Caribbean holiday rentals
We found 67,853 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 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$34,039
S$34,039
for 7 nights, 1 villa
S$4,863 per night
includes taxes & fees
Image gallery for Luxury beachfront villa with dock and a private large heated pool. For 10 people
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Luxury beachfront villa with dock and a private large heated pool. For 10 people
George Town
8% off
Price is S$23,760
S$23,760
for 7 nights, 1 villa
S$3,394 per night
includes taxes & fees
Image gallery for Casa Azul welcomes you to a stunning ocean view condo steps away from the beach
1010 out of 10, Exceptional, (37 reviews)
Exceptional
(37 reviews)
Casa Azul welcomes you to a stunning ocean view condo steps away from the beach
Bailey Town
8% off
Price is S$3,547
S$3,547
for 7 nights, 1 apartment
S$507 per night
includes taxes & fees
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$14,340
S$14,340
for 7 nights, 1 villa
S$2,049 per night
includes taxes & fees
Image gallery for Fully staffed. private, Beachfront villa with a pool in Negril, Jamaica
1010 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)
Fully staffed. private, Beachfront villa with a pool in Negril, Jamaica
Negril
8% off
Price is S$25,054
S$25,054
for 7 nights, 1 villa
S$3,579 per night
includes taxes & fees
Image gallery for THE BEACH HOUSE YOU HAVE BEEN DREAMING ABOUT!
1010 out of 10, Exceptional, (47 reviews)
Exceptional
(47 reviews)
THE BEACH HOUSE YOU HAVE BEEN DREAMING ABOUT!
Treasure Beach
18% off
Price is S$5,611
S$5,611
for 7 nights, 1 villa
S$802 per night
includes taxes & fees
Image gallery for The View has amazing vistas and an infinity pool
1010 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)
The View has amazing vistas and an infinity pool
Cap Estate
8% off
Price is S$6,123
S$6,123
for 7 nights, 1 villa
S$875 per night
includes taxes & fees
Image gallery for VILLA SERENE—2 Bed, 2.5 Bath Villa with Beach Access just steps to Sapodilla Bay
9.89.8 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)
VILLA SERENE—2 Bed, 2.5 Bath Villa with Beach Access just steps to Sapodilla Bay
Providenciales
8% off
Price is S$5,596
S$5,596
for 7 nights, 1 villa
S$799 per night
includes taxes & fees
Image gallery for Colorful Caribbean Cottage • King Bed, Pool, Lush Garden Views
1010 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
Colorful Caribbean Cottage • King Bed, Pool, Lush Garden Views
st. john
8% off
Price is S$3,529
S$3,529
for 7 nights, 1 cottage
S$504 per night
includes taxes & fees
Image gallery for Private Seven Mile Beach Club with Roof Terrace, Amazing Pool Pavilion
1010 out of 10, Exceptional, (56 reviews)
Exceptional
(56 reviews)
Private Seven Mile Beach Club with Roof Terrace, Amazing Pool Pavilion
West Bay
5% off
Price is S$11,120
S$11,120
for 7 nights, 1 apartment
S$1,589 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$10,300
S$10,300
for 7 nights, 1 villa
S$1,471 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$4,289
S$4,289
for 7 nights, 1 villa
S$613 per night
includes taxes & fees
Image gallery for Beach Front Resort Villa ( 1 bedroom, sleeps 4) closest to hotel OV3
9.29.2 out of 10, Wonderful, (53 reviews)
Wonderful
(53 reviews)
Beach Front Resort Villa ( 1 bedroom, sleeps 4) closest to hotel OV3
Río Grande
12% off
Price is S$2,991
S$2,991
for 7 nights, 1 apartment
S$427 per night
includes taxes & fees
Image gallery for Paradise Haven in Palmas del Mar, a charming house for the perfect vacations!
8.88.8 out of 10, Excellent, (68 reviews)
Excellent
(68 reviews)
Paradise Haven in Palmas del Mar, a charming house for the perfect vacations!
Humacao
8% off
Price is S$2,974
S$2,974
for 7 nights, 1 home
S$425 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, (29 reviews)
Exceptional
(29 reviews)
Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay
Tortola
8% off
Price is S$2,364
S$2,364
for 7 nights, 1 home
S$338 per night
includes taxes & fees
Image gallery for The premier beachfront villa on Playa Las Ballenas, Las Terrenas, Dominican Rep.
9.89.8 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
The premier beachfront villa on Playa Las Ballenas, Las Terrenas, Dominican Rep.
Las Terrenas
9% off
Price is S$13,657
S$13,657
for 7 nights, 1 villa
S$1,951 per night
includes taxes & fees
Image gallery for Apartment with a million dollar view and a wrap-around balcony with beach access
9.29.2 out of 10, Wonderful, (29 reviews)
Wonderful
(29 reviews)
Apartment with a million dollar view and a wrap-around balcony with beach access
Castries
8% off
Price is S$2,077
S$2,077
for 7 nights, 1 apartment
S$297 per night
includes taxes & fees
Image gallery for Sapphire Beach Resort Rental
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Sapphire Beach Resort Rental
St Thomas
20% off
Price is S$5,306
S$5,306
for 7 nights, 1 apartment
S$758 per night
includes taxes & fees
Image gallery for Vacation Home with Private Pool in Tropical Setting on East End, St. Croix.
1010 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)
Vacation Home with Private Pool in Tropical Setting on East End, St. Croix.
christiansted
8% off
Price is S$3,858
S$3,858
for 7 nights, 1 home
S$551 per night
includes taxes & fees
Image gallery for One of Puerto Rico’s Most Stunning 5 bedroom Oceanview Villas with Pool & Slide
1010 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
One of Puerto Rico’s Most Stunning 5 bedroom Oceanview Villas with Pool & Slide
Fajardo
13% off
Price is S$13,968
S$13,968
for 7 nights, 1 home
S$1,995 per night
includes taxes & fees
Image gallery for New listing! Spacious 4-bedroom, water-front house in Las Picuas, Río Grande.
1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
New listing! Spacious 4-bedroom, water-front house in Las Picuas, Río Grande.
Río Grande
8% off
Price is S$8,038
S$8,038
for 7 nights, 1 home
S$1,148 per night
includes taxes & fees
Image gallery for 2 minute walk to Grace Bay Beach - Modern, Immaculate 4 Bedroom, 4 Full Bath
1010 out of 10, Exceptional, (54 reviews)
Exceptional
(54 reviews)
2 minute walk to Grace Bay Beach - Modern, Immaculate 4 Bedroom, 4 Full Bath
The Bight Settlement
8% off
Price is S$11,461
S$11,461
for 7 nights, 1 villa
S$1,637 per night
includes taxes & fees
Image gallery for The Villa Michelle • Luxury • Heated Pool • Generator
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
The Villa Michelle • Luxury • Heated Pool • Generator
St Thomas
7% off
Price is S$9,816
S$9,816
for 7 nights, 1 villa
S$1,402 per night
includes taxes & fees
Image gallery for Villa Angelina with Amazing Panoramic Views. Enjoy the quiet at Oyster Pond
9.69.6 out of 10, Exceptional, (58 reviews)
Exceptional
(58 reviews)
Villa Angelina with Amazing Panoramic Views. Enjoy the quiet at Oyster Pond
Oyster Pond
7% off
Price is S$2,987
S$2,987
for 7 nights, 1 villa
S$427 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
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
141 reviews(141 reviews)
Villas Agua Dulce
Sleeps 12 · 5 bedrooms
9.89.8 out of 10
Exceptionalexceptional
18 reviews(18 reviews)