Caribbean Islands vacation rentals

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Latest Caribbean Islands vacation rental deals

MOST POPULARNassau
Vacation homes from C$ 40
Oranjestad
Vacation homes from C$ 67
Punta Cana
Vacation homes from C$ 19
Bridgetown
Vacation homes from C$ 57

Best Caribbean Islands vacation rentals

Apartamentos Melya cerca de la Playa Caleta - La Romana - Balcony
Apartamentos Melya cerca de la Playa Caleta
La Romana, Dominican Republic
8.1Very good(119)
Apartment
Free Wi-Fi
Pool
Pet friendly
C$ 58+
Check availability
Apartment in the center of Pointe-A-Pitre - Pointe-à-Pitre - Living room
Apartment in the center of Pointe-A-Pitre
Pointe-à-Pitre, Guadeloupe
Apartment
C$ 86+
Check availability
Furnished seasonal rental (studio) - Pointe-à-Pitre - Bedroom
Furnished seasonal rental (studio)
Pointe-à-Pitre, Guadeloupe
Apartment
C$ 91+
Check availability
Comfortable apartment - Pointe-à-Pitre - Bathroom
Comfortable apartment
Pointe-à-Pitre, Guadeloupe
Apartment
C$ 96+
Check availability
Mountain and Sea view Stay - Sandy Point Town - Bedroom
Mountain and Sea view Stay
Sandy Point Town, Saint Kitts and Nevis
8.8Very good(4)
House
Free Wi-Fi
C$ 103+
Check availability
Arnaud-Michel - Pointe-à-Pitre
Arnaud-Michel
Pointe-à-Pitre, Guadeloupe
7.4Good(27)
Apartment
Free Wi-Fi
C$ 121+
Check availability
A spacious and warm F5 for your vacation or your stay! - Fort-de-France - Living room
A spacious and warm F5 for your vacation or your stay!
Fort-de-France, Martinique
House
C$ 142+
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Barbados Chi Guest House - Bridgetown - Patio
Barbados Chi Guest House
Bridgetown, Barbados
7.3Good(3)
Apartment
Free Wi-Fi
C$ 151+
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Sandcastles Ochi In Ocho Rios Jamaica - Ocho Rios - Bedroom
Sandcastles Ochi In Ocho Rios Jamaica
Ocho Rios, Jamaica
8.3Very good(22)
Condo
Free Wi-Fi
C$ 179+
Check availability
Castle by the Shore - Ocho Rios - Beach
Castle by the Shore
Ocho Rios, Jamaica
9.3Wonderful(52)
Condo
Parking
Free Wi-Fi
Pool
C$ 190+
Check availability
Luxury Furnished Rental - Fort-de-France - Front desk
Luxury Furnished Rental
Fort-de-France, Martinique
Apartment
Free Wi-Fi
C$ 190+
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Gorgeous hideout, close to tourist attractions in Jamaica - Runaway Bay - Pool
Gorgeous hideout, close to tourist attractions in Jamaica
Runaway Bay, Jamaica
10Wonderful(5)
Apartment
Parking
Free Wi-Fi
Pool
C$ 294+
Check availability
Aruba Beach Villas - Oranjestad - Beach
Aruba Beach Villas
Oranjestad, Aruba
7.9Good(366)
Holiday Park
Parking
Free Wi-Fi
Pool
C$ 297+
Check availability
1-bedroom apartment in Frigatebay - Frigate Bay - Living room
1-bedroom apartment in Frigatebay
Frigate Bay, Saint Kitts and Nevis
Apartment
C$ 418+
Check availability
Marriotts St Kitts Beach Club - 2 Bedroom - Basseterre - Pool
Marriotts St Kitts Beach Club - 2 Bedroom
Basseterre, Saint Kitts and Nevis
Condo
C$ 1,306+
Check availability
Spacious Two-Bedroom Townhouse in Gated Community - 5 min drive to the beach! - George Town - Pool
Spacious Two-Bedroom Townhouse in Gated Community - 5 min drive to the beach!
George Town, Cayman Islands
10Wonderful(1)
House
Free Wi-Fi
C$ 1,834+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

July
February
C$ 289
C$ 340
Cheapest month to stay with an average 29% drop in price.
Most expensive month to stay with an average 17% 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 8 days.
  • The cheapest Caribbean Islands vacation rental found on KAYAK in the last 2 weeks was C$ 52, while the most expensive was C$ 750.
  • Vacation rentals in Caribbean Islands are around 70% 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 Las Terrenas, with around 746 properties and an average price of C$ 28. The most popular vacation rentals in Caribbean Islands among KAYAK users are Residencial Don Cesar (Apt. Penthouse), Villa Kate, and Secure 4-pers apartment close to the beach.

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 C$ 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 C$ 1,477.

  • 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 C$ 6,331.

  • 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, cabins, cottages, vacation villages, luxury tents, bungalows, chalets, houseboats, treehouses, barns, caravans, hotels, resorts, 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 J&G Villa Hotel and Viking Hill Oceanfront Hostel & Resort.

  • 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 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 vacation home.

What Caribbean Islands vacation rental guests are talking about

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Vacation 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
C$ 466+
Check availability

Everything you need to know for your stay in Caribbean Islands