Top Chalets in Caribbean in 2026

A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Caribbean chalets

A clear swimming pool with two lounge chairs, surrounded by trees and a mountainous landscape.

1. La Posada Mountain Retreat in the Heart of Puerto Rico with Exceptional Views

Utuado

A G.

A modern entryway with a metal gate, a glass door, and a concrete floor.

2. Puerto Rico vacation dream house

Santurce

"Pictures are deceptive….sofa stains, kitchen ceiling cracks, bathrooms super small, not clean (a roach crawled on the arm of one of our guests while using the bathroom) pool was not cleaned and it took three days into our stay before someone came out to clean it, television wasn’t working in one of the bedrooms, there was no hot water in 4 of the bathrooms until the 4th day into stay and on the last 2 days there was no running water therefore we had to purchase several gallons of water to wash...

GGI C.

A white building with a number '20' sign, a tiled entrance, and potted plants.

3. Coastal Comfort: Spanish Villa Steps from the Sand

Santurce

Chris T.

A spacious living area with a large dining table, a sofa, and a view of a swimming pool.

4. Spacious 3BR Bungalow with Pool and Garden

Cap Cana

Marvin l.

A two-story building with a curved roof, large windows, and a balcony.

5. Relaxing Chalet with beautiful Sunrises & Sunsets!

Río Piedras

Lorena D

includes taxes & fees

23 Oct - 24 Oct

A balcony with white furniture, a potted plant, and a view of a modern building.

6. New Modern 3Bed 3.5 Bath Townhome #14

Grace Bay

zhannet n.

A pool area with two Adirondack chairs, a hammock, and a view of the ocean.

7. CASA ROARK OCEAN FRONT CHALET

Vega Baja

Ronald W.

A covered outdoor seating area with blue cushions and a round table, overlooking a scenic view with palm trees and the ocean.

8. Nos Soño Stay and Dive, holidays in paradise! Guest home

Sabana Westpunt

Elaine G.

A view of a coastal area with a wooden fence, dense green foliage, and a stop sign in the background.

9. Fabulous Rustic Chalet Beach House Across the Street From Beach on Grand Turk

Grand Turk

Latricia

A balcony with wicker furniture and two glasses of wine, overlooking a lush green landscape with mountains.

10. Grand Chalet, Private Pool, AC, River Access, Pool Table BBQ WIFI Parking

Rio Grande

Amy Y.

A pathway leading through a wooden door into a garden with a tiled floor.

11. Casa Campo Obymar, Panoramic Villa with private pool. Electric generator

Moca

Marilyn P.

A rustic outdoor cooking area with a chimney, a red roof, and a stone pathway.

12. Riverfront Home Perfect for Groups in the Middle of the Mountains

Vallejito Abajo

includes taxes & fees

28 Sept - 29 Sept

A two-story building with a blue exterior and a staircase leading to the upper floor.

13. Cayo Caracoles at Guayacan Guest House

Lajas

Amalia S.

includes taxes & fees

27 Sept - 28 Sept

A modern building with a blue exterior, large windows, and a small outdoor seating area with chairs and a table.

14. Luxurious and Cozy chalet close to Playa Buye to disconnect from everything!

Cabo Rojo

NOZOMI D.

A wooden deck with a pool, lounge chairs, and a table with a vase and glasses.

15. Spacious Creole cottage with private pool

Goyave

Eric R.

A two-story building with a white fence and palm trees in front.

16. Anci’s Villa 2nd Floor

Cabo Rojo

juan c.

A balcony with two white chairs and a red railing overlooking a hilly landscape during sunset.

17. La Loma: Cozy Retreat with Jacuzzi & Views

Cidra

includes taxes & fees

30 Sept - 1 Oct

18. Luxury Townhome Villa in Grace Bay - Seascape #16

Grace Bay

Robin S.

An aerial view of a resort with a large swimming pool, a basketball court, and a small children's play area.

19. Arcadia Caribbean Village

Barrabás

"As a person who like to do reviews I will tell you something; this place is above and beyond of what is showing in the pictures online. As a father I will tell you how happy I am to come here and celebrate my daughter bday, it is a place with everything that you need to have a great time with your family.The host is pretty amazing as well, I am mesmerized by the beauty of the place and how comfortable it is. 10/10"

David S.

includes taxes & fees

27 Sept - 28 Sept