Caribbean Islands vacation rentals

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Latest Caribbean Islands vacation rental deals

MOST POPULARNassau
Vacation homes from C$ 75
Oranjestad
Vacation homes from C$ 48
Punta Cana
Vacation homes from C$ 17
Simpson Bay
Vacation homes from C$ 130

Best Caribbean Islands vacation rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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C$ 44 - C$ 222C$ 222 - C$ 401C$ 401 - C$ 579C$ 579 - C$ 756C$ 756+ per night

Property Types

ApartmentCondoHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Caribbean Islands

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Royal Terrace III (Prince) - Puerto Plata - Patio
Royal Terrace III (Prince)
Puerto Plata, Dominican Republic
9.8Wonderful(5)
Parking
Free Wi-Fi
C$ 47+
Check availability
Hibiscus - Le Gosier
Hibiscus
Le Gosier, Guadeloupe
7.0Good(9)
Parking
Free Wi-Fi
Pool
C$ 86+
Check availability
Greg House - Pointe-à-Pitre
Greg House
Pointe-à-Pitre, Guadeloupe
7.6Good(48)
Parking
Free Wi-Fi
C$ 101+
Check availability
Thijo Guadeloupe - Baie Mahault
Thijo Guadeloupe
Baie Mahault, Guadeloupe
9.3Wonderful(169)
Parking
Free Wi-Fi
Pool
C$ 108+
Check availability
Fleur d'Acacia - Les Trois-Îlets
Fleur d'Acacia
Les Trois-Îlets, Martinique
8.0Very good(143)
Parking
Free Wi-Fi
Pool
C$ 113+
Check availability
studio rose Karacoli - Les Trois-Îlets
studio rose Karacoli
Les Trois-Îlets, Martinique
9.3Wonderful(4)
Parking
Free Wi-Fi
Pool
C$ 120+
Check availability
Jadessie ' Centre ville - Downtown ' - Pointe-à-Pitre
Jadessie ' Centre ville - Downtown '
Pointe-à-Pitre, Guadeloupe
8.8Very good(84)
Parking
Free Wi-Fi
C$ 130+
Check availability
Foyal Suites - Fort-de-France - Bathroom
Foyal Suites
Fort-de-France, Martinique
8.0Very good(209)
Free Wi-Fi
C$ 157+
Check availability
Unit 1 Palazzo Rickets Drive Runaway Bay - Runaway Bay - Living room
Unit 1 Palazzo Rickets Drive Runaway Bay
Runaway Bay, Jamaica
8.3Very good(3)
Parking
Free Wi-Fi
C$ 173+
Check availability
Sandcastles Ochi In Ocho Rios Jamaica - Ocho Rios - Bedroom
Sandcastles Ochi In Ocho Rios Jamaica
Ocho Rios, Jamaica
8.2Very good(22)
Free Wi-Fi
Pool
C$ 180+
Check availability
Ri'Biero's Holiday Apartments - Crown Point - Pool
Ri'Biero's Holiday Apartments
Crown Point, Trinidad and Tobago
8.7Very good(42)
Free Wi-Fi
C$ 218+
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Mel-Bella Retreat - George Town - Living room
Mel-Bella Retreat
George Town, Cayman Islands
C$ 251+
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Penthouse On The Ridge - Ocho Rios - Living room
Penthouse On The Ridge
Ocho Rios, Jamaica
9.6Wonderful(44)
Free Wi-Fi
Pool
C$ 269+
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Standard Studio - George Town
Standard Studio
George Town, Cayman Islands
10Wonderful(1)
C$ 294+
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Aruba Villa with Pool, just 3 minutes driving from Aruba's best beaches - Noord - Bedroom
Aruba Villa with Pool, just 3 minutes driving from Aruba's best beaches
Noord, Aruba
9.3Wonderful(18)
C$ 352+
Check availability
Divi Village Villas - Oranjestad - Lobby
Divi Village Villas
Oranjestad, Aruba
10Wonderful(2)
Parking
Free Wi-Fi
Pool
C$ 915+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

October
March
C$ 232
C$ 216
Cheapest month to stay with an average 15% drop in price.
Most expensive month to stay with an average 29% 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$ 44, while the most expensive was C$ 525.
  • Vacation rentals in Caribbean Islands are around 69% 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 St. George's, with around 222 properties and an average price of C$ 85. The most popular vacation rentals in Caribbean Islands among KAYAK users are Bougainvillea Apartments, Reef View Pavilion Villas and Condos, and Hillview Apartments and Vehicle Rental.

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$ 39. Search here for similar prices

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

    In the last 72 hours, users have found Caribbean Islands vacation rentals for this weekend for as low as C$ 46 per night. 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$ 1,296.

  • 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$ 5,555.

  • 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, houses, homestays, villas, farm stays, lodges, cabins, cottages, vacation villages, luxury tents, boats, bungalows, chalets, houseboats, treehouses, barns, caravans, resorts, recreational vehicles, agritourism, 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 Beach Homes Punta Cana 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 home that can sleep 6 people or more by KAYAK users is A Pearl In Los Corales Playa Bavaro Punta Cana.

  • 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 6% 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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A Pearl In Los Corales Playa Bavaro Punta Cana - Punta Cana
A Pearl In Los Corales Playa Bavaro Punta Cana
Pueblo Bavaro
8.6Very good(15)
C$ 155+
Check availability
Numero Uno Beach Apartments - San Juan - Beach
Numero Uno Beach Apartments
Santurce
8.2Very good(38)
Free Wi-Fi
Pet friendly
C$ 392+
Check availability

Everything you need to know for your stay in Caribbean Islands

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