Caribbean holiday rentals
We found 69,564 holiday rentals — enter your dates for availability
Popular cities in Caribbean
Punta Cana
Punta Cana
San Juan (and vicinity)
San Juan (and vicinity)
Montego Bay
Montego Bay
St. Thomas
St. Thomas
Providenciales
ProvidencialesHoliday rentals with weekly discounts – Caribbean
Showing deals for:28 Aug - 4 Sept
Image gallery for The View has amazing vistas and an infinity pool
1010 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
The View has amazing vistas and an infinity pool
Gros Islet
8% off
Price is S$6,087
S$6,087
for 7 nights, 1 villa
S$870 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, (72 reviews)
Excellent
(72 reviews)
Paradise Haven in Palmas del Mar, a charming house for the perfect vacations!
Humacao
8% off
Price is S$3,030
S$3,030
for 7 nights, 1 home
S$433 per night
includes taxes & fees
Image gallery for Los Cayos Beach House
9.29.2 out of 10, Wonderful, (27 reviews)
Wonderful
(27 reviews)
Los Cayos Beach House
San Juan
8% off
Price is S$9,042
S$9,042
for 7 nights, 1 home
S$1,292 per night
includes taxes & fees
Image gallery for Villa Tropica - Near Grace Bay Beach - Newly Remodelled
9.89.8 out of 10, Exceptional, (136 reviews)
Exceptional
(136 reviews)
Villa Tropica - Near Grace Bay Beach - Newly Remodelled
Providenciales
7% off
Price is S$12,406
S$12,406
for 7 nights, 1 villa
S$1,772 per night
includes taxes & fees
Image gallery for Modern 1-bed studio in West Bay, with AC and private patio, short walk to beach!
9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Modern 1-bed studio in West Bay, with AC and private patio, short walk to beach!
West Bay
7% off
Price is S$1,468
S$1,468
for 7 nights, 1 cottage
S$210 per night
includes taxes & fees
Image gallery for Casa Delfín by Luxe Haus™ – Butlered Villa, Staff, Pool, Golf Carts
1010 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
Casa Delfín by Luxe Haus™ – Butlered Villa, Staff, Pool, Golf Carts
La Romana
10% off
Price is S$14,066
S$14,066
for 7 nights, 1 villa
S$2,009 per night
includes taxes & fees
Image gallery for Yes! This is your retreat, view of El Yunque, inside Coco Beach Resort.
1010 out of 10, Exceptional, (102 reviews)
Exceptional
(102 reviews)
Yes! This is your retreat, view of El Yunque, inside Coco Beach Resort.
Río Grande
9% off
Price is S$3,656
S$3,656
for 7 nights, 1 home
S$522 per night
includes taxes & fees
Image gallery for Exclusive 3 Bedroom Beachfront Villa, on the west cost.
9.09.0 out of 10, Wonderful, (46 reviews)
Wonderful
(46 reviews)
Exclusive 3 Bedroom Beachfront Villa, on the west cost.
Bridgetown
8% off
Price is S$4,605
S$4,605
for 7 nights, 1 villa
S$658 per night
includes taxes & fees
Image gallery for Azura: Modern Coastal Luxury Escape with Pool.
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Azura: Modern Coastal Luxury Escape with Pool.
Paynes Bay
9% off
Price is S$5,613
S$5,613
for 7 nights, 1 villa
S$802 per night
includes taxes & fees
Image gallery for Private Beachfront Luxury Villas with Dock & Heated Pools – Perfect for 10 Guests
9.69.6 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
Private Beachfront Luxury Villas with Dock & Heated Pools – Perfect for 10 Guests
Hartswell
8% off
Price is S$24,188
S$24,188
for 7 nights, 1 villa
S$3,455 per night
includes taxes & fees
Image gallery for A Beautiful Home Located Close To Beaches, Rain Forest, Golfing And Much More!
9.49.4 out of 10, Exceptional, (60 reviews)
Exceptional
(60 reviews)
A Beautiful Home Located Close To Beaches, Rain Forest, Golfing And Much More!
Luquillo
8% off
Price is S$2,753
S$2,753
for 7 nights, 1 home
S$393 per night
includes taxes & fees
Image gallery for Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool
9.29.2 out of 10, Wonderful, (23 reviews)
Wonderful
(23 reviews)
Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool
St. Barthelemy
8% off
Price is S$3,674
S$3,674
for 7 nights, 1 apartment
S$525 per night
includes taxes & fees
Image gallery for NEW LISTING! NEWLY UPDATED! Beachfront villa located at The Hideaways Resort
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
NEW LISTING! NEWLY UPDATED! Beachfront villa located at The Hideaways Resort
George Town
10% off
Price is S$3,249
S$3,249
for 7 nights, 1 villa
S$464 per night
includes taxes & fees
Image gallery for Luxury 6-bedroom villa in amazing view 6 min walking to the beach.
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Luxury 6-bedroom villa in amazing view 6 min walking to the beach.
Providenciales
8% off
Price is S$14,342
S$14,342
for 7 nights, 1 villa
S$2,049 per night
includes taxes & fees
Image gallery for Sunshine☀️House, with private water entry and high-speed Internet.
9.89.8 out of 10, Exceptional, (101 reviews)
Exceptional
(101 reviews)
Sunshine☀️House, with private water entry and high-speed Internet.
Rainbow Bay
8% off
Price is S$2,464
S$2,464
for 7 nights, 1 villa
S$352 per night
includes taxes & fees
Image gallery for SPECTACULAR NEW 4-BR, 3-BA on the BEST BEACH! - King Beds- LAST-MINUTE SPECIALS!
1010 out of 10, Exceptional, (61 reviews)
Exceptional
(61 reviews)
SPECTACULAR NEW 4-BR, 3-BA on the BEST BEACH! - King Beds- LAST-MINUTE SPECIALS!
Great Guana Cay
8% off
Price is S$8,486
S$8,486
for 7 nights, 1 home
S$1,212 per night
includes taxes & fees
Image gallery for Home with panoramic views with access to private beach!
1010 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
Home with panoramic views with access to private beach!
St. Thomas
8% off
Price is S$15,977
S$15,977
for 7 nights, 1 villa
S$2,282 per night
includes taxes & fees
Image gallery for Oceanfront Paradise in Exuma: Pool, Kayaks & Stunning Views Await You!
1010 out of 10, Exceptional, (143 reviews)
Exceptional
(143 reviews)
Oceanfront Paradise in Exuma: Pool, Kayaks & Stunning Views Await You!
Moss Town
8% off
Price is S$8,708
S$8,708
for 7 nights, 1 home
S$1,244 per night
includes taxes & fees
Image gallery for Cozy Corner w/ Private Pool, Pool Table, A/C, Wi-Fi, Laundry & Parking
9.69.6 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)
Cozy Corner w/ Private Pool, Pool Table, A/C, Wi-Fi, Laundry & Parking
Vega Baja
8% off
Price is S$1,871
S$1,871
for 7 nights, 1 home
S$267 per night
includes taxes & fees
Image gallery for Beautiful waterfront home w/ private dockage within HT Harbour
1010 out of 10, Exceptional, (48 reviews)
Exceptional
(48 reviews)
Beautiful waterfront home w/ private dockage within HT Harbour
Hope Town
25% off
Price is S$5,464
S$5,464
for 7 nights, 1 villa
S$781 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, (47 reviews)
Wonderful
(47 reviews)
Isla Verde- Beach/Bar/Restaurants Near Airport For Same Day Booking Message me
Carolina
8% off
Price is S$1,537
S$1,537
for 7 nights, 1 home
S$220 per night
includes taxes & fees
Image gallery for Spectacular beachfront villa. Great SNORKELING, kayaking, sunrise & sunset views
1010 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)
Spectacular beachfront villa. Great SNORKELING, kayaking, sunrise & sunset views
St. John
8% off
Price is S$6,214
S$6,214
for 7 nights, 1 villa
S$888 per night
includes taxes & fees
Image gallery for Seaview Paradise; located on Golf course!
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Seaview Paradise; located on Golf course!
Christiansted
8% off
Price is S$3,417
S$3,417
for 7 nights, 1 villa
S$488 per night
includes taxes & fees
Image gallery for Luxurious Villa " Sea La Vie" in Pelican Key
9.89.8 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Luxurious Villa " Sea La Vie" in Pelican Key
Simpson Bay
7% off
Price is S$5,014
S$5,014
for 7 nights, 1 villa
S$716 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
Sleeps 32 · 10 bedrooms · 10+ bathrooms
1010 out of 10
Exceptional
exceptional
66 reviews
(66 reviews)
Wyndham Grande Rio Mar Beach and Golf Resort
Sleeps 6 · 2 bedrooms · 2+ bathrooms
1010 out of 10
Exceptional
exceptional
18 reviews
(18 reviews)
Private Beachfront Luxury Estate with Infinity Pool & Concierge incl – Sleeps 16
Sleeps 16 · 6 bedrooms · 4+ bathrooms
1010 out of 10
Exceptional
exceptional
191 reviews
(191 reviews)
10BR Luxury Villa, Fully Staffed and w/ Chef-STSHA
Sleeps 20 · 10 bedrooms · 11 bathrooms
1010 out of 10
Exceptional
exceptional
3 reviews
(3 reviews)
Great House Villa
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptional
exceptional
86 reviews
(86 reviews)
Luxury Oceanfront Villa with Private Beach and Home Cinema
Sleeps 20 · 9 bedrooms · 8+ bathrooms
9.69.6 out of 10
Exceptional
exceptional
116 reviews
(116 reviews)