Caribbean holiday rentals
We found 67,328 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:17 Apr - 24 Apr
Image gallery for Private Seven Mile Beach Club with Roof Terrace, Amazing Pool Pavilion
1010 out of 10, Exceptional, (55 reviews)
Exceptional
(55 reviews)
Private Seven Mile Beach Club with Roof Terrace, Amazing Pool Pavilion
West Bay
5% off
Price is S$12,278
S$12,278
for 7 nights, 1 apartment
S$1,754 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$5,166
S$5,166
for 7 nights, 1 villa
S$738 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, (49 reviews)
Exceptional
(49 reviews)
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea
Cole Bay
9% off
Price is S$6,846
S$6,846
for 7 nights, 1 villa
S$978 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$5,705
S$5,705
for 7 nights, 1 villa
S$815 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, (23 reviews)
Exceptional
(23 reviews)
Grace Bay Getaway: Beachwalk Compact Studio with shared Pool and Free Parking
The Bight Settlement
16% off
Price is S$2,506
S$2,506
for 7 nights, 1 apartment
S$358 per night
includes taxes & fees
Image gallery for Sandy Shoes, Russell Island , Bahamas
1010 out of 10, Exceptional, (85 reviews)
Exceptional
(85 reviews)
Sandy Shoes, Russell Island , Bahamas
Spanish Wells
9% off
Price is S$4,023
S$4,023
for 7 nights, 1 home
S$575 per night
includes taxes & fees
Image gallery for Home with panoramic views with access to private beach!
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Home with panoramic views with access to private beach!
St Thomas
8% off
Price is S$16,076
S$16,076
for 7 nights, 1 villa
S$2,297 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$6,888
S$6,888
for 7 nights, 1 villa
S$984 per night
includes taxes & fees
Image gallery for Pelican Paradise
1010 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
Pelican Paradise
Leeward Estates
8% off
Price is S$10,095
S$10,095
for 7 nights, 1 home
S$1,442 per night
includes taxes & fees
Image gallery for NEW! Amazing view, two king bedroom w/ensuite bathrooms. Private heated pool.
9.89.8 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
NEW! Amazing view, two king bedroom w/ensuite bathrooms. Private heated pool.
George Town
8% off
Price is S$6,487
S$6,487
for 7 nights, 1 home
S$927 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$17,790
S$17,790
for 7 nights, 1 villa
S$2,541 per night
includes taxes & fees
Image gallery for Summer Special Cayman Reef Resort Oceanfront 1-Bed 1-Bath Condo. On 7-Mile Beach
9.89.8 out of 10, Exceptional, (138 reviews)
Exceptional
(138 reviews)
Summer Special Cayman Reef Resort Oceanfront 1-Bed 1-Bath Condo. On 7-Mile Beach
George Town
7% off
Price is S$4,260
S$4,260
for 7 nights, 1 apartment
S$609 per night
includes taxes & fees
Image gallery for The peace and tranquility of this cottage Works Wonders on the soul....
1010 out of 10, Exceptional, (71 reviews)
Exceptional
(71 reviews)
The peace and tranquility of this cottage Works Wonders on the soul....
Grand Cayman
8% off
Price is S$7,835
S$7,835
for 7 nights, 1 home
S$1,119 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$3,518
S$3,518
for 7 nights, 1 apartment
S$503 per night
includes taxes & fees
Image gallery for Newly Updated! Private Beach Views, Luxury Villa Milagro! Villa 2
1010 out of 10, Exceptional, (80 reviews)
Exceptional
(80 reviews)
Newly Updated! Private Beach Views, Luxury Villa Milagro! Villa 2
Charlotte Amalie
7% off
Price is S$2,351
S$2,351
for 7 nights, 1 villa
S$336 per night
includes taxes & fees
Image gallery for Paradis - Luxurious Apartment with Ocean View and Balcony.
1010 out of 10, Exceptional, (42 reviews)
Exceptional
(42 reviews)
Paradis - Luxurious Apartment with Ocean View and Balcony.
San Juan
8% off
Price is S$2,275
S$2,275
for 7 nights, 1 apartment
S$325 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$7,804
S$7,804
for 7 nights, 1 home
S$1,115 per night
includes taxes & fees
Image gallery for Relax in coastal luxury - renovated oceanfront condo Kaibo phase 2 - B13
1010 out of 10, Exceptional, (102 reviews)
Exceptional
(102 reviews)
Relax in coastal luxury - renovated oceanfront condo Kaibo phase 2 - B13
Grand Cayman
8% off
Price is S$4,144
S$4,144
for 7 nights, 1 apartment
S$592 per night
includes taxes & fees
Image gallery for Fantastic beach house on a secluded beach
9.49.4 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)
Fantastic beach house on a secluded beach
Aguada
12% off
Price is S$6,299
S$6,299
for 7 nights, 1 home
S$900 per night
includes taxes & fees
Image gallery for Cayman Reef Resort, Seven Mile Beach. 3 Bed 2 Bath Condo, with Pool & Tennis
9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Cayman Reef Resort, Seven Mile Beach. 3 Bed 2 Bath Condo, with Pool & Tennis
George Town
5% off
Price is S$6,803
S$6,803
for 7 nights, 1 apartment
S$972 per night
includes taxes & fees
Image gallery for 7 Mile Luxury Beach Club. Ocean views from Roof Terrace and Pool Pavilion.
1010 out of 10, Exceptional, (67 reviews)
Exceptional
(67 reviews)
7 Mile Luxury Beach Club. Ocean views from Roof Terrace and Pool Pavilion.
West Bay
5% off
Price is S$13,412
S$13,412
for 7 nights, 1 apartment
S$1,916 per night
includes taxes & fees
Image gallery for Bahama Beach Club in Paradise, Treasure Cay Beachfront, ground floor condo
9.69.6 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Bahama Beach Club in Paradise, Treasure Cay Beachfront, ground floor condo
Treasure Cay
7% off
Price is S$5,386
S$5,386
for 7 nights, 1 apartment
S$769 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$11,447
S$11,447
for 7 nights, 1 villa
S$1,635 per night
includes taxes & fees
Image gallery for East End Dream, RESORT LIVING WITHOUT ANY EXTRA FEES!
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
East End Dream, RESORT LIVING WITHOUT ANY EXTRA FEES!
Grand Cayman
8% off
Price is S$2,961
S$2,961
for 7 nights, 1 apartment
S$423 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Caribbean
Magen's Bay Luxury Beachfront Villa // 10% off September 2026 Weeks
Sleeps 24 · 8 bedrooms · 9+ bathrooms
1010 out of 10
Exceptionalexceptional
110 reviews(110 reviews)
Villas Agua Dulce
Sleeps 12 · 5 bedrooms
9.89.8 out of 10
Exceptionalexceptional
18 reviews(18 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
140 reviews(140 reviews)
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)
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)