Caribbean Vacation Rentals - HolidayHomes base64Hash Caribbean Vacation Rentals - HolidayHomes

Caribbean Vacation Rentals

Browse 147,823 available vacation homes and compared across 192 trusted partners

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Top-Rated Vacation rentals in the Caribbean

Book the highest-rated Caribbean vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Villa La Vallee
Private Gated Ocean Front Villa Pool&Tide Pool Cane Bay Beach Wifi Wedding Venue
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Condo George Town
Prime Residence 6 on 7 Mile Beach, High-End Ground Floor Beachfront Condo
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House La Vallee
Premier Partner: Close to beach! Refreshing pool! Beautiful Ocean Views!
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Villa Nassau
OCEAN PARADISE, 35 Steps INTO SEA! PRIVATE POOL, BEACH-10min Walk, Near ATLANTIS!
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Villa Hellene
Modern Oceanfront Home with Pool, Outdoor Showers and Private Tennis Court
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House Rum Point
SEA SEA SEA Beachfront HomeAway from Home in Tranquil Community of Rum Point
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House North Palmetto Point
BEACHFRONT HOME AND POOL, 4BR/4 BATHROOMS
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Condo West Bay
Cayman Islands Diver and Snorkeler Paradise with Direct Oceanfront Access
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Apartment Rendezvous And Ditleff
Amazing views, great breeze, huge infinity pool & hot tub, 2-5 BR, solar powered
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Villa Chocolate Hole
Oceanport Villa: Great location, stunning views with pool and spa
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Villa Leonards
AnaCapri Estate-Beautiful Caribbean Villa with pool and sea views
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Villa Whitehall
Private Historic Nevis Estate Pool, Atlantic Views & Sleeps 7
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Villa Anguilla
Villa with yard, private pool & patio
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House Saint James
Beautiful spacious holiday home private shared pool with neighbour nr Sandy Lane
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House Green Cay
180° Sea Views, Luxurious Villa, Walk to secluded beach or beach bar
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Top 15 most Recommended Vacation Rentals in the Caribbean

Discover your ideal Caribbean vacation rental with real-time comparisons of 147,823 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Cayman Islands
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped pleasant vacation home with patio

Cayman Islands
This house rental in the Cayman Islands accommodates 10 guests and features beach access for a relaxing getaway.
from $585
per night
(20)
View deal
Condo Golden Rock
Condo ∙ 10 guests ∙ 5 bedrooms

Fully equipped nice condo with pool & patio | Beach nearby

Golden Rock, Sion Farm, U.S. Virgin Islands
This spacious 10-person condo in Golden Rock features a modern kitchen and access to a refreshing pool.
from $460
per night
(19)
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House Water Island
House ∙ 5 guests ∙ 2 bedrooms

Vacation home with patio & private pool

Water Island, St. Thomas, U.S. Virgin Islands
This charming cabin on Water Island accommodates 5 guests and features a family-friendly kitchen for convenient meal prep.
from $102
per night
(21)
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Villa La Perla
Villa ∙ 20 guests ∙ 8 bedrooms

Villa with private pool, BBQ & patio | Next to Castillo San Cristóbal | Mountain view

La Perla, Old San Juan, Puerto Rico
This spacious 20-capacity villa in La Perla features a private pool and offers a perfect retreat for families and friends.
from $801
per night
(17)
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House East End
House ∙ 11 guests ∙ 4 bedrooms

Fully equipped spacious house with terrace, barbecue & private pool

East End, Cayman Islands
This house rental in Gun Bay accommodates 8 guests and features a private pool for relaxation and enjoyment.
from $746
per night
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Condo Golden Rock
Condo ∙ 8 guests ∙ 4 bedrooms

Child-friendly nice condo with pool, barbecue & patio | Beach nearby | Good for workation

Golden Rock, Sion Farm, U.S. Virgin Islands
This spacious condo in Golden Rock accommodates 8 guests and features a beautiful balcony with stunning views.
from $381
per night
(32)
View deal
House Nassau
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with pool, terrace & barbeque

Nassau, New Providence, The Bahamas
This house rental in Nassau accommodates 10 guests and features a relaxing pool for your enjoyment.
from $390
per night
(21)
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House Tabor And Harmony
House ∙ 12 guests ∙ 5 bedrooms

Child-friendly big house with private pool, terrace & grill | Nature view | Pet-friendly

Tabor And Harmony, East End, U.S. Virgin Islands
This spacious house rental in Tabor And Harmony accommodates 12 guests and features a private pool for relaxation and fun.
from $960
per night
(208)
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House West Bay
House ∙ 9 guests ∙ 4 bedrooms

Vacation home with private pool, barbeque & garden

West Bay, Cayman Islands
This house rental in West Bay accommodates 9 guests and features a private pool for your enjoyment.
from $607
per night
(6)
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