Caribbean holiday rentals
We found 65,110 holiday rentals — enter your dates for availability
Popular cities in Caribbean
St. Thomas
St. Thomas
St. John
St. John
San Juan (and vicinity)
San Juan (and vicinity)
Providenciales
Providenciales
Nassau
Nassau
George Town
George Town
Holiday rentals with weekly discounts - Caribbean
Showing deals for:17 Oct - 24 Oct
Image gallery for Luxury Oceanview Glamping @ Punta Flamenco, Culebra, Puerto Rico
1010 out of 10 rating
Exceptional
(7 reviews)
Luxury Oceanview Glamping @ Punta Flamenco, Culebra, Puerto Rico
Culebra
8% off
Price is S$6,133
S$6,133
S$876 per night
includes taxes & fees
Image gallery for breathtaking sea view Beach FRONT very PRIVATE and quiet SOLAR POWERED
8.28.2 out of 10 rating
Very good
(12 reviews)
breathtaking sea view Beach FRONT very PRIVATE and quiet SOLAR POWERED
Arecibo
20% off
Price is S$2,816
S$2,816
S$402 per night
includes taxes & fees
Image gallery for House with amazing architecture with private pool and full A/C.
9.29.2 out of 10 rating
Wonderful
(38 reviews)
House with amazing architecture with private pool and full A/C.
Cabo Rojo
8% off
Price is S$3,125
S$3,125
S$446 per night
includes taxes & fees
Image gallery for Luxury villa with sky pool and scenic ocean views, 10 mins from airport
1010 out of 10 rating
Exceptional
(43 reviews)
Luxury villa with sky pool and scenic ocean views, 10 mins from airport
Laborie
5% off
Price is S$2,352
S$2,352
S$336 per night
includes taxes & fees
Image gallery for Anchor's Away, Russell Island
1010 out of 10 rating
Exceptional
(33 reviews)
Anchor's Away, Russell Island
Russell Island, BS
8% off
Price is S$2,189
S$2,189
S$313 per night
includes taxes & fees
Image gallery for Paradise Found! Cozy 2-bedroom condo with AC and WiFi in fabulous Bimini Bay
1010 out of 10 rating
Exceptional
(15 reviews)
Paradise Found! Cozy 2-bedroom condo with AC and WiFi in fabulous Bimini Bay
Alice Town, Biminy
8% off
Price is S$2,750
S$2,750
S$393 per night
includes taxes & fees
Image gallery for Luxury Villa with Pool, Heated Jacuzzi, & Terrace in El Yunque Rainforest
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Luxury Villa with Pool, Heated Jacuzzi, & Terrace in El Yunque Rainforest
Río Grande
8% off
Price is S$5,388
S$5,388
S$770 per night
includes taxes & fees
Image gallery for Bimini Home at the Beach
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Bimini Home at the Beach
Alice Town
9% off
Price is S$2,828
S$2,828
S$404 per night
includes taxes & fees
Image gallery for $1MIL PITON VILLA VIEW - COLOMBETTE
8.88.8 out of 10 rating
Excellent
(8 reviews)
$1MIL PITON VILLA VIEW - COLOMBETTE
Soufrière, Soufriere
8% off
Price is S$3,580
S$3,580
S$511 per night
includes taxes & fees
Image gallery for Bliss at Cap-- fabulous views!
9.89.8 out of 10 rating
Exceptional
(76 reviews)
Bliss at Cap-- fabulous views!
Gros Islet
9% off
Price is S$4,243
S$4,243
S$606 per night
includes taxes & fees
Image gallery for 4 bdrm, 3 bath Beachfront Villa w/ 48 ft pool & Best Sunsets on the Island!
1010 out of 10 rating
Exceptional
(116 reviews)
4 bdrm, 3 bath Beachfront Villa w/ 48 ft pool & Best Sunsets on the Island!
Providenciales, Caicos Islands
8% off
Price is S$14,478
S$14,478
S$2,068 per night
includes taxes & fees
Image gallery for 2 acre Waterfront Estate (unbelievable views, 2 Pools, Kayaks,)
9.09.0 out of 10 rating
Wonderful
(26 reviews)
2 acre Waterfront Estate (unbelievable views, 2 Pools, Kayaks,)
Providenciales, Caicos Islands
8% off
Price is S$17,864
S$17,864
S$2,552 per night
includes taxes & fees
Image gallery for Sunset Villa in Exclusive Palm Cay Beachfront Resort- A Retreat w/Pool Access
1010 out of 10 rating
Exceptional
(150 reviews)
Sunset Villa in Exclusive Palm Cay Beachfront Resort- A Retreat w/Pool Access
Nassau, New Providence
12% off
Price is S$3,349
S$3,349
S$478 per night
includes taxes & fees
Image gallery for 5 minute walk to the beach m 2 BR cottage with old school island pool.
9.09.0 out of 10 rating
Wonderful
(6 reviews)
5 minute walk to the beach m 2 BR cottage with old school island pool.
St. Thomas, St Thomas
8% off
Price is S$2,157
S$2,157
S$308 per night
includes taxes & fees
Image gallery for Enjoy a magnificent experience in Vieques Bioluminescent Bay!
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Enjoy a magnificent experience in Vieques Bioluminescent Bay!
Vieques
8% off
Price is S$2,547
S$2,547
S$364 per night
includes taxes & fees
Image gallery for Private 4 -bed home w/ dock facing the Hilton Hotel.
1010 out of 10 rating
Exceptional
(7 reviews)
Private 4 -bed home w/ dock facing the Hilton Hotel.
Alice Town, Bimini
8% off
Price is S$14,085
S$14,085
S$2,012 per night
includes taxes & fees
Image gallery for Oceanfront! Saltwater Pool. Walk to Beach & Restaurants. Northshore, St. Croix
1010 out of 10 rating
Exceptional
(50 reviews)
Oceanfront! Saltwater Pool. Walk to Beach & Restaurants. Northshore, St. Croix
Kingshill, St Croix
7% off
Price is S$2,672
S$2,672
S$382 per night
includes taxes & fees
Image gallery for Cozy stone studio cottage on private pink sand beach
9.89.8 out of 10 rating
Exceptional
(92 reviews)
Cozy stone studio cottage on private pink sand beach
Double Bay, Central Eleuthera
9% off
Price is S$2,324
S$2,324
S$332 per night
includes taxes & fees
Image gallery for Fort Recovery Beachfront Villa and Suites Hotel 1BR
1010 out of 10 rating
Exceptional
(17 reviews)
Fort Recovery Beachfront Villa and Suites Hotel 1BR
West End, Tortola
8% off
Price is S$2,343
S$2,343
S$335 per night
includes taxes & fees
Image gallery for Whistling Duck: Private Oceanfront Cottage
1010 out of 10 rating
Exceptional
(29 reviews)
Whistling Duck: Private Oceanfront Cottage
Clarence Town, Long Island
5% off
Price is S$1,993
S$1,993
S$285 per night
includes taxes & fees
Image gallery for The Villa Michelle • Luxury • Heated Pool • Generator
1010 out of 10 rating
Exceptional
(6 reviews)
The Villa Michelle • Luxury • Heated Pool • Generator
St. Thomas, St Thomas
8% off
Price is S$7,563
S$7,563
S$1,080 per night
includes taxes & fees
Image gallery for Ranked by VRBO/HomeAway Top 10 Most Unique Rentals Worldwide, Walk to Town.
9.89.8 out of 10 rating
Exceptional
(138 reviews)
Ranked by VRBO/HomeAway Top 10 Most Unique Rentals Worldwide, Walk to Town.
Alice Town, Central Eleuthera
9% off
Price is S$2,133
S$2,133
S$305 per night
includes taxes & fees
Image gallery for Beautiful Ocean View 3 Bedroom Condo on the Beach
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Beautiful Ocean View 3 Bedroom Condo on the Beach
Providenciales, Caicos Islands
8% off
Price is S$4,225
S$4,225
S$604 per night
includes taxes & fees
Image gallery for Old Bahama Bay, Private newer home, deep water dock, pool, West End, Bahamas
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Old Bahama Bay, Private newer home, deep water dock, pool, West End, Bahamas
West End, Grand Bahama Island
9% off
Price is S$15,225
S$15,225
S$2,175 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Caribbean
5 bedroom relaxation Oceanfront w/ Stunning natural views. 5 bdrms, sleeps 12
Sleeps 12 · 5 bedrooms · 3 bathrooms
9.49.4 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Spectacular BEACHFRONT luxury Villa with private pool, Jacuzzi chef, full staff
Sleeps 24 · 11 bedrooms · 12+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Bay View vacation Rentals Villa # 1
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
Secluded Waterfront Single Family Villa with Private Pool – 3,000 Sq of Luxury
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
186 reviews(186 reviews)
Casa Del Mar - Beach Front with Endless Views
Sleeps 18 · 7 bedrooms · 6 bathrooms
9.09.0 out of 10
Wonderfulwonderful
20 reviews(20 reviews)
Great House Villa
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
72 reviews(72 reviews)