Caribbean Islands holiday rentals

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Best Caribbean Islands holiday rentals

Story Villa 2 Bedrooms with Mountain & Ocean View - Canaries - Living room
Story Villa 2 Bedrooms with Mountain & Ocean View
Canaries, Saint Lucia
10Wonderful(5)
Villa
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€109+
Check availability
Mar Del Norte - San Juan - Room amenity
Mar Del Norte
San Juan, Puerto Rico
8.9Very Good(1425)
Apartment
Parking
Free Wi-Fi
Air conditioning
€119+
Check availability
Maho Beach House - Elegant 1 Bedroom, Beach Level - Simpson Bay - Kitchen
Maho Beach House - Elegant 1 Bedroom, Beach Level
Simpson Bay, St. Maarten
7.7Good(5)
Apartment
Free Wi-Fi
Pet friendly
Air conditioning
€420+
Check availability
Montego Bay Club Apartments - Montego Bay - Pool
Montego Bay Club Apartments
Ocean Front
7.3Good(262)
Apartment
Parking
Free Wi-Fi
Pool
Air conditioning
€148+
Check availability
1 bedroom apt with pool in Simpson Bay - Cole Bay - Pool
1 bedroom apt with pool in Simpson Bay
Cole Bay, St. Maarten
9.1Wonderful(6)
Apartment
Parking
Free Wi-Fi
Air conditioning
€205+
Check availability
Simpson Bay Beach Modern Apartment. Roof Deck Ocean Views Wifi Satellite Tv. - Simpson Bay - Beach
Simpson Bay Beach Modern Apartment. Roof Deck Ocean Views Wifi Satellite Tv.
Simpson Bay, St. Maarten
9.6Wonderful(26)
Apartment
Free Wi-Fi
Air conditioning
€199+
Check availability
Puerta Al-Mar Villa - Simpson Bay - Pool
Puerta Al-Mar Villa
Simpson Bay, St. Maarten
Villa
Parking
Free Wi-Fi
Air conditioning
€847+
Check availability
Curacasitas - Willemstad
Curacasitas
Willemstad, Curaçao
8.8Very Good(9)
Apartment
Parking
Free Wi-Fi
Air conditioning
€50+
Check availability
Maho Beach House - Grand Studio - Oceanview Suite - Simpson Bay
Maho Beach House - Grand Studio - Oceanview Suite
Simpson Bay, St. Maarten
6.7Okay(9)
Apartment
Free Wi-Fi
Pool
Pet friendly
Air conditioning
€381+
Check availability
Central Oaklands Kingston Apt - Kingston
Central Oaklands Kingston Apt
Kingston, Jamaica
9.0Wonderful(11)
Apartment
Parking
Free Wi-Fi
Air conditioning
€131+
Check availability
Latitude Adjustment - San Juan
Latitude Adjustment
San Juan, Puerto Rico
9.2Wonderful(116)
Apartment
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€148+
Check availability
Morea Sxm - Simpson Bay
Morea Sxm
Simpson Bay, St. Maarten
Apartment
Free Wi-Fi
Air conditioning
€382+
Check availability
Cozy apartment - Kingston
Cozy apartment
Kingston, Jamaica
7.1Good(13)
Apartment
Parking
Free Wi-Fi
Air conditioning
€58+
Check availability
Willemstad Punda - Willemstad
Willemstad Punda
Willemstad, Curaçao
6.8Okay(13)
Apartment
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€58+
Check availability
Serenity Seaview Suite - Castries
Serenity Seaview Suite
Castries, Saint Lucia
9.6Wonderful(69)
Apartment
Parking
Free Wi-Fi
Air conditioning
€90+
Check availability
Vista Mariposa Apartment - Willemstad
Vista Mariposa Apartment
Willemstad, Curaçao
9.6Wonderful(5)
Apartment
Parking
Free Wi-Fi
Air conditioning
€77+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

September
February
€224
€255
Cheapest month to stay with an average 48% drop in price.
Most expensive month to stay with an average 5% 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 7 days.
  • The cheapest Caribbean Islands holiday rental found on KAYAK in the last 2 weeks was €24, while the most expensive was €131.
  • Holiday rentals in Caribbean Islands are around 96% cheaper than hotels on average. Search here to compare prices for all accommodation types in Caribbean Islands.

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 €20. 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, villas, resorts, cottages, cabins, campsites, luxury tents, bungalows, chalets, houseboats, treehouses, barns, caravans, hotels, boats, agritourism, bed & breakfasts, studios and castles.

  • 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 Ocean Spray Apartments.

  • 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 5% 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 holiday home.

What Caribbean Islands holiday rental guests are talking about

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Popular topics

Holiday rentals by topic

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Numero Uno Beach Apartments - San Juan - Beach
Numero Uno Beach Apartments
Santurce
8.8Very Good(39)
Apartment
Free Wi-Fi
Pet friendly
Air conditioning
€292+
Check availability

Everything you need to know for your stay in Caribbean Islands

Complete your trip to Caribbean Islands

Flights to Caribbean Islands
Car hire in Caribbean Islands