Island holiday rentals in Caribbean
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Top-rated island rentals in Caribbean
Guests agree: these island rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for island rentals in Caribbean
Family-friendly island rentals
Villa in Samana, Dominican Republic
4.8 out of 5 average rating, 46 reviewsVilla Oceanfront beach access and swim pool Samana
8–15 Dec
Home in Current, Bahamas
4.75 out of 5 average rating, 175 reviewsThe Tree House, Eleuthera, Bahamas
23 Feb – 2 Mar
Villa in Soufriere, St. Lucia
5.0 out of 5 average rating, 92 reviewsLa Batterie Villa • Boutique Villa • Amazing Views
21–28 Apr
Villa in Duncans bay, Jamaica
4.89 out of 5 average rating, 75 reviewsSharkfin Villa, family beach house
3–10 Apr
Villa in Salybia, Dominica
4.95 out of 5 average rating, 86 reviewsVilla Ayahora and Aywasi
26 Sep – 3 Oct
Home in La Trinité, Martinique
5.0 out of 5 average rating, 93 reviews4-star Vert Azur villa
3–10 Nov
Villa in Saint-Barthélemy, St. Barthélemy
4.94 out of 5 average rating, 70 reviewsVilla TIWA
8–15 Oct
Home in Grand Cayman, Cayman Islands
4.96 out of 5 average rating, 47 reviewsSnorkelers Beachfront Paradise - Beach Plum Villa
6–13 Sep
Island rentals with a patio
Villa in Wesley Will, British Virgin Islands
5.0 out of 5 average rating, 27 reviewsVilla Naku, escape and relax.
3–10 Oct
Villa in Providenciales, Turks & Caicos Islands
4.93 out of 5 average rating, 42 reviews‘My Little Hideaway’ at Lucayan Cays
27 Jan – 3 Feb
Villa in Nail Bay, British Virgin Islands
5.0 out of 5 average rating, 7 reviewsBoulder Crest, Pool, March 20th to 26th $700pn
1–8 May
Flat in Venice, Florida, US
4.92 out of 5 average rating, 25 reviewsVenice Island Tropical Oasis w Spa/Outdoor Kitchen
14–21 Aug
Cottage in Gregory Town, Bahamas
4.96 out of 5 average rating, 51 reviewsSwell - Cozy Oceanfront Eco-Cottage
11–18 Sep
Villa in Treasure Beach, Jamaica
5.0 out of 5 average rating, 3 reviewsDestiny Private 2-Bedroom Beachfront w/ 2 Pools
30 Nov – 7 Dec
Villa in Flamenco, Puerto Rico
4.9 out of 5 average rating, 86 reviewsCulebra Beach Villa #2 on Exclusive Flamenco Beach
7–14 Jul
Home in Micoud, St. Lucia
4.81 out of 5 average rating, 21 reviewsChateau Joyeux
2–9 Sep
Home in Captiva, Florida, US
4.86 out of 5 average rating, 7 reviewsOcean views, sleeps 10, heated pool, 2 golf carts
15–22 Oct
Villa in Micoud, St. Lucia
4.85 out of 5 average rating, 97 reviewsSequoia Villa - Luxury Villa in St Lucia, Perfect!
7–14 Sep
Flat in Kralendijk, Bonaire, Sint Eustatius and Saba
4.77 out of 5 average rating, 22 reviewsOceanfront 2 bedroom Lodge Sunset Beach Salt
13–20 Feb
Apartment in George Town, Bahamas
4.91 out of 5 average rating, 87 reviewsBeautiful Beachside Luxury Apartment, Mainfloor ✨
20–27 Oct
Home in Cul-de-Sac, St. Martin
4.93 out of 5 average rating, 27 reviewsVilla Zen : confort et luxe vue mer St Martin
21–28 Oct
Home in Isla Baru, Colombia
4.83 out of 5 average rating, 75 reviewsCasa de Sirenas Beach House, Isle of Baru
15–22 Dec
Apartment in FreeTown, Antigua & Barbuda
4.92 out of 5 average rating, 50 reviewsNonsuch Bay Private Apt by Pool-full A/C all rooms
19–26 Jul
Home in Woodlands, Montserrat
4.83 out of 5 average rating, 6 reviewsFamily Beachside Living with Oceanviews & Pool
25 Aug – 1 Sep
Destinations to explore
- Rentals with breakfast Caribbean
- Apartment rentals Caribbean
- Rentals with a firepit Caribbean
- Smoking-friendly rentals Caribbean
- Rentals with an EV charger Caribbean
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- Rentals with a washing machine and dryer Caribbean
- Chalet rentals Caribbean
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- Cabin rentals Caribbean
- Nature eco lodge rentals Caribbean
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- Rentals with an accessible-height toilet Caribbean
- Monthly Rentals Caribbean
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