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Find Chalets in Caribbean from $209

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Top Cities in Caribbean

Condado Beach which includes general coastal views and a coastal town

San Juan

Our top choices for Caribbean chalets

2 bedrooms, iron/ironing board, WiFi, bed sheets

Relaxing Chalet with beautiful Sunrises & Sunsets!

Río Piedras

10.0 out of 10, Exceptional, (49)

10/10

Exceptional

(49)

"Amazing spot to stay in especially if you have kids."

Laila S.

$197 nightly

The price is $209

$209 total

Dec 30 - Dec 31

Total with taxes and fees

Relaxing Chalet with beautiful Sunrises & Sunsets!

Guayacan Guest House @ La Parguera - Cayo Caracoles

Lajas

9.4 out of 10, Exceptional, (13)

9.4/10

Exceptional

(13)

"Absolutely great place, walking distance to everything. Loved the place as its perfect for large groups!"

edowilda

$292 nightly

The price is $310

$310 total

Dec 21 - Dec 22

Total with taxes and fees

Guayacan Guest House @ La Parguera - Cayo Caracoles

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

Utuado

9.8 out of 10, Exceptional, (34)

9.8/10

Exceptional

(34)

"Great mountain location "

Dale M.

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

Comfort Cottage, 2 Bedrooms, Air conditioning, Garden View | Terrace/patio

Comfort Cottage, 2 Bedrooms, Air conditioning, Garden View | Private kitchen

Cottage 15 Village de la Pointe

Le Vauclin

Cottage 15 Village de la Pointe

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

Rio Grande

9.0 out of 10, Wonderful, (9)

9.0/10

Wonderful

(9)

"Place was amazing"

Michael F.

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

3 bedrooms, desk, iron/ironing board, free WiFi

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

Moca

8.8 out of 10, Excellent, (5)

8.8/10

Excellent

(5)

"It was great! Loved watching the views from the terrace!"

Ana L. V.

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

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

Cabo Rojo

9.8 out of 10, Exceptional, (6)

9.8/10

Exceptional

(6)

"It’s situated in a walking distance to one of the gorgeous beaches on the island, playa Buyé.The facility felt safe, and the host Miguel was super accommodating.I would definitely recommend this place and plan on going back. "

NOZOMI D.

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

Anci’s Villa 2nd Floor

Cabo Rojo

10.0 out of 10, Exceptional, (2)

10/10

Exceptional

(2)

"When we enter the property, everything was vey nice and clean , decor awesome, beds comfortable, very close to the beach, Host Mery is wonderful, we had everything we need plus extra, wifi very strong, over all we had excellent stay!!!"

juan c.

Anci’s Villa 2nd Floor

4 bedrooms, desk, iron/ironing board, free WiFi

CASA ROARK OCEAN FRONT CHALET

3.0 star property

Vega Baja

10.0 out of 10, Exceptional, (11)

10/10

Exceptional

(11)

"Location was amazing, the host was very responsive and provided us with some great local recommendations. Absolutely recommend!"

Magdy a.

CASA ROARK OCEAN FRONT CHALET

1 bedroom, desk, iron/ironing board, WiFi

Beach nearby, sun loungers, beach towels

LaLolitaVilla - Steps away from Playa Buye!

Cabo Rojo

LaLolitaVilla - Steps away from Playa Buye!

Chalen-charmante Villa Créole aux Portes du Grand Sud de la Martinique

sainte anne

8.2 out of 10, Very Good, (11)

8.2/10

Very Good

(11)

"malgré un voisinage parfois bruyant"

antoine g.

Chalen-charmante Villa Créole aux Portes du Grand Sud de la Martinique

1 bedroom, desk, iron/ironing board, free WiFi

Ocean view romantic getaway chalet

Isabela

8.0 out of 10, Very Good, (1)

8.0/10

Very Good

(1)

$404 nightly

The price is $429

$429 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

Ocean view romantic getaway chalet

Fridge, microwave, stovetop, coffee/tea maker

3-bedroom chalet in amazing Combate, Cabo Rojo with WiFi, AC, pool, billard

Sector El Combate Cabo Rojo

10.0 out of 10, Exceptional, (1)

10/10

Exceptional

(1)

"Wonderfull place "

Andy C.

3-bedroom chalet in amazing Combate, Cabo Rojo with WiFi, AC, pool, billard

Oven, stovetop, dishwasher, cookware/dishes/utensils

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

Sabana Westpunt

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

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

Grand Turk

9.6 out of 10, Exceptional, (23)

9.6/10

Exceptional

(23)

"House was just as described! Close to beach and eating areas "

Latricia

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

The Heaven Villa, cerca playa dorada, a 30 Seg. de Fun City, 10 Mits aeropuerto

Puerto Plata

The Heaven Villa, cerca playa dorada, a 30 Seg. de Fun City, 10 Mits aeropuerto

2 bedrooms, in-room safe, iron/ironing board, free WiFi

Two Bedroom Villa, Long Bay, Providenciales - Eden House

Long Bay

10.0 out of 10, Exceptional, (23)

10/10

Exceptional

(23)

"The hosts (Jason and Leslie) are local and very attentive. Jason met us at the property to show us around and explain everything. He is also available 24/7 via text or call to answer any questions. Very clean property with a stocked kitchen, outdoor grill, pristine pool, and nice bathrooms and bedrooms. Highly recommend. "

Cody F.

Two Bedroom Villa, Long Bay, Providenciales - Eden House

2 bedrooms, iron/ironing board, free WiFi, bed sheets

Beachside Corail

Sainte-Anne

10.0 out of 10, Exceptional, (11)

10/10

Exceptional

(11)

"Merci á Laura et Nathalie pour le service et l’accueil. Nous avons passé une superbe semaine dans cette jolie maison à Saint-Anne. Grace à vous et aux propriétaires nous sommes revenus avec des souvenirs magiques ! La maison était exceptionnel. Rien à dire tout était parfait !"

Audrey

Beachside Corail

Fridge, stovetop, coffee/tea maker, electric kettle

Coastal Comfort: Spanish Villa Steps from the Sand

Santurce

10.0 out of 10, Exceptional, (2)

10/10

Exceptional

(2)

"We had a great time! property was beautiful and one minute from the water. Lots of extras like chairs, beach towels, dishes, games, sunscreen and all kinds of stuff that saved us trips to Walgreens. Loved it and will book again. "

Carlos M.

Coastal Comfort: Spanish Villa Steps from the Sand

3 Bedroom Villa Close to Long Bay Beach - Hampshire House

Long Bay

10.0 out of 10, Exceptional, (23)

10/10

Exceptional

(23)

"We really enjoyed the home, pool and location. It was perfect for our family and had everything we needed. We were close to everything and had a wonderful time. "

BreAnne G.

3 Bedroom Villa Close to Long Bay Beach - Hampshire House

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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