Caribbean Islands holiday rentals

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Latest Caribbean Islands holiday rental deals

MOST POPULARMontego Bay
Holiday homes from $150

Best Caribbean Islands holiday rentals

Most recommended holiday rentals in Caribbean Islands

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Choose To Be Happy at EI8HT! - Super Studios and Penthouse Apartment - Kingston - Building
Choose To Be Happy at EI8HT! - Super Studios and Penthouse Apartment
Kingston, Jamaica
9.2Wonderful(100)
Parking
Free Wi-Fi
$226+
View availability
Dream 36 @ Montego Bay - Montego Bay - Bedroom
Dream 36 @ Montego Bay
Montego Bay, Jamaica
9.0Wonderful(1)
Free Wi-Fi
$398+
View availability
Kaikushi - Noord - Balcony
Kaikushi
Noord, Aruba
9.5Wonderful(27)
Parking
Free Wi-Fi
Pool
$337+
View availability
The Gardens - Kingston - Bedroom
The Gardens
Kingston, Jamaica
8.0Very Good(73)
Parking
Free Wi-Fi
Pool
$276+
View availability
Movida Inn Aruba - Noord - Beach
Movida Inn Aruba
Noord, Aruba
10Wonderful(10)
Free Wi-Fi
Pool
Spa
$314+
View availability
Dickenson Bay Oasis at Antigua Village - Cedar Grove - Beach
Dickenson Bay Oasis at Antigua Village
Cedar Grove, Antigua And Barbuda
8.5Very Good(377)
Parking
Free Wi-Fi
Pool
$478+
View availability
Yepton Estate Cottages - St. John's - Bedroom
Yepton Estate Cottages
St. John's, Antigua And Barbuda
9.2Wonderful(20)
Parking
Free Wi-Fi
Pool
$540+
View availability
Divi Village Villas - Oranjestad - Lobby
Divi Village Villas
Oranjestad, Aruba
10Wonderful(2)
Parking
Free Wi-Fi
Pool
$1,109+
View availability
Serenity Villas And Suites - Playa Los Corales - Punta Cana - Balcony
Serenity Villas And Suites - Playa Los Corales
Punta Cana, Dominican Republic
7.7Good(114)
$263+
View availability
Casa Costera, Isla Verde Beach, Apartments by Marriott Bonvoy - San Juan - Building
Casa Costera, Isla Verde Beach, Apartments by Marriott Bonvoy
San Juan, Puerto Rico
8.2Very Good(29)
Free Wi-Fi
Pool
Pet-friendly
$521+
View availability
Xeliter Cana Rock Punta Cana - Punta Cana - Living room
Xeliter Cana Rock Punta Cana
Punta Cana, Dominican Republic
7.6Good(31)
Parking
Free Wi-Fi
Pool
$209+
View availability
Old San Juan Rentals - San Juan - Living room
Old San Juan Rentals
San Juan Antiguo
8.1Very Good(534)
Free Wi-Fi
$322+
View availability
Star of The Olympus - San Juan - Bedroom
Star of The Olympus
Santurce
6.7Okay(58)
Free Wi-Fi
$173+
View availability
Gold Coast Aruba - Aurum Collection - Noord
Gold Coast Aruba - Aurum Collection
Noord, Aruba
9.3Wonderful(298)
Parking
Free Wi-Fi
Pool
$368+
View availability
Viking Hill Oceanfront Hostel & Resort - Nassau
Viking Hill Oceanfront Hostel & Resort
Cable Beach
6.4Okay(315)
Parking
Free Wi-Fi
Pool
$117+
View availability
Aruba Beach Villas - Oranjestad
Aruba Beach Villas
Oranjestad, Aruba
7.5Good(348)
Parking
Free Wi-Fi
Pool
$214+
View availability
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$9 - $239$239 - $467$467 - $695$695 - $923$923+ per night

Property type

ApartmentCondoCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

September

High season

December

Average price (weeknight)

$593

Average price (weekend night)

$479
Cheapest month to stay with an average 35% drop in price.
Most expensive month to stay with an average 50% 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 4 days.
  • Holiday rentals in Caribbean Islands are around 79% 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 1,137 properties and an average price of $308. The most popular holiday rentals in Caribbean Islands among KAYAK users are Dream 36 @ Montego Bay, Mobay Kotch, and Montego Bay Club Apartments.

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 $27. 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 $2,156.

  • 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 $9,239.

  • 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, cabins, cottages, campsites, luxury tents, chalets, ranches, boats, bungalows, agritourism, houseboats, treehouses, barns, motorhomes, 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 A1 Apartments Aruba.

  • 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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Numero Uno Beach Apartments - San Juan
Numero Uno Beach Apartments
Santurce
8.0Very Good(41)
Free Wi-Fi
Pet-friendly
$551+
View availability

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