Caribbean Islands holiday rentals

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Latest Caribbean Islands holiday rental deals

MOST POPULARMontego Bay
Holiday homes from £34
Nassau
Holiday homes from £173
Bridgetown
Holiday homes from £60

Best Caribbean Islands holiday rentals

Exclusive villa Grace Islands Turcas - Providenciales - Building
Exclusive villa Grace Islands Turcas
Providenciales, Turks and Caicos Islands
Villa
Free Wi-Fi
Air conditioning
£1,296+
Check availability
Seafire Residence N503 - West Bay - Lounge
Seafire Residence N503
West Bay, Cayman Islands
Apartment
Free Wi-Fi
Air conditioning
£1,748+
Check availability
Lesville Tobago - Crown Point - Pool
Lesville Tobago
Crown Point, Trinidad and Tobago
7.6Good(4)
Apartment
Parking
Free Wi-Fi
Pool
Air conditioning
£43+
Check availability
The Emerald villa - Ocho Rios - Bedroom
The Emerald villa
Ocho Rios, Jamaica
7.2Good(8)
House
Air conditioning
£131+
Check availability
Sophisticated Residence steps away from the Beach located at The Ritz-Carlton - West Bay - Living room
Sophisticated Residence steps away from the Beach located at The Ritz-Carlton
West Bay, Cayman Islands
10Wonderful(1)
Condo
Free Wi-Fi
Air conditioning
£3,662+
Check availability
Barco A La Vista - Grand Cayman - George Town - Lounge
Barco A La Vista - Grand Cayman
George Town, Cayman Islands
Villa
Air conditioning
£3,699+
Check availability
Villa located on Grace Bay Beach - Providenciales - Balcony
Villa located on Grace Bay Beach
Providenciales, Turks and Caicos Islands
Villa
Air conditioning
£1,040+
Check availability
Ocho Rios Beach House at Dax Hall - Ocho Rios - Living room
Ocho Rios Beach House at Dax Hall
Ocho Rios, Jamaica
House
Free Wi-Fi
Air conditioning
£167+
Check availability
Luxury condo steps from one of the world's best beaches. - George Town - Beach
Luxury condo steps from one of the world's best beaches.
George Town, Cayman Islands
10Wonderful(6)
Condo
Free Wi-Fi
Air conditioning
£993+
Check availability
Ri'Biero's Holiday Apartments - Crown Point - Pool
Ri'Biero's Holiday Apartments
Crown Point, Trinidad and Tobago
8.7Very Good(42)
Apartment
Free Wi-Fi
Air conditioning
£114+
Check availability
Regal Beach Club 112-Stunning Condo-Fabulous Complex-Walking distance to all! - George Town - Pool
Regal Beach Club 112-Stunning Condo-Fabulous Complex-Walking distance to all!
George Town, Cayman Islands
9.9Wonderful(24)
Condo
Air conditioning
£605+
Check availability
Renovated Private Residence located at The Ritz-Carlton - West Bay - Kitchen
Renovated Private Residence located at The Ritz-Carlton
West Bay, Cayman Islands
Condo
Free Wi-Fi
Air conditioning
£3,646+
Check availability
Seamist 308 Views Of North Sound - West Bay - Building
Seamist 308 Views Of North Sound
West Bay, Cayman Islands
10Wonderful(1)
Apartment
Parking
Free Wi-Fi
Pool
Air conditioning
£282+
Check availability
Tranquil Breeze no cleaing fee - Bodden Town - Bedroom
Tranquil Breeze no cleaing fee
Bodden Town, Cayman Islands
10Wonderful(1)
House
Air conditioning
£160+
Check availability
Harbour Club Villas & Marina - Grace Bay - Pool
Harbour Club Villas & Marina
Grace Bay, Turks and Caicos Islands
Villa
Free Wi-Fi
Air conditioning
£328+
Check availability
One Luxe Jamaica Villa With Private Pool, Modern Interior And Secluded - Ocho Rios
One Luxe Jamaica Villa With Private Pool, Modern Interior And Secluded
Ocho Rios, Jamaica
8.8Very Good(9)
Villa
Parking
Free Wi-Fi
Pool
Air conditioning
£190+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

July
February
£164
£196
Cheapest month to stay with an average 41% drop in price.
Most expensive month to stay with an average 9% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Caribbean Islands holiday rental

  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Caribbean Islands for 10 days.
  • The cheapest Caribbean Islands holiday rental found on KAYAK in the last 2 weeks was £34, while the most expensive was £190.
  • Holiday rentals in Caribbean Islands are around 53% cheaper than hotels on average. Search here to compare prices for all accommodation types in Caribbean Islands.
  • The city in Caribbean Islands with the most affordable holiday homes is Montego Bay, with around 906 properties and an average price of £30. The most popular holiday rentals in Caribbean Islands among KAYAK users are Dream 36 Montego Bay, Serenitys Hideaway Montego Bay, and Angels Hideaway Blue Room.

FAQs when booking a holiday home in Caribbean Islands

  • How much is a holiday rental in Caribbean Islands for tonight?

    In the last 72 hours, users have found Caribbean Islands holiday rentals for tonight for as little as £20. Search here for similar prices

  • How much is a holiday rental for a week in Caribbean Islands?

    The average price for a weekly Caribbean Islands holiday rental found by KAYAK users in the last 2 weeks is £208.

  • How much is a holiday rental for a month in Caribbean Islands?

    The average price for a monthly Caribbean Islands holiday rental found by KAYAK users in the last 2 weeks is £893.

  • What types of holiday rentals are available in Caribbean Islands?

    There are loads of different property types that you can make your holiday home in Caribbean Islands. You’ll find apartments, campgrounds, condos, farm stays, houses, homestays, lodges, villas, cottages, cabins, campsites, luxury tents, bungalows, chalets, houseboats, treehouses, resorts, barns, caravans, hotels, boats, agritourism, bed & breakfasts, studios and castles.

  • What are some of the most-loved holiday rentals available in Caribbean Islands?

    There are many types of properties available for Caribbean Islands holiday rentals. If you’re looking for something special, holiday rentals most loved by KAYAK users are Ocean Spray Apartments and Melbourne Apartments.

  • Are there any pet-friendly holiday rentals in Caribbean Islands?

    There are a number of dog and pet-friendly Caribbean Islands holiday rentals, with around 5% allowing you to bring your pet along with you.

Where to stay in Caribbean Islands?

Our map will help you find the perfect place to stay in Caribbean Islands by showing you the exact location of each holiday home.

Everything you need to know for your stay in Caribbean Islands