Caribbean holiday rentals
We found 68,075 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 Town
Holiday rentals with weekly discounts - Caribbean
Showing deals for:1 May - 8 May
Image gallery for Luxurious Tropical Villa close to the beach - Great cook fully staffed
1010 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)
Luxurious Tropical Villa close to the beach - Great cook fully staffed
La Romana
9% off
Price is S$14,242
S$14,242
for 7 nights, 1 villa
S$2,035 per night
includes taxes & fees
Image gallery for Ocean front luxury villa on Malmok Aruba
9.89.8 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
Ocean front luxury villa on Malmok Aruba
Aruba
8% off
Price is S$10,150
S$10,150
for 7 nights, 1 villa
S$1,450 per night
includes taxes & fees
Image gallery for 4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea
9.69.6 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea
Cole Bay
9% off
Price is S$5,807
S$5,807
for 7 nights, 1 villa
S$830 per night
includes taxes & fees
Image gallery for Sea Star – Private, Staffed, Luxury Jungle Compound – 10 Steps From The Beach
1010 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
Sea Star – Private, Staffed, Luxury Jungle Compound – 10 Steps From The Beach
Dunmore Town
5% off
Price is S$20,905
S$20,905
for 7 nights, 1 home
S$2,986 per night
includes taxes & fees
Image gallery for Carpe Diem, magnificent view of the marina
9.89.8 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Carpe Diem, magnificent view of the marina
OYSTER POND
5% off
Price is S$4,304
S$4,304
for 7 nights, 1 villa
S$615 per night
includes taxes & fees
Image gallery for C House Villa. Beautiful 5 bedroom house in Long Bay Hills, Providenciales
1010 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
C House Villa. Beautiful 5 bedroom house in Long Bay Hills, Providenciales
Long Bay Hills
8% off
Price is S$10,230
S$10,230
for 7 nights, 1 villa
S$1,461 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$2,475
S$2,475
for 7 nights, 1 apartment
S$354 per night
includes taxes & fees
Image gallery for Blue Serenity - Luxury, Oceanfront, Private Beach Access and Pool
1010 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
Blue Serenity - Luxury, Oceanfront, Private Beach Access and Pool
St. Thomas
8% off
Price is S$18,781
S$18,781
for 7 nights, 1 villa
S$2,683 per night
includes taxes & fees
Image gallery for Huge Villa! Walk to Beach, Casinos, and Restaurants. Private Pool & Swim-up Bar.
9.69.6 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)
Huge Villa! Walk to Beach, Casinos, and Restaurants. Private Pool & Swim-up Bar.
Bakval
8% off
Price is S$5,807
S$5,807
for 7 nights, 1 villa
S$830 per night
includes taxes & fees
Image gallery for Spectacular beachfront villa. Great SNORKELING, kayaking, sunrise & sunset views
1010 out of 10, Exceptional, (43 reviews)
Exceptional
(43 reviews)
Spectacular beachfront villa. Great SNORKELING, kayaking, sunrise & sunset views
St John
8% off
Price is S$7,286
S$7,286
for 7 nights, 1 villa
S$1,041 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$4,289
S$4,289
for 7 nights, 1 home
S$613 per night
includes taxes & fees
Image gallery for Pelican Paradise
1010 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
Pelican Paradise
Leeward Estates
8% off
Price is S$9,755
S$9,755
for 7 nights, 1 home
S$1,394 per night
includes taxes & fees
Image gallery for Beachfrot Paradise Villa for large groups prime location, daily cleanning & pool
9.29.2 out of 10, Wonderful, (10 reviews)
Wonderful
(10 reviews)
Beachfrot Paradise Villa for large groups prime location, daily cleanning & pool
Punta Cana
9% off
Price is S$17,810
S$17,810
for 7 nights, 1 villa
S$2,544 per night
includes taxes & fees
Image gallery for Lameshur Bay Glamping Site with AC
1010 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Lameshur Bay Glamping Site with AC
St John
8% off
Price is S$1,590
S$1,590
for 7 nights, 1 unit
S$227 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, (74 reviews)
Exceptional
(74 reviews)
Beautiful villa West with pool- 5 minutes to Gracebay beach
Providenciales
8% off
Price is S$3,659
S$3,659
for 7 nights, 1 villa
S$523 per night
includes taxes & fees
Image gallery for Paradise Haven in Palmas del Mar, a charming house for the perfect vacations!
8.68.6 out of 10, Excellent, (69 reviews)
Excellent
(69 reviews)
Paradise Haven in Palmas del Mar, a charming house for the perfect vacations!
Humacao
8% off
Price is S$2,954
S$2,954
for 7 nights, 1 home
S$422 per night
includes taxes & fees
Image gallery for Charming 2-Bedroom House in Tranquil Staniel Cay near Thunderball Grotto
1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Charming 2-Bedroom House in Tranquil Staniel Cay near Thunderball Grotto
Staniel Cay
13% off
Price is S$2,678
S$2,678
for 7 nights, 1 home
S$383 per night
includes taxes & fees
Image gallery for Cheerful Home with Gorgeous Ocean Views and Pool
9.69.6 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)
Cheerful Home with Gorgeous Ocean Views and Pool
Vieques,
9% off
Price is S$2,996
S$2,996
for 7 nights, 1 home
S$428 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$2,633
S$2,633
for 7 nights, 1 cottage
S$376 per night
includes taxes & fees
Image gallery for Paradis - Luxurious Apartment with Ocean View and Balcony.
1010 out of 10, Exceptional, (43 reviews)
Exceptional
(43 reviews)
Paradis - Luxurious Apartment with Ocean View and Balcony.
San Juan
8% off
Price is S$2,172
S$2,172
for 7 nights, 1 apartment
S$310 per night
includes taxes & fees
Image gallery for BEAUTIFUL 3 BEDROOM VILLA LOCATED DIRECTLY ON THE BEACH
1010 out of 10, Exceptional, (69 reviews)
Exceptional
(69 reviews)
BEAUTIFUL 3 BEDROOM VILLA LOCATED DIRECTLY ON THE BEACH
Grand Cayman
8% off
Price is S$3,635
S$3,635
for 7 nights, 1 villa
S$519 per night
includes taxes & fees
Image gallery for Oceanfront/Gated In-Ground Private Salt Water Pool/6 Bedroom; Luxury Paradise!
9.69.6 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)
Oceanfront/Gated In-Ground Private Salt Water Pool/6 Bedroom; Luxury Paradise!
Aguada
8% off
Price is S$14,455
S$14,455
for 7 nights, 1 home
S$2,065 per night
includes taxes & fees
Image gallery for Incredible Beach Front Villa with a Pool & Shipwreck Snorkeling!
1010 out of 10, Exceptional, (38 reviews)
Exceptional
(38 reviews)
Incredible Beach Front Villa with a Pool & Shipwreck Snorkeling!
George Town
9% off
Price is S$9,661
S$9,661
for 7 nights, 1 villa
S$1,380 per night
includes taxes & fees
Image gallery for studio nine feet in the water. New condo feet in water.
9.69.6 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
studio nine feet in the water. New condo feet in water.
Grand-Case
8% off
Price is S$1,630
S$1,630
for 7 nights, 1 apartment
S$233 per night
includes taxes & fees
Find spaces that suit your style
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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
31 reviews(31 reviews)
Beautiful Private 10 Bedroom Beachfront Villa with hotel amenities
Sleeps 32 · 10 bedrooms · 10+ bathrooms
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Magen's Bay Luxury Beachfront Villa // 20% off September 2026 Weeks
Sleeps 24 · 8 bedrooms · 9+ bathrooms
1010 out of 10
Exceptionalexceptional
110 reviews(110 reviews)
Spectacular BEACHFRONT luxury Villa with private pool, Jacuzzi chef, full staff
Sleeps 24 · 11 bedrooms · 12+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Caribbean Luxury Villa - House of Mermaids ✅Ocean View ✅Private Pool ✅Full Staff
Sleeps 12 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
142 reviews(142 reviews)
Villas Agua Dulce
Sleeps 12 · 5 bedrooms
9.89.8 out of 10
Exceptionalexceptional
18 reviews(18 reviews)