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
Home in Sugarloaf Key, Florida, US
4.75 out of 5 average rating, 112 reviewsBungalows at Sugarloaf Beach - Mi Azucar
2–9 Apr
Villa in Samana, Dominican Republic
4.8 out of 5 average rating, 46 reviewsVilla Oceanfront beach access and swim pool Samana
7–14 Nov
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, 93 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
15–22 Oct
Villa in Salybia, Dominica
4.95 out of 5 average rating, 86 reviewsVilla Ayahora and Aywasi
26 Sept – 3 Oct
Home in La Trinité, Martinique
5.0 out of 5 average rating, 93 reviews4-star Vert Azur villa
23–30 Aug
Home in Tola, Nicaragua
4.62 out of 5 average rating, 78 reviewsCasa Guacalito - Ocean View Villa, Sleeps 8
28 May – 4 Jun
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
11–18 Feb
Flat in Venice, Florida, US
4.92 out of 5 average rating, 25 reviewsVenice Island Tropical Oasis w Spa/Outdoor Kitchen
2–9 Oct
Cottage in Gregory Town, Bahamas
4.96 out of 5 average rating, 51 reviewsSwell - Cozy Oceanfront Eco-Cottage
11–18 Sept
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
24 Apr – 1 May
Home in Governor's Harbour, Bahamas
5.0 out of 5 average rating, 18 reviewsOcean Front Home, Banks Road, Governor’s Harbour
16–23 Aug
Villa in Mount Irvine Bay, Trinidad & Tobago
4.87 out of 5 average rating, 15 reviewsHeated Saltwater Pool, Lush Garden, Beach
21–28 Jun
Home in Captiva, Florida, US
4.86 out of 5 average rating, 7 reviewsOcean views, sleeps 10, heated pool, 2 golf carts
17–24 Oct
Villa in Micoud, St. Lucia
4.85 out of 5 average rating, 98 reviewsSequoia Villa - Luxury Villa in St Lucia, Perfect!
20–27 Feb
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, 88 reviewsBeautiful Beachside Luxury Apartment, Mainfloor ✨
6–13 Feb
Home in Cul-de-Sac, St. Martin
4.93 out of 5 average rating, 27 reviewsVilla Zen : confort et luxe vue mer St Martin
24–31 Mar
Cottage in St. James Parish W.I, Jamaica
4.94 out of 5 average rating, 85 reviewsHorizon Cottage - Sea Ranch, Belmont Jamaica
28 Nov – 5 Dec
Home in Isla Baru, Colombia
4.83 out of 5 average rating, 75 reviewsCasa de Sirenas Beach House, Isle of Baru
2–9 Aug
Apartment in FreeTown, Antigua & Barbuda
4.92 out of 5 average rating, 50 reviewsNonsuch Bay Private Apt by Pool-full A/C all rooms
4–11 Jul
Destinations to explore
- Family-friendly rentals Caribbean
- Tiny house rentals Caribbean
- Guest house rentals Caribbean
- Ski-in/ski-out rentals Caribbean
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