Caribbean Islands holiday rentals

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Best Caribbean Islands holiday rentals

Most recommended holiday rentals in Caribbean Islands

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Montego Bay Club Apartments - Montego Bay - Pool
Montego Bay Club Apartments
Ocean Front
7.4Good(222)
Parking
Free Wi-Fi
Pool
Air conditioning
R2 154+
Check availability
Snug Harbour View Condo #6 - George Town - Pool
Snug Harbour View Condo #6
George Town, Cayman Islands
9.0Wonderful(1)
Parking
Free Wi-Fi
Pool
Air conditioning
R5 798+
Check availability
Anna's Joye Chatham - Montego Bay - Pool
Anna's Joye Chatham
Montego Bay, Jamaica
9.7Wonderful(19)
Parking
Free Wi-Fi
Pool
Air conditioning
R4 162+
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Rose View Apartment - Montego Bay - Living room
Rose View Apartment
Montego Bay, Jamaica
9.4Wonderful(49)
Parking
Free Wi-Fi
Air conditioning
R2 248+
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Remarkable 1-Bed Apartment in Montego Bay - Montego Bay - Kitchen
Remarkable 1-Bed Apartment in Montego Bay
Montego Bay, Jamaica
8.6Very Good(6)
Parking
Free Wi-Fi
Pool
Air conditioning
R1 691+
Check availability
Anna's Joye Seawind - Freeport, Montego Bay - Montego Bay - Beach
Anna's Joye Seawind - Freeport, Montego Bay
Ocean Front
9.3Wonderful(37)
Parking
Free Wi-Fi
Pool
Air conditioning
R2 360+
Check availability
Cayman Imperial Suite-Close to Beaches, Restaurants, Bus-stops & Stores - George Town - Kitchen
Cayman Imperial Suite-Close to Beaches, Restaurants, Bus-stops & Stores
George Town, Cayman Islands
Free Wi-Fi
Air conditioning
R3 178+
Check availability
Bella Vista Vacation - Montego Bay
Bella Vista Vacation
Paradise Acers - Mango Walk
8.0Very Good(128)
Parking
Free Wi-Fi
Pool
Air conditioning
R2 323+
Check availability
Casa de Bells 2 - George Town - Building
Casa de Bells 2
George Town, Cayman Islands
9.9Wonderful(27)
Parking
Free Wi-Fi
Pool
Air conditioning
R3 679+
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Snug Harbour View Condo #2 - George Town - Pool
Snug Harbour View Condo #2
George Town, Cayman Islands
9.3Wonderful(2)
Parking
Free Wi-Fi
Pool
Air conditioning
R5 417+
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Snug Harbour View Condo #5 - George Town - Pool
Snug Harbour View Condo #5
George Town, Cayman Islands
6.7Okay(2)
Parking
Free Wi-Fi
Pool
Air conditioning
R5 489+
Check availability
Mel-Bella Retreat - George Town - Living room
Mel-Bella Retreat
George Town, Cayman Islands
Air conditioning
R3 586+
Check availability
Snug Harbour View Condo #4 - George Town - Pool
Snug Harbour View Condo #4
George Town, Cayman Islands
9.2Wonderful(4)
Parking
Free Wi-Fi
Pool
Air conditioning
R5 320+
Check availability
Cayman Reef Resort #52 - George Town - Pool
Cayman Reef Resort #52
George Town, Cayman Islands
9.0Wonderful(3)
Parking
Free Wi-Fi
Pool
Air conditioning
R8 009+
Check availability
New 3-bed on Hip Strip, Beach access, Sleeps 8 - Montego Bay
New 3-bed on Hip Strip, Beach access, Sleeps 8
Montego Bay, Jamaica
8.0Very Good(2)
Parking
Free Wi-Fi
Pool
Air conditioning
R6 615+
Check availability
Viking Hill Oceanfront Hostel & Resort - Nassau
Viking Hill Oceanfront Hostel & Resort
Cable Beach
6.4Okay(315)
Parking
Free Wi-Fi
Pool
Air conditioning
R1 394+
Check availability
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R0 - R5 036R5 036 - R10 053R10 053 - R15 089R15 089 - R20 106R20 106+ per night

Property Types

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

May

High season

December

Average price (weeknight)

R7 050

Average price (weekend night)

R6 256
Cheapest month to stay with an average 25% drop in price.
Most expensive month to stay with an average 24% 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

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 R291. Search here for similar prices

  • 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, towers, villas, boats, bungalows, cabins, chalets, cottages, houseboats, treehouses, campsites, luxury tents, agritourism, castles, studios, caravans, barns and motorhomes.

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

    If you’re looking for something special, the holiday rental most loved by KAYAK users is The Beach House.

  • 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 8% allowing you to bring your pet along with you.

See more FAQs

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.

What Caribbean Islands holiday rental guests are talking about

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Holiday rentals by topic

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Posada Colonial Beach Villas - San Juan - Dining room
Posada Colonial Beach Villas
Santurce
8.6Very Good(483)
Parking
Free Wi-Fi
Air conditioning
R2 434+
Check availability
Numero Uno Beach Apartments - San Juan
Numero Uno Beach Apartments
Santurce
8.0Very Good(41)
Free Wi-Fi
Pet-friendly
Air conditioning
R6 556+
Check availability

Popular topics

Everything you need to know for your stay in Caribbean Islands

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