Caribbean Islands vacation rentals

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Latest Caribbean Islands vacation rental deals

MOST POPULARMontego Bay
Vacation homes from $14
Nassau
Vacation homes from $40
San Juan
Vacation homes from $22
Oranjestad
Vacation homes from $55
Punta Cana
Vacation homes from $27
Providenciales
Vacation homes from $138

Best Caribbean Islands vacation rentals

Apartamento La Paz - La Romana - Beach
Apartamento La Paz
La Romana, Dominican Republic
Apartment
$96+
Check availability
Peninsula Esmeralda Luxury Hotel & Villas - Puerto Plata - Pool
Peninsula Esmeralda Luxury Hotel & Villas
Puerto Plata, Dominican Republic
9.5Wonderful(11)
Villa
Parking
Free Wi-Fi
Pool
Spa
$155+
Check availability
Yepton Estate Cottages - St. John's - Bedroom
Yepton Estate Cottages
St. John's, Antigua And Barbuda
9.5Wonderful(19)
Cottage
Free Wi-Fi
Pool
$264+
Check availability
Blu Vista Cottages - Castries - Living room
Blu Vista Cottages
Castries, Saint Lucia
10Wonderful(1)
Apartment
Free Wi-Fi
$123+
Check availability
Aruba Beach Villas - Oranjestad - Beach
Aruba Beach Villas
Oranjestad, Aruba
8.0Very good(376)
Holiday Park
Parking
Free Wi-Fi
Pool
$216+
Check availability
Montego Bay Club Apartments - Montego Bay - Beach
Montego Bay Club Apartments
Ocean Front
7.2Good(265)
Apartment
Parking
Free Wi-Fi
Pool
$150+
Check availability
Union Hilltop Paradise Villas - Castries - Balcony
Union Hilltop Paradise Villas
Castries, Saint Lucia
8.0Very good(1)
Villa
Parking
Free Wi-Fi
Pool
$152+
Check availability
Eagle Stays Aruba-New Luxury, Cozy & Spacious Studio Near Eagle Beach! - Oranjestad - Beach
Eagle Stays Aruba-New Luxury, Cozy & Spacious Studio Near Eagle Beach!
Oranjestad, Aruba
10Wonderful(2)
Apartment
Parking
Free Wi-Fi
Pet friendly
$192+
Check availability
Patio Elba Boutique Hotel - San Juan - Dining room
Patio Elba Boutique Hotel
Santurce
8.9Very good(47)
Apartment
Free Wi-Fi
Pool
Pet friendly
$250+
Check 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
8.6Very good(52)
Apartment
Free Wi-Fi
Pool
Pet friendly
$358+
Check availability
Brisas Studio Apartments - Noord - Beach
Brisas Studio Apartments
Noord, Aruba
9.6Wonderful(345)
Apartment
Parking
Free Wi-Fi
Pool
$178+
Check availability
Mobay Kotch - Montego Bay - Balcony
Mobay Kotch
Center
8.6Very good(1128)
House
Free Wi-Fi
$51+
Check availability
Old San Juan Rentals - San Juan - Living room
Old San Juan Rentals
San Juan Antiguo
8.1Very good(534)
Apartment
Free Wi-Fi
$289+
Check availability
San Juan Home - San Juan
San Juan Home
Sabana Llana Norte
8.8Very good(259)
Apartment
Parking
Free Wi-Fi
$85+
Check availability
Viking Hill Oceanfront Hostel & Resort - Nassau
Viking Hill Oceanfront Hostel & Resort
Cable Beach
6.3Okay(372)
Apartment
Parking
Free Wi-Fi
Pool
$68+
Check availability
Chateau Nightwind - Saint Thomas Island
Chateau Nightwind
Northside
9.4Wonderful(38)
Villa
Parking
Free Wi-Fi
$383+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
April
$360
$357
Cheapest month to stay with an average 50% drop in price.
Most expensive month to stay with an average 51% 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 $42, while the most expensive was $1,667.
  • Vacation rentals in Caribbean Islands are around 60% 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 Santiago de los Caballeros, with around 628 properties and an average price of $45. The most popular vacation rentals in Caribbean Islands among KAYAK users are Senderos del botánico, Furnished apartment in a class A area, with new and modern furniture, and Torre de lujo con piscina y seguridad.

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 $29. 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 $3,723.

  • 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 $15,956.

  • 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, villas, resorts, cabins, cottages, holiday parks, hotels, luxury tents, houseboats, treehouses, barns, caravans, chalets, bungalows, boats, agritourism, bed & breakfasts, studios and castles.

  • 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 Divi Village Villas and Mangrove Beach Corendon 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 2BR Condo at Isla Verde Beach, Experience The Groovy Harbour House Lifestyle and Atlantis Paradise Island.

  • 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 4% 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.

Everything you need to know for your stay in Caribbean Islands