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
17–24 Jul
Chalet in Rio Grande, Puerto Rico
4.79 out of 5 average rating, 262 reviewsEl Yunque Chalet, PRIVATE POOL, NEWLY RENOVATED!
26 Nov – 3 Dec
Chalet in Provincia de Guanacaste, Costa Rica
4.86 out of 5 average rating, 65 reviewsMarbella Beach (10min. walk) Nature Lovers & Surf
1–8 Sep
Chalet in Río Grande, Puerto Rico
4.9 out of 5 average rating, 68 reviewsChalet del Yunque, Puerto Rico
28 Sep – 5 Oct
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
4–11 Aug
Chalet in Basse-Terre, Guadeloupe
4.94 out of 5 average rating, 50 reviewsLe Val de lys
2–9 Mar
Chalet in Naranjo, Costa Rica
4.87 out of 5 average rating, 47 reviewsFinca La Petisa Coffee Plantation Chalet
2–9 Oct
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
20–27 Nov
Chalet in Bonita Springs, Florida, US
5.0 out of 5 average rating, 30 reviewsMARBEYA
27 Jun – 4 Jul
Chalet in Rincon, Puerto Rico
4.77 out of 5 average rating, 92 reviewsWelcome to the jungle Beach-house & private pool!
28 Mar – 4 Apr
Chalet in Siesta Key, Florida, US
New place to stayBeach Chalet - Deck - Village & Beach Walkable!
23–30 Dec
Chalet in Cartagena , Colombia
5.0 out of 5 average rating, 8 reviewsAmazing Beach House in Bocachica
3–10 Aug
Chalet in Central Eleuthera, Bahamas
5.0 out of 5 average rating, 6 reviewsUnicorn Cay Beachfront Estate Governor's Harbour
1–8 Oct
Chalet in Jarabacoa, Dominican Republic
4.43 out of 5 average rating, 7 reviewsFantastic Harmony Chalet in Pinar del Sol
1–8 Jul
Chalet in Santo Domingo Norte, Dominican Republic
Rancho verde
11–18 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
21–28 Aug
Chalet in Pointe Noire, Guadeloupe
4.71 out of 5 average rating, 7 reviewsChalet "La Danse du Tambour"
12–19 Nov
Chalet in Caguana, Puerto Rico
4.96 out of 5 average rating, 26 reviewsMountain chalet with hiking trails and river pool
5–12 Sep
Chalet in Chichiriviche, Venezuela
4.8 out of 5 average rating, 5 reviewsPlaza Mayor vacation home.
14–21 Jul
Chalet in Santa Marta, Colombia
4.8 out of 5 average rating, 5 reviewsSanta Marta/CaboTortuga Beach •Casa Alquimia
20–27 Nov
Chalet in Freeport, Bahamas
4.47 out of 5 average rating, 15 reviewsSafe Romantic Getaway, Water Views - Private Dock
13–20 Dec
Chalet in Le Vauclin, Martinique
Eco-lodge /Relay point on the Caps Trace
26 Mar – 2 Apr
Place to stay in Playa Larga, Cuba
4.21 out of 5 average rating, 19 reviews**Caleton Playa Larga Hostel**
23–30 Apr
Destinations to explore
- Cottage rentals Caribbean
- Boutique hotel rentals Caribbean
- Resort rentals Caribbean
- Container rentals Caribbean
- Rentals with a balcony Caribbean
- Luxury rentals Caribbean
- Boat rentals Caribbean
- Cabin rentals Caribbean
- Rentals with outdoor seating Caribbean
- Holiday home rentals Caribbean
- Rentals with a hot tub Caribbean
- Rentals with a kayak Caribbean
- Houseboat rentals Caribbean
- Aparthotel rentals Caribbean
- Tent rentals Caribbean
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- House rentals Caribbean
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- Pet-friendly rentals Caribbean
- Serviced apartment rentals Caribbean
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- Bungalow rentals Caribbean
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- Rentals with a washing machine and dryer Caribbean
- Rentals with a cinema Caribbean
- Fitness-friendly rentals Caribbean
- Rentals with breakfast Caribbean
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- Loft rentals Caribbean
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- Guest house rentals Caribbean
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- Private suite rentals Caribbean
- Treehouse rentals Caribbean
- Hostel rentals Caribbean
- Rentals with a sauna Caribbean
- Bed and breakfasts Caribbean
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- Flat rentals Caribbean
- Hotel rentals Caribbean
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- Beach house rentals Caribbean
- Earth house rentals Caribbean
- Rentals with a patio Caribbean
- Monthly Rentals Caribbean
- Family-friendly rentals Caribbean
- Tiny house rentals Caribbean
- Family-friendly rentals Caribbean
- Wheelchair-accessible rentals Caribbean
- Island rentals Caribbean
- Rentals with pools Caribbean
- Nature eco lodge rentals Caribbean
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