Adults
Pets allowed
Hot tub
Pool
Cottage
Cabin

With a Caribbean holiday cottage, you can enjoy postcard-worthy turquoise beaches, unspoilt nature and a relaxed lifestyle like no other.


From the culture and history of Jamaica to the stunning nature of St. Lucia and the pristine beaches of Guadeloupe, a stay in a holiday villa in the Caribbean is sure to make for unforgettable memories. Staying in a traditional Caribbean cottage with its own swimming pool is the ideal way to make the most of island life.

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Holiday rentals with wifi

Whether it's for working remotely or streaming your favourite shows, internet access can be an indispensable amenity when it comes to choosing a holiday home. Check out HomeToGo's range of holiday lettings with WiFi in the Caribbean and enjoy a fast and reliable internet connection during your stay.

House  North Eleuthera
31 Aug - 7 Sept
-55%
£546
£244 per night
House ∙ 6 guests ∙ 2 bedrooms

Pleasant Holiday Home in North Eleuthera with Garden & Pool

North Eleuthera, The Bahamas
Internet
Details
HomeToGo
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House  North Side
7 Sept - 14 Sept
-80%
£1,197
£244 per night
House ∙ 9 guests ∙ 3 bedrooms

Nice Holiday Home in North Side with Barbecue, Garden & Pool

North Side, Cayman Islands
Free cancellation
Internet
Details
HomeToGo
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Condo  Pelican Key
24 Aug - 31 Aug
-41%
£124
£73 per night
Condo ∙ 4 guests ∙ 1 bedroom

Flat in Pelican Key with Hot Tub, Pool & Barbecue

Pelican Key, Cole Bay, Sint Maarten
Free cancellation
Internet
Details
HomeToGo
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Holiday lettings and apartments with air conditioning

Good weather while on holiday is always great - and it's a plus to be able to control the temperature in your accommodation too. Find holiday homes and apartments in the Caribbean with air conditioning and cooling systems to ensure maximum comfort during your stay.

House  Le Vauclin
22 Jun - 29 Jun
-8%
£80
£73 per night
House ∙ 2 guests ∙ 1 bedroom

Beautiful Holiday Home in Le Vauclin with Terrace, Barbecue & Pool

Le Vauclin, Martinique
Air conditioning
Details
HomeToGo
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Studio flat  Sainte-Anne
29 Jun - 6 Jul
-23%
£47
£37 per night
Studio flat ∙ 4 guests ∙ 1 bedroom

Nice Studio in Sainte-Anne with Furnished Terrace

4.0
Very good (1 rating)
Sainte-Anne, Martinique
Air conditioning
Details
HomeToGo
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House  Sainte-Luce
10 May - 17 May
-23%
£106
£81 per night
House ∙ 4 guests ∙ 2 bedrooms

Lovely House in Sainte-Luce with Pool, Terrace & Garden

4.9
Outstanding (39 ratings)
Sainte-Luce, Martinique
Air conditioning
Details
HomeToGo
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Apartments and holiday lettings with a kitchen

Looking for self-catering accommodation in the Caribbean? Find the perfect letting for you with our selection of Caribbean holiday rentals with kitchens. Well-appointed and equipped with plenty of cooking appliances, these holiday homes are great for self-catered stays.

Apartment  Saint Joseph
7 Sept - 14 Sept
-14%
£38
£33 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Flat in Saint Joseph with Garden, Barbecue & Terrace

4.5
Excellent (4 ratings)
Saint Joseph, Arrondissement of Fort-de-France, Martinique
Kitchen
Details
HomeToGo
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House  Le Moule
22 Mar - 29 Mar
-44%
£48
£27 per night
House ∙ 2 guests ∙ 1 bedroom

House in Le Moule with Terrace, Barbecue & Garden

Le Moule, Grande-Terre, Guadeloupe
Kitchen
Details
HomeToGo
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Apartment  Les Trois-Îlets
1 Feb - 8 Feb
-50%
£55
£28 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Flat in Les Trois-Îlets

4.0
Very good (1 rating)
Les Trois-Îlets, Martinique
Kitchen
Details
HomeToGo
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Best holiday rental deals in the Caribbean

Save up to 22%

Cottage Carolina
1 Sept - 8 Sept
-6%
£182
£172 per night
Cottage ∙ 6 guests ∙ 1 bedroom

Cottage in Carolina with Terrace & Barbecue + Gorgeous Views

4.9
Outstanding (190 ratings)
Carolina, Calabash Boom, U.S. Virgin Islands
Details
Vrbo
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House Sainte-Anne
17 May - 24 May
-22%
£106
£82 per night
House ∙ 4 guests ∙ 2 bedrooms

Holiday Home in Sainte-Anne with Outdoor Terrace

Sainte-Anne, Martinique
Details
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House East End
1 Sept - 8 Sept
-8%
£360
£332 per night
House ∙ 6 guests ∙ 2 bedrooms

Holiday Home in East End with Private Pool + Gorgeous View

4.8
Outstanding (124 ratings)
East End, St. John, U.S. Virgin Islands
Details
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Book a top quality accommodation from £27 per night by searching and comparing the 125,345 properties listed in Caribbean. HomeToGo allows you to instantly search and compare the offers for each rental from different providers to find the best deal and save up to 39%.

Recommended holiday lettings in the Caribbean

Rent a holiday home, apartment or cottage in the Caribbean from just £27 per night

Apartment Dominicus
6 Jul - 13 Jul
-17%
£74
£61 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Beautiful Holiday Apartment in Dominicus with Large Balcony + Close to Beach

5.0
Outstanding (6 ratings)
Dominicus, Bayahibe, Dominican Republic
Details
Vrbo
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Condo Nazareth
1 Sept - 8 Sept
£235 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Flat in Nazareth with Large Pool

4.8
Outstanding (14 ratings)
Nazareth, East End, U.S. Virgin Islands
Details
Vrbo
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Apartment Grand Roy
6 Jul - 13 Jul
-17%
£42
£35 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Flat in Grand Roy with Garden

4.5
Excellent (7 ratings)
Grand Roy, Saint John, Grenada
Details
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Condo Simpson Bay
7 Sept - 14 Sept
-41%
£124
£73 per night
Condo ∙ 4 guests ∙ 1 bedroom

Pleasant Flat in Simpson Bay with Barbecue, Pool, Hot Tub

5.0
Outstanding (1 rating)
Simpson Bay, Sint Maarten
Free cancellation
Details
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House Red Hook
27 Jul - 3 Aug
£196 per night
House ∙ 4 guests ∙ 2 bedrooms

Wonderful Holiday Home in Red Hook with Barbecue + Great View

4.9
Outstanding (34 ratings)
Red Hook, East End, U.S. Virgin Islands
Details
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House Bouillante
7 Jul - 14 Jul
£38 per night
House ∙ 2 guests ∙ 1 bedroom

Lovely House in Bouillante with Private Parking

4.8
Outstanding (4 ratings)
Bouillante, Basse-Terre, Guadeloupe
Details
HolidayLettings
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Condo Golden Rock
1 Sept - 8 Sept
£377 per night
Condo ∙ 8 guests ∙ 4 bedrooms

Nice Flat in Golden Rock with Free-Form Pool + Beachfront View

4.8
Outstanding (4 ratings)
Golden Rock, Sion Farm, U.S. Virgin Islands
Details
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Apartment West Bay
7 Sept - 14 Sept
-57%
£484
£208 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Flat in West Bay

West Bay, Cayman Islands
Free cancellation
Details
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Condo Frydendal
1 Sept - 8 Sept
£479 per night
Condo ∙ 9 guests ∙ 4 bedrooms

Flat in Frydendal with Pool, Garden & Terrace

4.9
Outstanding (11 ratings)
Frydendal, East End, U.S. Virgin Islands
Details
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Budget-friendly Holiday Homes in the Caribbean

Find Fantastic yet Cheap Lettings

Villa Chocolate Hole
1 Sept - 8 Sept
-7%
£622
£578 per night
Villa ∙ 6 guests ∙ 3 bedrooms

Villa in Chocolate Hole with Oversized Pool + 180-Degree Views

5.0
Outstanding (12 ratings)
Chocolate Hole, Cruz Bay, U.S. Virgin Islands
Details
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Condo Simpson Bay
24 Aug - 31 Aug
-41%
£124
£73 per night
Condo ∙ 4 guests ∙ 1 bedroom

Charming Flat in Simpson Bay with Barbecue, Pool, Hot Tub

Simpson Bay, Sint Maarten
Free cancellation
Details
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Apartment Le Lamentin
5 Aug - 12 Aug
-51%
£68
£34 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday Apartment in Le Lamentin with Garden, Barbecue & Terrace

4.7
Excellent (34 ratings)
Le Lamentin, Arrondissement of Fort-de-France, Martinique
Details
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Top-Rated Lettings and Properties in the Caribbean

Book Holiday Letting Offers with the Highest User Rating

Condo East End
1 Sept - 8 Sept
£264 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Spacious Flat in East End with Pool, Barbecue & Terrace + Unobstructed Views

4.8
Outstanding (178 ratings)
East End, St. Thomas, U.S. Virgin Islands
Details
Vrbo
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House Enighed
27 Jul - 3 Aug
£452 per night
House ∙ 5 guests ∙ 2 bedrooms

House in Enighed with Garden, Barbecue & Terrace + Ocean View

4.9
Outstanding (130 ratings)
Enighed, Cruz Bay, U.S. Virgin Islands
Details
Vrbo
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House Naguabo
7 Sept - 14 Sept
-4%
£318
£306 per night
House ∙ 10 guests ∙ 4 bedrooms

Holiday Home in Naguabo with Private Pool + Mountain Views

4.7
Excellent (21 ratings)
Naguabo, Puerto Rico
Details
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Popular holiday rental amenities in the Caribbean

  • Pool (79,735)
  • WiFi (115,572)
  • Air conditioning (112,421)
  • Grill (45,324)
  • Balcony/patio (77,031)
  • Kitchen (99,491)
  • Washing machine (72,559)
  • Garden (70,988)
  • Microwave (76,734)
  • TV (106,076)
  • No smoking (113,506)
  • Parking (5,165)

You will have a lot of accommodation options to compare and from which to choose if you are looking for a rental providing a pool in Caribbean. Our data show that more apartment rental include pools than hotel room. Also, they can welcome 5 holidaymakers, on average, while hotel room with pools can accommodate an average of 7 visitors. In Caribbean, more than half of the holiday rentals providing a pool are close to the water.

Price and Availability Index for Caribbean

Click on any bar to see price and availability information

Holiday Letting Price Information in the Caribbean

The graph shows average prices of holiday lettings in the Caribbean for the next twelve months. Holiday letting prices are the highest in April (26/04 – 03/05). Conversely, the cheapest average prices are in one week of June (15/06 – 22/06).

Rental availability information in the Caribbean

The availability graph shows the percentage of available rentals in the Caribbean. The busiest time to book a holiday letting in the Caribbean so far is in May (24/05 – 31/05), where only 11 rentals are available. In contrast, only 46% of the holiday homes are booked during a week in June (29/06 – 06/07).

7-Day Weather Forecast in the Caribbean

Wed, 12 Jun
33°
30°

10%

4 h

16 km/h

Thu, 13 Jun
32°
29°

10%

3 h

16 km/h

Fri, 14 Jun
32°
29°

10%

3 h

19 km/h

Sat, 15 Jun
32°
31°

5%

3 h

21 km/h

Sun, 16 Jun
33°
30°

10%

3 h

18 km/h

Mon, 17 Jun
32°
23°

10%

2 h

11 km/h

Tue, 18 Jun
31°
29°

15%

2 h

12 km/h

Where to find the best food in the Caribbean?

Caribbean Culinary Adventures

While travellers come to the Caribbean for fun in the sun, many come back for the delicious cuisine. After a day laying by the pool of your villa, sample all the flavours island life has to offer. Menus at both upmarket bistros and relaxed hangouts usually include seafood prepared in various ways. Flying fish and grouper are menu highlights found in restaurants and grills across the different islands. If you like your food very spicy, trying jerk spice mix on meat is a must-try. Roast pork is another Caribbean classic.

For those looking for a first-class dining experience, sophisticated dining is easy to find on the Caribbean islands. French bistros with extensive wine selections abound. Make sure to make a reservation if you wish to dine in some of the most popular restaurants. Of course, more laid-back options are also available all over the islands. You will find low-key beach-front eateries, barefoot-style grills and easygoing cafes with delicious offerings to enjoy alfresco.

Where are the unique attractions in the Caribbean?

Shimmering Waters and Amazing Activities

Caribbean islands host stunning beaches that offer a large range of activities to enjoy, all on gorgeous turquoise waters. The conditions are perfect for a wide array of water-based fun, with warm and crystal-clear waters.

Antigua is ideal for scuba-diving, with its coral canyons and marine wildlife. So are the Bahamas with their tropical fish and incredible shipwrecks. Others will love learning kiteboarding or windsurfing in St. Martin or jet-skiing in St Barts. Barbados is a very popular destination for surfers from all over the world, offering waves on the east, north and south coasts.

Information about holiday rentals in the Caribbean

🏡 Holiday homes available 125,345 rentals
💳 Discounts available up to 39%
🌙 Nightly prices from £27
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly rentals 10,294 properties
🏊 Holiday rentals with pools 79,572 properties
390 reviews
Caribbean holiday rentals have an average rating of 3.9/5 across 390 reviews left by travellers.

Frequently Asked Questions

How many accommodation are available to book in the Caribbean?

June is the time of year with the highest amount of Apartment rental and Villa available in the Caribbean, so you'll find plenty of great holiday deals during this month.

What is the most popular holiday home amenity in the Caribbean?

Three most popular holiday rental amenities among our customers in the Caribbean are Pool, Internet and Air conditioning.

How many holiday lettings with a pool there are on offer in the Caribbean?

Holiday homes with pools are 63 of all offers in the Caribbean for an average cost of £589 per night.

Am I allowed to bring my pet during my stay in a Caribbean holiday home?

There are 10,294 holiday rentals in the Caribbean that allow pets with an average price of £394 per night.

What's the best time of year to travel to Caribbean?

Sun lovers should visit Caribbean in June and July to enjoy the warmest weather.

Where can I see deals on holiday rentals in the Caribbean?

You can find great value holiday lettings in the Caribbean with prices for a let starting at just £27 - and HomeToGo has introduced a range of features that make it easy to discover some outstanding offers. If you're still selecting dates for a trip, search with HomeToGo's flexible dates technology to quickly locate low-price date options and see discounts of up to 39%. Furthermore, HomeToGo's 'distance from' filter enables you to discover hidden gem holiday homes in lower-price, under-the-radar spots which are still near to the area of your choice, whether that's sand and sea, a mountain for snowboarding, or a city's urban hub. Book early to take advantage of the greatest variety of options and low prices - and do so without worries by clicking on HomeToGo's 'free cancellation' filter as you look for the perfect holiday home.

What are the benefits of booking a holiday letting in the Caribbean with HomeToGo?

From increased privacy away from the crowds to plenty of room for relaxing with your loved ones, holiday homes in the Caribbean provide plenty of benefits. HomeToGo surfaces real reviews written by previous guests, and searching is secure, easy, and stress-free - so with 125,345 deals from 117 providers in the vicinity, you're bound to locate the ideal place to stay with all of the amenities that are important to you in the Caribbean.

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