Caribbean holiday rentals
We found 67,408 holiday rentals — enter your dates for availability
Popular cities in Caribbean
St. Thomas
St. Thomas
Providenciales
Providenciales
William's Town
William's Town
San Juan (and vicinity)
San Juan (and vicinity)Holiday rentals with weekly discounts - Caribbean
Showing deals for:29 May - 5 Jun
Image gallery for Beachfrot Paradise Villa for large groups prime location, daily cleanning & pool
9.09.0 out of 10, Wonderful, (12 reviews)
Wonderful
(12 reviews)
Beachfrot Paradise Villa for large groups prime location, daily cleanning & pool
Punta Cana
9% off
Price is S$18,298
S$18,298
for 7 nights, 1 villa
S$2,614 per night
includes taxes & fees
Image gallery for Amazing Ocean View Villa in Rincon, Puerto Rico
9.69.6 out of 10, Exceptional, (83 reviews)
Exceptional
(83 reviews)
Amazing Ocean View Villa in Rincon, Puerto Rico
Rincon
8% off
Price is S$6,881
S$6,881
for 7 nights, 1 villa
S$983 per night
includes taxes & fees
Image gallery for Casa Delfín by Luxe Haus™ – Butlered Villa, Staff, Pool, Golf Carts
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Casa Delfín by Luxe Haus™ – Butlered Villa, Staff, Pool, Golf Carts
La Romana
9% off
Price is S$14,505
S$14,505
for 7 nights, 1 villa
S$2,072 per night
includes taxes & fees
Image gallery for Romantic Oceanfront Beach Bungalow ON Beach PRIVATE w Club Resort Access &Tennis
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Romantic Oceanfront Beach Bungalow ON Beach PRIVATE w Club Resort Access &Tennis
south East Peninsula
8% off
Price is S$7,176
S$7,176
for 7 nights, 1 cottage
S$1,025 per night
includes taxes & fees
Image gallery for Guest House 2 bedrooms & 2 baths near Grace Bay Beach & Long Bay Beach.
9.69.6 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)
Guest House 2 bedrooms & 2 baths near Grace Bay Beach & Long Bay Beach.
Leeward Palms
9% off
Price is S$3,877
S$3,877
for 7 nights, 1 home
S$554 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$2,997
S$2,997
for 7 nights, 1 home
S$428 per night
includes taxes & fees
Image gallery for Cozy Villa 3 beds/2baths with pool and jacuzzi in SOSUA
1010 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Cozy Villa 3 beds/2baths with pool and jacuzzi in SOSUA
Sosúa
8% off
Price is S$1,729
S$1,729
for 7 nights, 1 villa
S$247 per night
includes taxes & fees
Image gallery for Cozy Villa in Casa De Campo with a Golf view, 3 mins away from beach.
1010 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Cozy Villa in Casa De Campo with a Golf view, 3 mins away from beach.
La Romana
9% off
Price is S$6,404
S$6,404
for 7 nights, 1 villa
S$915 per night
includes taxes & fees
Image gallery for Fantastic beach house on a secluded beach
9.69.6 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Fantastic beach house on a secluded beach
Aguada
12% off
Price is S$6,192
S$6,192
for 7 nights, 1 home
S$885 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, (32 reviews)
Exceptional
(32 reviews)
Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay
Tortola
8% off
Price is S$2,363
S$2,363
for 7 nights, 1 home
S$338 per night
includes taxes & fees
Image gallery for Charming 2-Bedroom House in Tranquil Staniel Cay near Thunderball Grotto
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Charming 2-Bedroom House in Tranquil Staniel Cay near Thunderball Grotto
Staniel Cay
13% off
Price is S$2,684
S$2,684
for 7 nights, 1 home
S$383 per night
includes taxes & fees
Image gallery for Villa Tasha Luxury Seafront Villa in Anguilla on the Caribbean sea AMAZING!
1010 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)
Villa Tasha Luxury Seafront Villa in Anguilla on the Caribbean sea AMAZING!
The Valley
7% off
Price is S$11,183
S$11,183
for 7 nights, 1 villa
S$1,598 per night
includes taxes & fees
Image gallery for Villa Gina Beachfront Villa
9.29.2 out of 10, Wonderful, (17 reviews)
Wonderful
(17 reviews)
Villa Gina Beachfront Villa
Cap estate
9% off
Price is S$4,877
S$4,877
for 7 nights, 1 villa
S$697 per night
includes taxes & fees
Image gallery for DISCOUNT, TURKS HAVEN VILLAS NEWLY BUILT LUXURY 1BR SUITE, STEPS TO THE BEACH!!
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
DISCOUNT, TURKS HAVEN VILLAS NEWLY BUILT LUXURY 1BR SUITE, STEPS TO THE BEACH!!
Long Bay Hills
8% off
Price is S$4,745
S$4,745
for 7 nights, 1 villa
S$678 per night
includes taxes & fees
Image gallery for Seas the Day TCI covered balcony, patio dining, gated entrance, on site security
1010 out of 10, Exceptional, (61 reviews)
Exceptional
(61 reviews)
Seas the Day TCI covered balcony, patio dining, gated entrance, on site security
Bluehills
6% off
Price is S$5,728
S$5,728
for 7 nights, 1 apartment
S$818 per night
includes taxes & fees
Image gallery for Isla Verde- Beach/Bar/Restaurants Near Airport For Same Day Booking Message me
9.29.2 out of 10, Wonderful, (42 reviews)
Wonderful
(42 reviews)
Isla Verde- Beach/Bar/Restaurants Near Airport For Same Day Booking Message me
Carolina
8% off
Price is S$1,611
S$1,611
for 7 nights, 1 home
S$230 per night
includes taxes & fees
Image gallery for 2-bedroom condo with WiFi, AC View of water from deck Pool
9.89.8 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
2-bedroom condo with WiFi, AC View of water from deck Pool
Anna's Retreat
9% off
Price is S$2,311
S$2,311
for 7 nights, 1 apartment
S$330 per night
includes taxes & fees
Image gallery for Designer House with a View
1010 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
Designer House with a View
Noord
8% off
Price is S$4,766
S$4,766
for 7 nights, 1 home
S$681 per night
includes taxes & fees
Image gallery for Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove
9.89.8 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)
Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove
South Sound
8% off
Price is S$1,834
S$1,834
for 7 nights, 1 apartment
S$262 per night
includes taxes & fees
Image gallery for Beachfront Family Stay · Courtyard View · AC All Rooms · Remodeled
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Beachfront Family Stay · Courtyard View · AC All Rooms · Remodeled
Luquillo
8% off
Price is S$1,568
S$1,568
for 7 nights, 1 apartment
S$224 per night
includes taxes & fees
Image gallery for Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go
8.88.8 out of 10, Excellent, (33 reviews)
Excellent
(33 reviews)
Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go
Carolina
8% off
Price is S$698
S$698
for 7 nights, 1 home
S$100 per night
includes taxes & fees
Image gallery for Beachfront Orient Bay 1‑BR Condo • Mont Vernon • Balcony • Pool • Fast Wi‑Fi
1010 out of 10, Exceptional, (43 reviews)
Exceptional
(43 reviews)
Beachfront Orient Bay 1‑BR Condo • Mont Vernon • Balcony • Pool • Fast Wi‑Fi
Cul de Sac
9% off
Price is S$1,103
S$1,103
for 7 nights, 1 apartment
S$158 per night
includes taxes & fees
Image gallery for Spacious 2 Bedroom steps from Eagle Beach at Aruba Breeze Condos
9.69.6 out of 10, Exceptional, (39 reviews)
Exceptional
(39 reviews)
Spacious 2 Bedroom steps from Eagle Beach at Aruba Breeze Condos
Noord
7% off
Price is S$2,311
S$2,311
for 7 nights, 1 apartment
S$330 per night
includes taxes & fees
Image gallery for Newly renovated! And What a view! Bed view is an ocean view superb location
9.89.8 out of 10, Exceptional, (46 reviews)
Exceptional
(46 reviews)
Newly renovated! And What a view! Bed view is an ocean view superb location
San Juan
8% off
Price is S$2,471
S$2,471
for 7 nights, 1 apartment
S$353 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Caribbean
Beautiful Private 10 Bedroom Beachfront Villa with hotel amenities
10 bedrooms · 10.5 bathrooms
1010 out of 10
Exceptional
exceptional
65 reviews
(65 reviews)
The Bohemian beach house
Sleeps 14 · 7 bedrooms · 8 bathrooms
1010 out of 10
Exceptional
exceptional
32 reviews
(32 reviews)
Magen's Bay Luxury Beachfront Villa // 30% off September 2026 Weeks
8 bedrooms · 9.5 bathrooms
1010 out of 10
Exceptional
exceptional
110 reviews
(110 reviews)
Great House Villa
2 bedrooms · 2 bathrooms
1010 out of 10
Exceptional
exceptional
80 reviews
(80 reviews)
Spectacular BEACHFRONT luxury Villa with private pool, Jacuzzi chef, full staff
11 bedrooms · 12.5 bathrooms
9.69.6 out of 10
Exceptional
exceptional
37 reviews
(37 reviews)
The Palms Punta Cana Villa
14 bedrooms · 16 bathrooms
1010 out of 10
Exceptional
exceptional
93 reviews
(93 reviews)