Caribbean holiday homes and lettings - HomeToGo base64Hash Caribbean holiday homes and lettings - HomeToGo

Caribbean holiday homes and lettings

Find 137,828 available offers from 150 partners
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Top 15 Recommended holiday lettings in the Caribbean

Find your perfect holiday home, apartment or cottage in the Caribbean from just £34 per night!

Apartment Rendezvous And Ditleff
Apartment ∙ 16 guests ∙ 5 bedrooms

Flat with barbecue, private pool & garden | Nature view

Rendezvous And Ditleff, Cruz Bay, U.S. Virgin Islands
from £591
per night
Outstanding(86 ratings)
from £591
per night
View deal
Villa Judith's Fancy
Villa ∙ 12 guests ∙ 4 bedrooms

Villa with garden, private pool & terrace

Judith's Fancy, Sion Farm, U.S. Virgin Islands
from £866
per night
Outstanding(42 ratings)
from £866
per night
View deal
House Nassau
House ∙ 20 guests ∙ 7 bedrooms

Charming house with terrace, barbeque & private pool | Beach nearby

Nassau, New Providence, The Bahamas
from £467
per night
Excellent(80 ratings)
from £467
per night
View deal
Villa Coverley
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with garden, terrace & private pool | Perfect for remote work

Coverley, Christ Church, Barbados
from £124
per night
Outstanding(71 ratings)
from £124
per night
View deal
Villa Farmer's Hill
Villa ∙ 20 guests ∙ 6 bedrooms

Villa with private pool, terrace & barbeque

Farmer's Hill, Exuma, The Bahamas
from £1,464
per night
Outstanding(23 ratings)
from £1,464
per night
View deal
House Farmer's Hill
House ∙ 14 guests ∙ 4 bedrooms

Holiday home with BBQ, terrace & private pool

Farmer's Hill, Exuma, The Bahamas
from £687
per night
Outstanding(77 ratings)
from £687
per night
View deal
House Aguada
House ∙ 30 guests ∙ 12 bedrooms

Child-friendly holiday home with garden, private pool & barbeque | Nature view | Next to the beach

Aguada, Puerto Rico
from £820
per night
Outstanding(126 ratings)
from £820
per night
View deal
Condo Frydendal
Condo ∙ 9 guests ∙ 4 bedrooms

Flat with private pool, garden & terrace | Nature view | Good for workation

Frydendal, East End, U.S. Virgin Islands
from £325
per night
Outstanding(23 ratings)
from £325
per night
View deal
House North Side
House ∙ 14 guests ∙ 5 bedrooms

Children-friendly holiday home with terrace, barbecue & private pool

North Side, Cayman Islands
from £483
per night
Outstanding(90 ratings)
from £483
per night
View deal
Villa Grapetree
Villa ∙ 13 guests ∙ 5 bedrooms

Family-friendly big villa with barbeque & private pool | Sea view | Beach nearby | Suitable for remote work

Grapetree, East End, U.S. Virgin Islands
from £267
per night
Very good(2 ratings)
from £267
per night
View deal
Villa Central
Villa ∙ 12 guests ∙ 6 bedrooms

Villa with garden, terrace & private pool | Nature view

Central, St. John, U.S. Virgin Islands
from £1,070
per night
Outstanding(90 ratings)
from £1,070
per night
View deal
House Nassau
House ∙ 12 guests ∙ 6 bedrooms

Family-oriented pleasant holiday home with BBQ, terrace & garden | Perfect for remote work

Nassau, New Providence, The Bahamas
from £417
per night
Outstanding(32 ratings)
from £417
per night
View deal
House North Palmetto Point
House ∙ 14 guests ∙ 6 bedrooms

Family-friendly house with terrace, BBQ & private pool | Nature view | Close to the beach

North Palmetto Point, Central Eleuthera, The Bahamas
from £829
per night
Outstanding(89 ratings)
from £829
per night
View deal
Villa Grapetree
Villa ∙ 8 guests ∙ 4 bedrooms

Children-friendly villa with terrace, barbecue & garden | Nature view | Close to the beach

Grapetree, East End, U.S. Virgin Islands
from £618
per night
Outstanding(41 ratings)
from £618
per night
View deal
Villa Rum Point
Villa ∙ 12 guests ∙ 5 bedrooms

Children-friendly lovely villa with terrace, garden & private pool | Nature view | Perfect for remote work

Rum Point, North Side, Cayman Islands
from £668
per night
Outstanding(96 ratings)
from £668
per night
View deal

Holiday lettings and apartments with air conditioning

Villa  Rum Point
from £668 per night
Villa ∙ 10 guests ∙ 5 bedrooms

Villa with barbecue, terrace & garden | Good for workation

4.9
Outstanding(96 ratings)
Rum Point, North Side, Cayman Islands
Air conditioning
View deal
Villa  Coral Bay
from £855 per night
Villa ∙ 8 guests ∙ 4 bedrooms

Villa with private pool & barbeque

4.8
Outstanding(34 ratings)
Coral Bay, St. John, U.S. Virgin Islands
Air conditioning
View deal
Villa  Rendezvous And Ditleff
from £576 per night
Villa ∙ 6 guests ∙ 3 bedrooms

Villa with garden, terrace & barbeque | Mountain view

5.0
Outstanding(56 ratings)
Rendezvous And Ditleff, Cruz Bay, U.S. Virgin Islands
Air conditioning
View deal
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Best holiday homes with a patio or terrace

House  Higuillar
from £121 per night
House ∙ 12 guests ∙ 6 bedrooms

House with pool, barbeque & garden | Nature view | Good for workation

4.6
Excellent(25 ratings)
Higuillar, Dorado, Puerto Rico
Balcony/Patio
View deal
House  Santurce
from £934 per night
House ∙ 14 guests ∙ 5 bedrooms

Holiday home with garden, private pool & terrace

5.0
Outstanding(94 ratings)
Santurce, San Juan, Puerto Rico
Balcony/Patio
View deal
House  North Side
from £427 per night
House ∙ 15 guests ∙ 6 bedrooms

House with terrace, private pool & barbeque | Nature view | Suitable for remote work

5.0
Outstanding(111 ratings)
North Side, Cayman Islands
Balcony/Patio
View deal
See all offers

Holiday homes and cottages with a garden

House  Palmer
from £735 per night
House ∙ 14 guests ∙ 6 bedrooms

Children-friendly charming house with terrace, private pool & BBQ

4.2
Very good(16 ratings)
Palmer, Mameyes II, Puerto Rico
Garden
View deal
Villa  Anna's Retreat
from £523 per night
Villa ∙ 10 guests ∙ 3 bedrooms

Villa with garden, private pool & terrace | Mountain view | Perfect for remote work

5.0
Outstanding(99 ratings)
Anna's Retreat, Tutu, U.S. Virgin Islands
Garden
View deal
House  Gros Islet
from £232 per night
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly nice holiday home with terrace, garden & private pool | Mountain view | Good for workation

4.8
Outstanding(23 ratings)
Gros Islet, Saint Lucia
Garden
View deal
See all offers

Budget-friendly Holiday Homes in the Caribbean

Find Fantastic yet Cheap Lettings

Villa Belair
from £1,110 per night
Villa ∙ 24 guests ∙ 8 bedrooms

Villa with private pool, barbecue & terrace | Mountain view

5.0
Outstanding(23 ratings)
Belair, Little Bay, Sint Maarten
View deal
Villa Cruz Bay
from £689 per night
Villa ∙ 10 guests ∙ 5 bedrooms

Villa with terrace, barbecue & hot tub

5.0
Outstanding(81 ratings)
Cruz Bay, St. John, U.S. Virgin Islands
View deal
House Borinquen
from £851 per night
House ∙ 16 guests ∙ 6 bedrooms

House with barbecue, garden & terrace

4.9
Outstanding(106 ratings)
Borinquen, Aguadilla, Puerto Rico
View deal

Top-Rated Lettings and Properties in the Caribbean

Book Holiday Letting Offers with the Highest User Rating

Villa Fish Bay
from £506 per night
Villa ∙ 22 guests ∙ 7 bedrooms

Fully equipped villa with private pool, garden & barbecue

5.0
Outstanding(17 ratings)
Fish Bay, Cruz Bay, U.S. Virgin Islands
View deal
House North Palmetto Point
from £470 per night
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented house with terrace, BBQ & private pool | Close to the beach

5.0
Outstanding(93 ratings)
North Palmetto Point, Central Eleuthera, The Bahamas
View deal
House James Pt
from £593 per night
House ∙ 10 guests ∙ 4 bedrooms

Holiday home with private pool, barbeque & hot tub

4.9
Outstanding(82 ratings)
James Pt, North Eleuthera, The Bahamas
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform holiday planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in the Caribbean

  • Pool (85,708)
  • WiFi (123,648)
  • Air conditioning (125,094)
  • Grill (46,814)
  • Balcony/patio (80,297)
  • Kitchen (109,997)
  • Washing machine (81,904)
  • Garden (74,662)
  • Microwave (81,053)
  • TV (115,300)
  • No smoking (121,259)
  • Parking (5,192)

You will have plenty of holiday rentals to compare and from which to choose if you are looking for an accommodation offer offering a pool in Caribbean. Holiday rentals with pools in Caribbean cost, on average, £570 per night. Most of the listed properties with pools are apartment rental. You can also rent accommodation providing a pool near the water, which is the case for nearly half of the rentals there.

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 upcoming months. Holiday letting prices are the highest in December (27/12 – 03/01). On the other hand, in October you will find the cheapest prices (04/10 – 11/10). The average price this week is £231 a night.

Rental availability information in the Caribbean

Our availability graph helps you identify the busiest months in the Caribbean. In one week of May (30/05 – 06/06), 90% of the holiday homes are booked. It will be easy to find a holiday home that suits you in one week in August (02/08 – 09/08), when 63 of the rentals are still available.

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.

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 137,828 rentals
🌙 Nightly prices from £34
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly rentals 22,234 properties
🏊 Holiday rentals with pools 85,606 properties
653 reviews
Caribbean holiday rentals have an average rating of 4.1/5 across 653 reviews left by travellers.

Frequently Asked Questions

What is the average nightly rate for a holiday rental in the Caribbean?

The average starting price for a holiday cottage or rental in the Caribbean is £34 per night. Prices vary depending on the type of holiday let, season, and amenities. Use HomeToGo to compare deals and find the best value for your trip.

How many holiday homes are available to rent in the Caribbean? And what are the most popular types of holiday lets?

There are 137,828 holiday lettings in the Caribbean to choose from and book for your next trip. The most popular types of holiday lets in the Caribbean include apartment rental and villa. These are perfect for groups of around 4 people, offering comfort and flexibility. Discover the most booked options quickly with HomeToGo’s smart filters.

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

When booking a holiday apartment in the Caribbean, consider looking for a place with Pool, Internet, or Air conditioning, which are the three most popular amenities for this destination.

Do you offer holiday homes with a swimming pool in the Caribbean?

Looking for a pool? You’ll find that nearly half of holiday cottages and homes in the Caribbean have one. Whether you’re travelling with kids or just want a splash, you’re sorted with 85,606 options available. Use HomeToGo to browse offers with pools and book your dream holiday rental!

What's the perfect time to travel to Caribbean?

June and July are the warmest months in the Caribbean, while June and July have less rain.

Can you get deals on holiday rentals in the Caribbean?

You can get brilliant bargains on holiday rentals in the Caribbean with the nightly price of a letting starting at just £34 - and HomeToGo has launched plenty of features that make it quick and simple to find some outstanding deals. If you don't have set dates for your holiday, make use of HomeToGo's flexible dates technology to quickly locate great value date options and find savings of up to 10%. Moreover, HomeToGo's 'distance from' filter can help you discover top quality accommodation offers in great value, lesser-known locales with good proximity to the area of your choice, whether that's the coastline, a swimming lake, winter sports area or town centre. Start searching with time to spare to get the benefits of the greatest variety of options and top discounts - and do so with confidence by utilising HomeToGo's 'free cancellation' filter as you look for the perfect holiday home.

What are the pros of booking a holiday home in the Caribbean with HomeToGo?

From increased privacy away from the crowds to more space in which to chill out with your travel companions, holiday homes in the Caribbean offer many benefits. HomeToGo surfaces real reviews written by previous guests, and searching is secure, easy, and stress-free - so with 137,828 offers from 145 providers in the area, you're guaranteed to uncover the perfect place to stay with the amenities and features that are important to you in the Caribbean.

Do you offer holiday accommodation for couples in the Caribbean?

There are lovely holiday homes in the Caribbean designed with couples in mind. Whether you’re after seclusion or a city break, there’s something for every type of trip. Let HomeToGo help you plan your next romantic break.

Can I book a waterfront holiday rental in the Caribbean?

Yes, you’ll find 129269 holiday rentals near the water in the Caribbean, whether it’s a beach, lake or river. These spots are perfect for a morning coffee with a view or lazy days by the water. Filter your search by ‘Near water’ on HomeToGo to see your options.

Why should I book my holiday rental with HomeToGo?

HomeToGo brings together over 15 million holiday rentals from trusted providers, so you can find the best deal in one place. Our smart search makes it easy to find what suits you. Book with confidence and enjoy support every step of the way.

Can I find family-friendly holiday lettings in the Caribbean?

Yes, there are lots of family-friendly holiday homes in the Caribbean. Top options can host groups of up to 4, perfect for holidays with kids or extended family. Use HomeToGo to explore family-friendly holiday cottages with ease.

Can I cancel my holiday rental booking for free?

Free cancellation is available on lots of holiday homes, depending on the provider. Look for rentals with free cancellation to keep things stress-free.

Is it possible to rent a holiday home for a weekend getaway in the Caribbean?

Yes, many holiday lets in the Caribbean offer flexible booking options, including weekend stays. It’s perfect for a quick break without using too many holiday days. Find yours easily on HomeToGo.

Are there any last-minute holiday rental deals in the Caribbean?

Yes, HomeToGo regularly features last-minute holiday deals in the Caribbean, perfect for spontaneous getaways. With HomeToGo, you can find great value — and save up to 10%, even at short notice. Check often and book quickly to grab the best offers.

Find more holiday rental types in the Caribbean

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