Caribbean Islands holiday rentals

Search hundreds of travel sites at once for holiday home deals in Caribbean Islands

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Best Caribbean Islands holiday rentals

Most recommended holiday rentals in Caribbean Islands

Show all
Divi Village Villas - Oranjestad - Lobby
Divi Village Villas
Oranjestad, Aruba
10Wonderful(2)
Parking
Free Wi-Fi
Pool
$1,193+
Check 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)
$283+
Check availability
Foyal Suites - Fort-de-France - Bathroom
Foyal Suites
Fort-de-France, Martinique
8.2Very Good(208)
Free Wi-Fi
$195+
Check 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
$225+
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
8.2Very Good(29)
Free Wi-Fi
Pool
Pet friendly
$560+
Check availability
Old San Juan Rentals - San Juan - Living room
Old San Juan Rentals
San Juan Antiguo
8.1Very Good(534)
Free Wi-Fi
$347+
Check availability
Star of The Olympus - San Juan - Bedroom
Star of The Olympus
Santurce
6.7Okay(58)
Free Wi-Fi
$186+
Check availability
La Esmeralda Pr - San Juan - Balcony
La Esmeralda Pr
Santurce
9.0Wonderful(56)
Free Wi-Fi
Pet friendly
$312+
Check availability
Monastery Suites - Oranjestad - Bedroom
Monastery Suites
Oranjestad, Aruba
7.6Good(83)
Free Wi-Fi
Pool
$158+
Check availability
Bak A Yaad - Negril
Bak A Yaad
Negril, Jamaica
8.5Very Good(271)
Parking
Free Wi-Fi
Pool
$89+
Check availability
Moonrisevillas - Negril
Moonrisevillas
Negril, Jamaica
8.5Very Good(131)
Parking
Free Wi-Fi
$245+
Check availability
Viking Hill Oceanfront Hostel & Resort - Nassau
Viking Hill Oceanfront Hostel & Resort
Cable Beach
6.4Okay(315)
Parking
Free Wi-Fi
Pool
$126+
Check availability
Aruba Beach Villas - Oranjestad
Aruba Beach Villas
Oranjestad, Aruba
7.5Good(348)
Parking
Free Wi-Fi
Pool
$230+
Check availability
Sapphire Village Condos - Saint Thomas Island
Sapphire Village Condos
East End
8.0Very Good(96)
Free Wi-Fi
Pool
$533+
Check availability
Natural Village #1,2,3 & 5 - San Juan
Natural Village #1,2,3 & 5
Santurce
7.2Good(278)
Parking
Free Wi-Fi
$119+
Check availability
The Oasis Retreat - Nassau
The Oasis Retreat
Nassau City
7.1Good(1024)
Parking
Free Wi-Fi
Pool
Pet friendly
$208+
Check availability
Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$0 - $291$291 - $580$580 - $869$869 - $1,158$1,158+ per night

Property type

ApartmentCondoHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

May

High season

February

Average price (weeknight)

$627

Average price (weekend night)

$565
Cheapest month to stay with an average 28% drop in price.
Most expensive month to stay with an average 11% 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 2 days.
  • Holiday rentals in Caribbean Islands are around 73% 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 Fort-de-France, with around 414 properties and an average price of $781. The most popular holiday rentals in Caribbean Islands among KAYAK users are Foyal Suites, Le Patio Foyalais, and Redoute Paradise.

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 $29. 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 $5,466.

  • 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 $23,424.

  • 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, boats, bungalows, cabins, campgrounds, chalets, condos, cottages, houses, homestays, houseboats, lodges, treehouses, villas, farm stays, towers, campsites, luxury tents, agritourism, castles, studios, barns and motorhomes.

  • 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.

Everything you need to know for your stay in Caribbean Islands

Not what you’re looking for? Find thousands of other hotels, flights, car hires and package deals with KAYAK.