Caribbean holiday rentals
We found 63,910 holiday rentals — enter your dates for availability
Popular Caribbean destinations on Stayz
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:12 Sept - 19 Sept
Image gallery for 6 bedroom Villa and Pool side Villa with Private Pool, Sleeps 12
9.69.6 out of 10 rating
Exceptional
(71 reviews)
6 bedroom Villa and Pool side Villa with Private Pool, Sleeps 12
St. Thomas, St Thomas
7% off
Price is AU$7,368
AU$7,368
AU$1,053 per night
includes taxes & fees
Image gallery for The View has amazing vistas and an infinity pool
1010 out of 10 rating
Exceptional
(16 reviews)
The View has amazing vistas and an infinity pool
Gros Islet
8% off
Price is AU$7,725
AU$7,725
AU$1,104 per night
includes taxes & fees
Image gallery for At The Center of it All, Casa Terra Porto #2
1010 out of 10 rating
Exceptional
(9 reviews)
At The Center of it All, Casa Terra Porto #2
San Juan
8% off
Price is AU$1,978
AU$1,978
AU$283 per night
includes taxes & fees
Image gallery for Best Panoramic Ocean View !!! You need to be here to believe it !!!
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Best Panoramic Ocean View !!! You need to be here to believe it !!!
Fajardo
8% off
Price is AU$5,640
AU$5,640
AU$806 per night
includes taxes & fees
Image gallery for Spectacular Villa at Wyndham Rio Mar - Villa Carpe Diem
9.89.8 out of 10 rating
Exceptional
(87 reviews)
Spectacular Villa at Wyndham Rio Mar - Villa Carpe Diem
Río Grande, PR
8% off
Price is AU$4,489
AU$4,489
AU$641 per night
includes taxes & fees
Image gallery for Best Spot in Puerto Rico at Rio Mar Beach & Golf Resort 20 min. to San Juan
9.89.8 out of 10 rating
Exceptional
(83 reviews)
Best Spot in Puerto Rico at Rio Mar Beach & Golf Resort 20 min. to San Juan
Río Grande
8% off
Price is AU$4,565
AU$4,565
AU$652 per night
includes taxes & fees
Image gallery for 15% weekly discounts. 180° Ocean View hacienda - ideal for families & kids.
9.89.8 out of 10 rating
Exceptional
(31 reviews)
15% weekly discounts. 180° Ocean View hacienda - ideal for families & kids.
Camuy
13% off
Price is AU$7,479
AU$7,479
AU$1,068 per night
includes taxes & fees
Image gallery for Luxury Sunshine Villa -outdoor movie screen & pool heated(50x17ft), CHEF & staff
1010 out of 10 rating
Exceptional
(90 reviews)
Luxury Sunshine Villa -outdoor movie screen & pool heated(50x17ft), CHEF & staff
Punta Cana, La Altagracia
5% off
Price is AU$11,044
AU$11,044
AU$1,578 per night
includes taxes & fees
Image gallery for Beautiful Oceanfront Condo
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Beautiful Oceanfront Condo
Red Hook, St Thomas
8% off
Price is AU$2,912
AU$2,912
AU$416 per night
includes taxes & fees
Image gallery for On the beach Villa; free parking, walk to restaurants, minutes from the airport
9.89.8 out of 10 rating
Exceptional
(16 reviews)
On the beach Villa; free parking, walk to restaurants, minutes from the airport
San Juan
8% off
Price is AU$4,356
AU$4,356
AU$622 per night
includes taxes & fees
Image gallery for Discount June 14-28, Luxury Waterfront 6BR home, infinity pool, boat dock, kayak
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Discount June 14-28, Luxury Waterfront 6BR home, infinity pool, boat dock, kayak
Great Guana Cay, Hope Town
9% off
Price is AU$23,391
AU$23,391
AU$3,342 per night
includes taxes & fees
Image gallery for Luxury Villa - 4 Bedroom Waterfront Property
1010 out of 10 rating
Exceptional
(11 reviews)
Luxury Villa - 4 Bedroom Waterfront Property
Providenciales
8% off
Price is AU$12,878
AU$12,878
AU$1,840 per night
includes taxes & fees
Image gallery for SUMMER SPECIAL! Beach front residence with Breathtaking Heated infinity pool
9.49.4 out of 10 rating
Exceptional
(80 reviews)
SUMMER SPECIAL! Beach front residence with Breathtaking Heated infinity pool
Nassau, New Providence
9% off
Price is AU$14,627
AU$14,627
AU$2,090 per night
includes taxes & fees
Image gallery for The Stone House, Marigot Bay- Character, Comfort, Private Pool, Wonderful View
1010 out of 10 rating
Exceptional
(84 reviews)
The Stone House, Marigot Bay- Character, Comfort, Private Pool, Wonderful View
Marigot Bay
9% off
Price is AU$4,713
AU$4,713
AU$673 per night
includes taxes & fees
Image gallery for Beautifully newly renovated 3 BR/4 BA condo footsteps from the beach.
1010 out of 10 rating
Exceptional
(30 reviews)
Beautifully newly renovated 3 BR/4 BA condo footsteps from the beach.
St. Thomas, USVI
11% off
Price is AU$7,120
AU$7,120
AU$1,017 per night
includes taxes & fees
Image gallery for Featured on HGTV! Sea Cliff Villa at Bolongo Bay
1010 out of 10 rating
Exceptional
(70 reviews)
Featured on HGTV! Sea Cliff Villa at Bolongo Bay
St. Thomas
8% off
Price is AU$3,770
AU$3,770
AU$539 per night
includes taxes & fees
Image gallery for Rosalie Apartment Ocean Front Villa Accommodation
9.69.6 out of 10 rating
Exceptional
(58 reviews)
Rosalie Apartment Ocean Front Villa Accommodation
Oistins, Christ Church
9% off
Price is AU$1,788
AU$1,788
AU$255 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 AU$19,736
AU$19,736
AU$2,819 per night
includes taxes & fees
Image gallery for Modern Open Air 2 Bedroom Villa - Private Pool & Spectacular Sea & Piton View
9.69.6 out of 10 rating
Exceptional
(167 reviews)
Modern Open Air 2 Bedroom Villa - Private Pool & Spectacular Sea & Piton View
Soufrière, Malgretoute
8% off
Price is AU$4,663
AU$4,663
AU$666 per night
includes taxes & fees
Image gallery for This is a beach front Condo located in Isla Verde Puerto Rico
9.89.8 out of 10 rating
Exceptional
(59 reviews)
This is a beach front Condo located in Isla Verde Puerto Rico
Carolina
9% off
Price is AU$3,030
AU$3,030
AU$433 per night
includes taxes & fees
Image gallery for "Seaside Serenity: Experience Spectacular Ocean Views!"
1010 out of 10 rating
Exceptional
(76 reviews)
"Seaside Serenity: Experience Spectacular Ocean Views!"
St. Thomas
8% off
Price is AU$6,588
AU$6,588
AU$941 per night
includes taxes & fees
Image gallery for Caribbean Oasis - Spacious Beach Front Villa
9.89.8 out of 10 rating
Exceptional
(163 reviews)
Caribbean Oasis - Spacious Beach Front Villa
Humacao, Punta Santiago
8% off
Price is AU$6,596
AU$6,596
AU$942 per night
includes taxes & fees
Image gallery for Modern Beachfront 2brdm-2bath with glass pool & incredible view !
9.89.8 out of 10 rating
Exceptional
(74 reviews)
Modern Beachfront 2brdm-2bath with glass pool & incredible view !
Providenciales, Caicos Islands
8% off
Price is AU$9,958
AU$9,958
AU$1,423 per night
includes taxes & fees
Image gallery for M/H(#2⭐️)AC the whole house near the airport
9.09.0 out of 10 rating
Wonderful
(42 reviews)
M/H(#2⭐️)AC the whole house near the airport
Carolina
12% off
Price is AU$1,821
AU$1,821
AU$260 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
SPECTACULAR VILLA with Electronic Gates, Private Pool and Tropical Gardens
Sleeps 6 · 3 bedrooms · 2+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
45 reviews(45 reviews)
Bay View vacation Rentals Villa # 1
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
14 reviews(14 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
32 reviews(32 reviews)
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)
The Rising Sun! - Private Island Getaway
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Secluded Waterfront Villa with Private Pool – 3,000 Sq. Ft. of Luxury
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
185 reviews(185 reviews)