Resort holiday rentals in Caribbean
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Top-rated resort rentals in Caribbean
Guests agree: these resort rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for resort rentals in Caribbean
Family-friendly resort rentals
Resort in Puerto Plata, Dominican Republic
4.85 out of 5 average rating, 13 reviewsLifestyle Suite Vip Gold All Inclusive Included
9–16 Mar
Resort in Philipsburg, Sint Maarten
5.0 out of 5 average rating, 3 reviewsSimpson Bay Resort and Marina
16–23 Aug
Resort in La Cruz, Costa Rica
4.66 out of 5 average rating, 70 reviewsBlue Dream, Nature by the Bahia Salinas Sea
16–23 Sep
Resort in Grace Bay, Turks & Caicos Islands
5.0 out of 5 average rating, 32 reviewsVilla Renaissance Poolside 1BR - Peloton Bike
29 Jul – 5 Aug
Resort in Río Grande, Puerto Rico
4.84 out of 5 average rating, 61 reviewsWyndham Riomar Villa with 2 Golf Carts
7–14 Aug
Hotel room in Nosara, Costa Rica
4.7 out of 5 average rating, 50 reviewsK-Rae's Irish Pub and Inn - Ocean Blue
8–15 Apr
Resort in Road Town, British Virgin Islands
5.0 out of 5 average rating, 5 reviewsFort Recovery Villa and Suites hotel 1BR deluxe
11–18 Mar
Hotel room in Fort Lauderdale, Florida, US
5.0 out of 5 average rating, 5 reviewsFt Lauderdale's Marriott's BeachPlace Towers 2bdr
13–20 Jan
Resort rentals with a pool
Resort in Puerto Plata, Dominican Republic
5.0 out of 5 average rating, 4 reviewsThe Tropical Hotel: Sleeps 2-4, All-Inclusive
26 Aug – 2 Sep
Resort in Anna Maria, Florida, US
4.98 out of 5 average rating, 62 reviewsBlue Dolphin AMI Jacaranda Lower 2b/1b
12–19 Oct
Resort in Sunny Isles Beach, Florida, US
4.88 out of 5 average rating, 24 reviewsLuxury Beach Resort - Studio w/ Ocean View
28 Sep – 5 Oct
Resort in Bonita Springs, Florida, US
5.0 out of 5 average rating, 8 reviewsWaterfront Gulf Access - 4 Bedroom W Heated Pool
6–13 Jan
Resort in Holmes Beach, Florida, US
4.88 out of 5 average rating, 16 reviewsThe Royal Villa Two bedroom, Two bath, Pool ,Beach
13–20 Dec
Resort in Siesta Key, Florida, US
5.0 out of 5 average rating, 32 reviews1936 Beach house across street from beach
13–20 Dec
Resort in East End, U.S. Virgin Islands
5.0 out of 5 average rating, 11 reviewsMargaritaville St. Thomas-Luxury Beach Vacation
29 Jun – 6 Jul
Resort in Nassau, Bahamas
5.0 out of 5 average rating, 3 reviewsLuxury Beach Resort - VIP JR Suite in Bahamas
15–22 Oct
Resort rentals with a gym
Resort in Hollywood, Florida, US
4.83 out of 5 average rating, 47 reviewsHydeHotel/Residences 2bdr/2bth Beach/ocean view
10–17 Jul
Resort in Sunny Isles Beach, Florida, US
4.82 out of 5 average rating, 11 reviewsAmazing Beachside Studio/ Condo
5–12 Jun
Resort in Sunny Isles Beach, Florida, US
4.68 out of 5 average rating, 56 reviewsOcean view 2 Bed/3 Bath
27 Sep – 4 Oct
Resort in Sunny Isles Beach, Florida, US
4.8 out of 5 average rating, 131 reviewsBeach Resort Suite with Direct Ocean view!
8–15 Dec
Resort in Cabarete, Dominican Republic
4.56 out of 5 average rating, 9 reviewsLuxury Cabarete 3BR Suite w/ Balcony & Pool
31 Mar – 7 Apr
Resort in East End, U.S. Virgin Islands
4.73 out of 5 average rating, 11 reviewsMargaritaville Vacation Club St. Thomas Studio
20–27 Mar
Resort in Key Largo, Florida, US
4.87 out of 5 average rating, 85 reviewsUltimate Getaway! Private Beach Access, Pools
7–14 Sep
Resort in Miami, Florida, US
4.59 out of 5 average rating, 76 reviewsMiami Suites w/ Bay Views & Hotel Amenities ! ! !
1–8 Feb
Destinations to explore
- Family-friendly rentals Caribbean
- Tiny house rentals Caribbean
- Guest house rentals Caribbean
- Ski-in/ski-out rentals Caribbean
- Cabin rentals Caribbean
- Rentals with a cinema Caribbean
- Bed and breakfasts Caribbean
- Campsite rentals Caribbean
- Beach house rentals Caribbean
- Earth house rentals Caribbean
- Villa rentals Caribbean
- Pet-friendly rentals Caribbean
- Houseboat rentals Caribbean
- Rentals with an accessible-height bed Caribbean
- Rentals with a fireplace Caribbean
- Cottage rentals Caribbean
- Holiday home rentals Caribbean
- Treehouse rentals Caribbean
- Boutique hotel rentals Caribbean
- Rentals with a hot tub Caribbean
- Rentals with a kayak Caribbean
- Rentals with a washing machine and dryer Caribbean
- House rentals Caribbean
- Bungalow rentals Caribbean
- Townhouse rentals Caribbean
- Apartment rentals Caribbean
- Serviced apartment rentals Caribbean
- Rentals with breakfast Caribbean
- Chalet rentals Caribbean
- Tent rentals Caribbean
- Waterfront rentals Caribbean
- Monthly Rentals Caribbean
- Rentals with beach access Caribbean
- Loft rentals Caribbean
- Motorhome rentals Caribbean
- Rentals with pools Caribbean
- Family-friendly rentals Caribbean
- Wheelchair-accessible rentals Caribbean
- Luxury rentals Caribbean
- Rentals with a sauna Caribbean
- Nature eco lodge rentals Caribbean
- Rentals with an accessible-height toilet Caribbean
- Fitness-friendly rentals Caribbean
- Container rentals Caribbean
- Island rentals Caribbean
- Aparthotel rentals Caribbean
- Beachfront rentals Caribbean
- Rentals with a patio Caribbean
- Private suite rentals Caribbean
- Farm stay rentals Caribbean
- Rentals with outdoor seating Caribbean
- Hostel rentals Caribbean
- Rentals with lake access Caribbean
- Boat rentals Caribbean
- Hotel rentals Caribbean
- Flat rentals Caribbean
- Rentals with a balcony Caribbean
- Rentals with a firepit Caribbean
- Smoking-friendly rentals Caribbean
- Rentals with an EV charger Caribbean
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom