Caribbean Islands vacation rentals

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Latest Caribbean Islands vacation rental deals

MOST POPULARMontego Bay
Vacation homes from $23
Nassau
Vacation homes from $44
San Juan
Vacation homes from $41
Oranjestad
Vacation homes from $54
Punta Cana
Vacation homes from $34
Providenciales
Vacation homes from $156

Best Caribbean Islands vacation rentals

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$0 - $149$149 - $297$297 - $445$445 - $593$593+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Caribbean Islands

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Skycastle Oasis - Ocho Rios
Skycastle Oasis
Ocho Rios, Jamaica
8.8Very good(50)
Parking
Free Wi-Fi
Pool
$124+
Check availability
Cozy apartment near the beach #1 - Fajardo
Cozy apartment near the beach #1
Fajardo, Puerto Rico
8.3Very good(72)
Parking
Free Wi-Fi
$125+
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Ventnor House Apartments - Bridgetown
Ventnor House Apartments
Bridgetown, Barbados
9.1Wonderful(75)
Parking
Free Wi-Fi
$127+
Check availability
El Amanecer del Este 2 - Fajardo
El Amanecer del Este 2
Fajardo, Puerto Rico
8.4Very good(7)
Parking
Free Wi-Fi
$150+
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Fajardo Peaceful Place - Fajardo
Fajardo Peaceful Place
Fajardo, Puerto Rico
9.5Wonderful(6)
Parking
Free Wi-Fi
$150+
Check availability
Tradewinds Apartments Simpson Bay - Simpson Bay - Balcony
Tradewinds Apartments Simpson Bay
Simpson Bay, St. Maarten
9.2Wonderful(101)
Free Wi-Fi
Pool
$154+
Check availability
Amazing 2 bedroom apt 1 warm cosy comfortable - St. John's - Living room
Amazing 2 bedroom apt 1 warm cosy comfortable
St. John's, Antigua And Barbuda
5.9Fair(14)
Parking
Free Wi-Fi
$159+
Check availability
Naütik, Ocean Front! Great View - Fajardo
Naütik, Ocean Front! Great View
Fajardo, Puerto Rico
8.8Very good(111)
Parking
Free Wi-Fi
Pool
Pet friendly
$167+
Check availability
Master Beachfront Studios Seven Seas - Fajardo - Beach
Master Beachfront Studios Seven Seas
Fajardo, Puerto Rico
7.5Good(2)
Parking
Free Wi-Fi
$170+
Check availability
Rockley Golf 810 is a 2 bedroom, 2 Bathroom 1st floor Apartment with pool - Bridgetown - Pool
Rockley Golf 810 is a 2 bedroom, 2 Bathroom 1st floor Apartment with pool
Bridgetown, Barbados
7.7Good(3)
Parking
Free Wi-Fi
Pool
$172+
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Suenos del Mar - Fajardo - Beach
Suenos del Mar
Fajardo, Puerto Rico
8.7Very good(385)
Parking
Free Wi-Fi
$192+
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Isla Verde Puerto Rico, One Queen Bed - Carolina
Isla Verde Puerto Rico, One Queen Bed
Carolina, Puerto Rico
8.0Very good(10)
Parking
Free Wi-Fi
Pool
$206+
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Isla Verde Modern Apartment with Pool - San Juan
Isla Verde Modern Apartment with Pool
San Juan, Puerto Rico
6.7Okay(16)
Parking
Free Wi-Fi
Pool
$220+
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Waterfront studio at Fajardo, Puerto Rico - Fajardo
Waterfront studio at Fajardo, Puerto Rico
Fajardo, Puerto Rico
9.2Wonderful(161)
Parking
Free Wi-Fi
Pool
$264+
Check availability
Romantic Getaway! Book Now! Amazing Views & Perfect for 2! Close to Pools - Saint Thomas Island - Building
Romantic Getaway! Book Now! Amazing Views & Perfect for 2! Close to Pools
East End
9.5Wonderful(30)
Free Wi-Fi
Pool
$315+
Check availability
Marina Vista St. Thomas - Saint Thomas Island - Balcony
Marina Vista St. Thomas
East End
9.5Wonderful(16)
Parking
Free Wi-Fi
Pool
Pet friendly
$501+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

August
December
$393
$352
Cheapest month to stay with an average 34% drop in price.
Most expensive month to stay with an average 66% 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 vacation rental

  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Caribbean Islands for 6 days.
  • The cheapest Caribbean Islands vacation rental found on KAYAK in the last 2 weeks was $46, while the most expensive was $522.
  • Vacation rentals in Caribbean Islands are around 42% 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 vacation homes is Negril, with around 276 properties and an average price of $54. The most popular vacation rentals in Caribbean Islands among KAYAK users are Villas Sur Mer, Bak A Yaad, and Idle Awhile The Cliffs.

FAQs when booking a vacation home in Caribbean Islands

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

    In the last 72 hours, users have found Caribbean Islands vacation rentals for tonight for as low as $32. Search here for similar prices

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

    The average price for a weekly Caribbean Islands vacation rental found by KAYAK users in the last 2 weeks is $2,121.

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

    The average price for a monthly Caribbean Islands vacation rental found by KAYAK users in the last 2 weeks is $9,091.

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

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

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

    There are many types of properties available for Caribbean Islands vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Perle d'Or City Apartments and Viking Hill Oceanfront Hostel & Resort.

  • What are the most popular Caribbean Islands vacation rentals for a large group?

    If you’re a large group then you’ll need plenty of space. The highest rated vacation homes that can sleep 6 people or more by KAYAK users are Rhyne Park Inn, Luxury 2BR Home facing Beach w/Pool Montego Bay #3 and Royal Hideaway.

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

    There are a number of dog and pet-friendly Caribbean Islands vacation rentals, with around 10% 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 vacation home.

What Caribbean Islands vacation rental guests are talking about

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Popular topics

Vacation rentals by topic

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Playa Turquesa Ocean Club - Punta Cana
Playa Turquesa Ocean Club
Punta El Cortecito
8.5Very good(40)
Free Wi-Fi
Pool
$250+
Check availability
Posada Colonial Beach Villas - San Juan - Dining room
Posada Colonial Beach Villas
Santurce
8.6Very good(488)
Parking
Free Wi-Fi
$153+
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Coqui del Mar Guesthouse - San Juan - Kitchen
Coqui del Mar Guesthouse
Santurce
8.8Very good(117)
Parking
Free Wi-Fi
Pool
Pet friendly
$231+
Check availability
Mar Del Norte - San Juan - Room amenity
Mar Del Norte
San Juan, Puerto Rico
8.9Very good(1335)
Parking
Free Wi-Fi
$149+
Check availability
Calle Aponte- Near Beach and Arts District - San Juan
Calle Aponte- Near Beach and Arts District
Santurce
9.2Wonderful(77)
Free Wi-Fi
$57+
Check availability
Numero Uno Beach Apartments - San Juan - Beach
Numero Uno Beach Apartments
Santurce
8.0Very good(39)
Free Wi-Fi
Pet friendly
$289+
Check availability
La Capitana Old San Juan Building - San Juan - Bedroom
La Capitana Old San Juan Building
San Juan Antiguo
6.5Okay(748)
Free Wi-Fi
Pool
$142+
Check availability

Everything you need to know for your stay in Caribbean Islands

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