Caribbean Islands vacation rentals

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Latest Caribbean Islands vacation rental deals

MOST POPULARMontego Bay
Vacation homes from C$ 26
Nassau
Vacation homes from C$ 47
Oranjestad
Vacation homes from C$ 61
Punta Cana
Vacation homes from C$ 20
Providenciales
Vacation homes from C$ 177
Fort-de-France
Vacation homes from C$ 56

Best Caribbean Islands vacation rentals

Most recommended vacation rentals in Caribbean Islands

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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$ 219+
Check availability
Summerland Suites - Crown Point - Pool
Summerland Suites
Crown Point, Trinidad and Tobago
Free Wi-Fi
Pool
C$ 91+
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Foyal Suites - Fort-de-France - Bathroom
Foyal Suites
Fort-de-France, Martinique
8.2Very good(208)
Free Wi-Fi
C$ 161+
Check availability
Lesville Tobago - Crown Point - Building
Lesville Tobago
Crown Point, Trinidad and Tobago
Free Wi-Fi
C$ 83+
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Beach Living At Island Pine Villas (Blv) - George Town - Kitchen
Beach Living At Island Pine Villas (Blv)
George Town, Cayman Islands
10Wonderful(2)
Parking
Free Wi-Fi
Pool
C$ 679+
Check availability
Divi Village Villas - Oranjestad - Lobby
Divi Village Villas
Oranjestad, Aruba
10Wonderful(2)
Parking
Free Wi-Fi
Pool
C$ 983+
Check availability
I Heart Ja Serendipity Runaway Bay - Runaway Bay - Kitchen
I Heart Ja Serendipity Runaway Bay
Runaway Bay, Jamaica
Free Wi-Fi
C$ 197+
Check availability
Mood Haus By Dw - 70's Retro Stays - San Juan - Living room
Mood Haus By Dw - 70's Retro Stays
Santurce
8.3Very good(8)
Parking
Free Wi-Fi
Pet friendly
C$ 390+
Check availability
Incredible Beach Front Villa! - George Town - Beach
Incredible Beach Front Villa!
George Town, Cayman Islands
9.9Wonderful(14)
Parking
Free Wi-Fi
Pool
C$ 2,346+
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Laguna Del Mar - George Town - Living room
Laguna Del Mar
George Town, Cayman Islands
8.0Very good(3)
Parking
Free Wi-Fi
Pool
C$ 1,815+
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Lorna's Cottage - Crown Point - Kitchen
Lorna's Cottage
Crown Point, Trinidad and Tobago
8.2Very good(16)
Parking
Free Wi-Fi
C$ 145+
Check availability
Joli Studio Vue Sur Mer - Pointe-à-Pitre
Joli Studio Vue Sur Mer
Pointe-à-Pitre, Guadeloupe
8.2Very good(35)
Parking
Free Wi-Fi
C$ 125+
Check availability
Any's Appart - Fort-de-France
Any's Appart
Fort-de-France, Martinique
8.0Very good(37)
Parking
Free Wi-Fi
C$ 130+
Check availability
Transit Affaires - Loisirs - Pointe-à-Pitre
Transit Affaires - Loisirs
Pointe-à-Pitre, Guadeloupe
8.8Very good(28)
Free Wi-Fi
C$ 148+
Check availability
Sejour D Affaires Ou De Loisirs A Pointe A Pitre - Pointe-à-Pitre
Sejour D Affaires Ou De Loisirs A Pointe A Pitre
Pointe-à-Pitre, Guadeloupe
8.5Very good(45)
Free Wi-Fi
C$ 127+
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La bellevue - Les Trois-Îlets
La bellevue
Les Trois-Îlets, Martinique
9.5Wonderful(13)
Parking
Free Wi-Fi
C$ 116+
Check availability
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C$ 0 - C$ 428C$ 428 - C$ 855C$ 855 - C$ 1,283C$ 1,283 - C$ 1,709C$ 1,709+ per night

Property Types

ApartmentCondoCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

September

High season

February

Average price (weeknight)

C$ 377

Average price (weekend night)

C$ 377
Cheapest month to stay with an average 33% drop in price.
Most expensive month to stay with an average 76% 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$ 61, while the most expensive was C$ 300.
  • Vacation rentals in Caribbean Islands are around 108% 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 Puerto Plata, with around 796 properties and an average price of C$ 61. The most popular vacation rentals in Caribbean Islands among KAYAK users are Ecolodge Tubagua Puerto Plata, Costambar, and Casa Tropical.
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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$ 24. 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$ 852.

  • 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$ 3,653.

  • 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, towers, cabins, cottages, vacation villages, luxury tents, boats, bungalows, chalets, agritourism, houseboats, treehouses, barns, recreational vehicles, 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 The Oasis Retreat and Beach Homes Punta Cana.

  • 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 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 vacation home.

What Caribbean Islands vacation rental guests are talking about

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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
Punta Cana, Dominican Republic
8.6Very good(15)
Free Wi-Fi
C$ 156+
Check availability
Numero Uno Beach Apartments - San Juan
Numero Uno Beach Apartments
Santurce
8.0Very good(41)
Free Wi-Fi
Pet friendly
C$ 488+
Check availability

Popular topics

Everything you need to know for your stay in Caribbean Islands

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