Chalet holiday rentals in Caribbean
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Top-rated chalet rentals in Caribbean
Guests agree: these chalets are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for chalet rentals in Caribbean
Family-friendly chalet rentals
Chalet in Osbourn, Antigua & Barbuda
4.91 out of 5 average rating, 116 reviewsGrace Inn 2 bedrooms - Certified
30 Oct – 6 Nov
Chalet in Rio Grande, Puerto Rico
4.79 out of 5 average rating, 262 reviewsEl Yunque Chalet, PRIVATE POOL, NEWLY RENOVATED!
15–22 Sep
Chalet in Provincia de Guanacaste, Costa Rica
4.86 out of 5 average rating, 65 reviewsMarbella Beach (10min. walk) Nature Lovers & Surf
6–13 Apr
Chalet in Río Grande, Puerto Rico
4.9 out of 5 average rating, 68 reviewsChalet del Yunque, Puerto Rico
12–19 Dec
Chalet in Vieques, Puerto Rico
4.74 out of 5 average rating, 142 reviewsOcean View Chalet Sunny Dream
4–9 Jul
Chalet in Turbaco, Colombia
4.78 out of 5 average rating, 27 reviewsIDEAL PLACE TO ENJOY NATURE
5–12 Aug
Chalet in Naranjo, Costa Rica
4.87 out of 5 average rating, 47 reviewsFinca La Petisa Coffee Plantation Chalet
2–9 Nov
Chalet in Basse-Terre, Guadeloupe
4.94 out of 5 average rating, 50 reviewsLe Val de lys
14–21 Jan
Luxury chalet rentals
Chalet in Lake Placid, Florida, US
4.93 out of 5 average rating, 30 reviewsLakefront Home, 2 King Beds, Kayak, Large Kitchen
22–29 Jul
Chalet in Bonita Springs, Florida, US
5.0 out of 5 average rating, 31 reviewsMARBEYA
29 Sep – 6 Oct
Chalet in Rincon, Puerto Rico
4.77 out of 5 average rating, 92 reviewsWelcome to the jungle Beach-house & private pool!
24–31 Mar
Chalet in Siesta Key, Florida, US
New place to stayBeach Chalet Condo - Ocean View - Walkability!
24 Nov – 1 Dec
Chalet in Cartagena , Colombia
5.0 out of 5 average rating, 8 reviewsAmazing Beach House in Bocachica
23–30 Nov
Chalet in Central Eleuthera, Bahamas
5.0 out of 5 average rating, 6 reviewsUnicorn Cay Beachfront Estate Governor's Harbour
27 Feb – 6 Mar
Chalet in Jarabacoa, Dominican Republic
4.43 out of 5 average rating, 7 reviewsFantastic Harmony Chalet in Pinar del Sol
3–10 Jul
Chalet in Santo Domingo Norte, Dominican Republic
Rancho verde
12–19 Dec
Lakefront chalet rentals
Chalet in Utuado, Puerto Rico
4.92 out of 5 average rating, 202 reviewsCASA LAGO- lake house retreat, kayaks, hot tub
16–23 Aug
Chalet in Pointe Noire, Guadeloupe
4.71 out of 5 average rating, 7 reviewsChalet "La Danse du Tambour"
14–21 Nov
Chalet in Caguana, Puerto Rico
4.96 out of 5 average rating, 26 reviewsMountain chalet with hiking trails and river pool
14–21 Apr
Chalet in Chichiriviche, Venezuela
4.8 out of 5 average rating, 5 reviewsVacation Home Plaza Mayor.
16–23 Jul
Chalet in Santa Marta, Colombia
4.8 out of 5 average rating, 5 reviewsSanta Marta/CaboTortuga Beach •Casa Alquimia
5–12 Jun
Chalet in Freeport, Bahamas
4.47 out of 5 average rating, 15 reviewsSafe Romantic Getaway, Water Views - Private Dock
28 Mar – 4 Apr
Chalet in Le Vauclin, Martinique
Eco-lodge /Relay point on the Caps Trace
27 Mar – 3 Apr
Place to stay in Playa Larga, Cuba
4.43 out of 5 average rating, 42 reviewsPlaya Larga Holiday Home
12–19 Oct
Destinations to explore
- Nature eco lodge rentals Caribbean
- Ski-in/ski-out rentals Caribbean
- Rentals with outdoor seating Caribbean
- House rentals Caribbean
- Beach house rentals Caribbean
- Earth house rentals Caribbean
- Holiday home rentals Caribbean
- Motorhome rentals Caribbean
- Rentals with a firepit Caribbean
- Smoking-friendly rentals Caribbean
- Rentals with a washing machine and dryer Caribbean
- Beachfront rentals Caribbean
- Bungalow rentals Caribbean
- Townhouse rentals Caribbean
- Container rentals Caribbean
- Farm stay rentals Caribbean
- Boutique hotel rentals Caribbean
- Rentals with lake access Caribbean
- Rentals with breakfast Caribbean
- Rentals with beach access Caribbean
- Loft rentals Caribbean
- Family-friendly rentals Caribbean
- Wheelchair-accessible rentals Caribbean
- Cabin rentals Caribbean
- Cottage rentals Caribbean
- Bed and breakfasts Caribbean
- Rentals with pools Caribbean
- Rentals with an EV charger Caribbean
- Island rentals Caribbean
- Boat rentals Caribbean
- Hostel rentals Caribbean
- Luxury rentals Caribbean
- Serviced apartment rentals Caribbean
- Rentals with an accessible-height bed Caribbean
- Rentals with a balcony Caribbean
- Rentals with a patio Caribbean
- Houseboat rentals Caribbean
- Rentals with a hot tub Caribbean
- Rentals with a kayak Caribbean
- Villa rentals Caribbean
- Pet-friendly rentals Caribbean
- Apartment rentals Caribbean
- Guest house rentals Caribbean
- Hotel rentals Caribbean
- Flat rentals Caribbean
- Rentals with an accessible-height toilet Caribbean
- Rentals with a cinema Caribbean
- Rentals with a sauna Caribbean
- Fitness-friendly rentals Caribbean
- Monthly Rentals Caribbean
- Tent rentals Caribbean
- Waterfront rentals Caribbean
- Treehouse rentals Caribbean
- Rentals with a fireplace Caribbean
- Aparthotel rentals Caribbean
- Private suite rentals Caribbean
- Resort rentals Caribbean
- Campsite rentals Caribbean
- Family-friendly rentals Caribbean
- Tiny house rentals Caribbean
- Yurt Rentals United States
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- Houseboats United States
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- Farm Houses United States
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