Caribbean Vacation Rentals - HolidayHomes base64Hash Caribbean Vacation Rentals - HolidayHomes

Caribbean Vacation Rentals

Browse 149,114 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

We use AI to generate the short summary in each offer below, check full description before booking.
House Whitby

Private Beachfront Luxury Estate pool with waterfall free concierge – Sleeps 16

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House Peterborg

Up to 50% off - October 2026 Reservation - Sand Dollar Estate

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Villa Chocolate Hole

OCEANFRONT, SWEEPING SUNRISE TO SUNSET VIEWS, CAN'T MISS AUG. LAST MINUTE DEALS

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Villa Leonards

AnaCapri Estate-Beautiful Caribbean Villa with pool and sea views

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House Green Cay

180° Sea Views, Luxurious Villa, Walk to secluded beach or beach bar

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House Zonicles

The Point House Luxury 5 bedroom Oceanfront Villa with Cliffside Pool, Kayaks

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Villa Chocolate Hole

Serenity Villa- Steps from Beach, Family Friendly

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Villa Les Anses-d'Arlet

Villa with terrace, garden & private pool

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Villa Chocolate Hole

Allesandra - Expansive Views - All A/C - 4 Bedroom villa. Pool-Spa!

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Villa Tortola

Villa with BBQ, terrace & private pool | Nature view

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Apartment Gros Islet

Rodney Bay Beach Home near EVERYTHING

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Villa Tortola

Twin Oceans - 4 bed/4 bath villa with pool and stunning views in west Tortola

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House Treasure Cay

Paradise Beach House a new 4 bedroom beachfront house with pool

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Villa Abra Grande

Charming villa with terrace, garden & private pool

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House Saint Barthélemy

House with garden & patio

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Top 15 most Recommended Vacation Rentals in the Caribbean

Discover your ideal Caribbean vacation rental with real-time comparisons of 149,114 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
Villa Les Trois-ÃŽlets
Villa ∙ 6 guests ∙ 3 bedrooms

Fully equipped big villa with garden, terrace & private pool | Sea view

Les Trois-ÃŽlets, Martinique
This villa in Les Trois-ÃŽlets accommodates 6 guests and features a private pool for relaxation and enjoyment.
from $20
per night
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Villa Sainte-Anne
Villa ∙ 6 guests ∙ 3 bedrooms

Villa with patio, private pool & grill

Sainte-Anne, Martinique
This charming villa in Sainte-Anne accommodates 6 guests and features a private pool for a relaxing getaway.
from $235
per night
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Apartment Telecable
Apartment ∙ 4 guests ∙ 1 bedroom

Rental apartment with fast internet, terrace & pool | Sea view

Telecable, Samana, Dominican Republic
This spacious apartment rental in Telecable accommodates 4 guests and features a balcony with stunning ocean views.
from $98
per night
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Bungalow Le Carbet
Bungalow ∙ 2 guests ∙ 1 bedroom

Wonderful bungalow with barbecue, patio & yard | Beach view | Close to the beach

Le Carbet, Arrondissement of Saint-Pierre, Martinique, Martinique
This charming bungalow in Le Carbet accommodates 2 guests and features beautiful ocean views.
from $38
per night
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Villa Grapetree
Villa ∙ 13 guests ∙ 5 bedrooms

Family-friendly big villa with private pool & grill | Sea view | Beach nearby | Suitable for remote work

Grapetree, East End, U.S. Virgin Islands
This spacious villa in Grapetree accommodates 13 guests and features a stunning ocean view.
from $200
per night
(2)
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Villa Saint Philip
Villa ∙ 2 guests ∙ 1 bedroom

Villa with garden, grill & private pool | Sea view

Saint Philip, Barbados
This cozy villa in Whitehaven accommodates 2 guests and features a private pool for a relaxing getaway.
from $152
per night
(3)
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Villa Petit Bourg
Villa ∙ 4 guests ∙ 2 bedrooms

Wonderful villa with garden, private pool & barbeque

Petit Bourg, Basse-Terre, Guadeloupe
This house rental in Petit Bourg accommodates 4 guests and features a refreshing pool for relaxation.
from $116
per night
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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 $127
per night
(23)
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Villa Water Island
Villa ∙ 27 guests ∙ 7 bedrooms

Child-friendly beautiful villa with private pool, yard & patio | Mountain view | Next to the beach | Good for workation

Water Island, St. Thomas, U.S. Virgin Islands
This spacious villa on Water Island accommodates 27 guests and features a private pool for relaxation and enjoyment.
from $1,524
per night
(78)
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