Caribbean holiday rentals
We found 67,759 holiday rentals — enter your dates for availability
Popular cities in Caribbean
St. Thomas
St. Thomas
Providenciales
Providenciales
William's Town
William's Town
George Town
George TownHoliday rentals with weekly discounts - Caribbean
Showing deals for:8 May - 15 May
Image gallery for Amazing luxury beach villas with private dock for 20 people! Large heated pools
9.89.8 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Amazing luxury beach villas with private dock for 20 people! Large heated pools
Exuma
8% off
Price is S$34,002
S$34,002
for 7 nights, 1 villa
S$4,857 per night
includes taxes & fees
Image gallery for VILLA BLUE LAGOON SXM ~ Ibiza Style in the Caribbean
9.89.8 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
VILLA BLUE LAGOON SXM ~ Ibiza Style in the Caribbean
Lowlands
8% off
Price is S$9,852
S$9,852
for 7 nights, 1 villa
S$1,407 per night
includes taxes & fees
Image gallery for Between luxury and authenticity. Beautiful sea view property, 100m from the beach.
1010 out of 10, Exceptional, (34 reviews)
Exceptional
(34 reviews)
Between luxury and authenticity. Beautiful sea view property, 100m from the beach.
Deshaies
18% off
Price is S$6,436
S$6,436
for 7 nights, 1 villa
S$919 per night
includes taxes & fees
Image gallery for Beautiful Aruba luxury villa La Casa Piu Bella
1010 out of 10, Exceptional, (61 reviews)
Exceptional
(61 reviews)
Beautiful Aruba luxury villa La Casa Piu Bella
Noord
9% off
Price is S$16,555
S$16,555
for 7 nights, 1 home
S$2,365 per night
includes taxes & fees
Image gallery for Casa Delfín by Luxe Haus™ – Butlered Villa, Staff, Pool, Golf Carts
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Casa Delfín by Luxe Haus™ – Butlered Villa, Staff, Pool, Golf Carts
La Romana
9% off
Price is S$14,193
S$14,193
for 7 nights, 1 villa
S$2,028 per night
includes taxes & fees
Image gallery for Rose Nest at the beach Puerto Rico
9.49.4 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Rose Nest at the beach Puerto Rico
Arecibo
8% off
Price is S$6,127
S$6,127
for 7 nights, 1 villa
S$875 per night
includes taxes & fees
Image gallery for Modern Oceanfront Home with Pool, Outdoor Showers and Private Tennis Court
9.89.8 out of 10, Exceptional, (117 reviews)
Exceptional
(117 reviews)
Modern Oceanfront Home with Pool, Outdoor Showers and Private Tennis Court
Micoud
9% off
Price is S$4,080
S$4,080
for 7 nights, 1 villa
S$583 per night
includes taxes & fees
Image gallery for OCEAN FRONT, 7M BEACH, PLANTATION VILLAGE #28
9.89.8 out of 10, Exceptional, (98 reviews)
Exceptional
(98 reviews)
OCEAN FRONT, 7M BEACH, PLANTATION VILLAGE #28
George Town
8% off
Price is S$4,700
S$4,700
for 7 nights, 1 apartment
S$671 per night
includes taxes & fees
Image gallery for Grace Bay Getaway: Beachwalk Compact Studio with shared Pool and Free Parking
9.69.6 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
Grace Bay Getaway: Beachwalk Compact Studio with shared Pool and Free Parking
The Bight Settlement
16% off
Price is S$2,495
S$2,495
for 7 nights, 1 apartment
S$356 per night
includes taxes & fees
Image gallery for El Yunque Rainforest Villa, Pool, Toro Trail, 5-Acre Hacienda, Fruit Trees
9.89.8 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
El Yunque Rainforest Villa, Pool, Toro Trail, 5-Acre Hacienda, Fruit Trees
Canóvanas
8% off
Price is S$4,221
S$4,221
for 7 nights, 1 villa
S$603 per night
includes taxes & fees
Image gallery for NEW 2BD/2.5 BATH near beach access and George town with PRIVATE POOL
9.49.4 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
NEW 2BD/2.5 BATH near beach access and George town with PRIVATE POOL
George Town
8% off
Price is S$4,312
S$4,312
for 7 nights, 1 home
S$616 per night
includes taxes & fees
Image gallery for Beachfrot Paradise Villa for large groups prime location, daily cleanning & pool
9.09.0 out of 10, Wonderful, (11 reviews)
Wonderful
(11 reviews)
Beachfrot Paradise Villa for large groups prime location, daily cleanning & pool
Punta Cana
9% off
Price is S$18,379
S$18,379
for 7 nights, 1 villa
S$2,626 per night
includes taxes & fees
Image gallery for Luxury 2 Bedroom Home With Private Dock and Pool On The North End
1010 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Luxury 2 Bedroom Home With Private Dock and Pool On The North End
Hope Town
9% off
Price is S$14,084
S$14,084
for 7 nights, 1 home
S$2,012 per night
includes taxes & fees
Image gallery for Beautiful villa West with pool- 5 minutes to Gracebay beach
9.89.8 out of 10, Exceptional, (75 reviews)
Exceptional
(75 reviews)
Beautiful villa West with pool- 5 minutes to Gracebay beach
Providenciales
8% off
Price is S$3,698
S$3,698
for 7 nights, 1 villa
S$528 per night
includes taxes & fees
Image gallery for Stunning Views, Peaceful Location, Large Pool & Minutes from Cruz Bay
9.89.8 out of 10, Exceptional, (71 reviews)
Exceptional
(71 reviews)
Stunning Views, Peaceful Location, Large Pool & Minutes from Cruz Bay
cruz bay
8% off
Price is S$9,611
S$9,611
for 7 nights, 1 villa
S$1,373 per night
includes taxes & fees
Image gallery for Le Diamant - Charming villa, private pool and tropical garden 300m from the sea
9.89.8 out of 10, Exceptional, (118 reviews)
Exceptional
(118 reviews)
Le Diamant - Charming villa, private pool and tropical garden 300m from the sea
Diamant
9% off
Price is S$1,757
S$1,757
for 7 nights, 1 home
S$251 per night
includes taxes & fees
Image gallery for Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay
1010 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay
Tortola
8% off
Price is S$2,362
S$2,362
for 7 nights, 1 home
S$337 per night
includes taxes & fees
Image gallery for Paradis - Luxurious Apartment with Ocean View and Balcony.
1010 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)
Paradis - Luxurious Apartment with Ocean View and Balcony.
San Juan
8% off
Price is S$2,440
S$2,440
for 7 nights, 1 apartment
S$349 per night
includes taxes & fees
Image gallery for Casa de Mer - On the Beach - Sun - Sand - Clear Bahamian Waters - Beachfront
9.89.8 out of 10, Exceptional, (74 reviews)
Exceptional
(74 reviews)
Casa de Mer - On the Beach - Sun - Sand - Clear Bahamian Waters - Beachfront
Nassau
9% off
Price is S$7,776
S$7,776
for 7 nights, 1 home
S$1,111 per night
includes taxes & fees
Image gallery for Luxurious Oceanfront Honeymoon Cottage - as seen on HGTV - Gated Subdivision
1010 out of 10, Exceptional, (198 reviews)
Exceptional
(198 reviews)
Luxurious Oceanfront Honeymoon Cottage - as seen on HGTV - Gated Subdivision
Christiansted
8% off
Price is S$2,612
S$2,612
for 7 nights, 1 cottage
S$373 per night
includes taxes & fees
Image gallery for Penthouse By The Beach
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Penthouse By The Beach
RIO GRANDE
6% off
Price is S$3,964
S$3,964
for 7 nights, 1 apartment
S$566 per night
includes taxes & fees
Image gallery for Fish Fever, Russell Island Bahamas
1010 out of 10, Exceptional, (53 reviews)
Exceptional
(53 reviews)
Fish Fever, Russell Island Bahamas
Russell Island / Spanish Wells
8% off
Price is S$2,477
S$2,477
for 7 nights, 1 home
S$354 per night
includes taxes & fees
Image gallery for Tropical modern villa with stunning sea views
1010 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Tropical modern villa with stunning sea views
Oyster Pond
8% off
Price is S$7,817
S$7,817
for 7 nights, 1 villa
S$1,117 per night
includes taxes & fees
Image gallery for Casa Mañana Vieques, Perfect for your large family or group!
9.89.8 out of 10, Exceptional, (49 reviews)
Exceptional
(49 reviews)
Casa Mañana Vieques, Perfect for your large family or group!
Vieques
8% off
Price is S$7,695
S$7,695
for 7 nights, 1 home
S$1,099 per night
includes taxes & fees
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Find the best place to stay - Caribbean
The Bohemian beach house
Sleeps 14 · 7 bedrooms · 8 bathrooms
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
Beautiful Private 10 Bedroom Beachfront Villa with hotel amenities
10 bedrooms · 10.5 bathrooms
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Magen's Bay Luxury Beachfront Villa // 20% off September 2026 Weeks
8 bedrooms · 9.5 bathrooms
1010 out of 10
Exceptionalexceptional
110 reviews(110 reviews)
Spectacular BEACHFRONT luxury Villa with private pool, Jacuzzi chef, full staff
11 bedrooms · 12.5 bathrooms
9.69.6 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Great House Villa
2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
79 reviews(79 reviews)
Caribbean Luxury Villa - House of Mermaids ✅Ocean View ✅Private Pool ✅Full Staff
5 bedrooms · 4.5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
142 reviews(142 reviews)