Chalets Caribbean

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366 chalets

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Port Royal chalet

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 3 match: Fireplace, Shared indoor pool, Rental types

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Price per night from

$246

Happy Trees, Sandy Lane, St. James, Barbados

Sunset Crest villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$3,400

On the beach

Saint Francois studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 3 match: Rental types, Fireplace, Shared indoor pool

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Price per night from

$68

Strathairn116

Kingston house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$97

F3 sea Guadeloupe Deshaies Villa 4-6 pers 6232

Deshaies apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Fireplace, Shared indoor pool

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Price per night from

$161

Dreamcatcher - luxury villa, stunning views over turquoise seas

Shoal Bay Village villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$945

Luxury Oceanfront Villa for Rent

Las Galeras villa

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$287

Relax in paradise

Las Terrenas apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$172

Le Parc aux Orchidées, cottage Thunbergia

Pointe-Noire chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 3 match: Fireplace, Shared indoor pool, Rental types

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Price per night from

$117

SANDYLINE... The Essence of Luxury! 2 Heated Pools, Jacuzzi, Tennis, Gym, Chef!

Terres Basses villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$5,214

BEACHFRONT,QUIET, BEAUTIFUL LANDSCAPE

Rio Grande apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$218

Oasis at The Cliff in Cupecoy -Oceanfront Luxury

Cupecoy Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Fireplace, Shared indoor pool

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Price per night from

$303

Le Parc aux Orchidees, cottage Liane de Jade

Pointe-Noire chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Fireplace, Shared indoor pool, Rental types

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Price per night from

$150

Paradise Creek Cottages with Van.

Andros Town cottage

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$457

Hammock Studios; just 1 minute from one of the best beaches on Bonaire!

Belnem apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 24 minutes

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$77

carib apartments mahogany beach ocho rios

Ocho Rios apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$87

Bungalow natura village

Sosua chalet

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“relaxation and well-being” The time spent in Bungalows Natura Village was great. It was wonderful to wake up in the morning with birdsong. The garden is beautyfulas is the pool. The owners are very nice and available for any need/suggestion. 2 very nice beaches within 5 minutes walking distance. The fruit smoothies are wonderful. I have to return there soon!

1 of 3 match: Fireplace, Shared indoor pool, Rental types

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Price per night from

$73

Romantic Caribbean Get Away.

Parlatuvier chalet

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 3 match: Fireplace, Shared indoor pool, Rental types

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Price per night from

$155

Gîte de standing classé 4* au pied du parc nation

Saint-Claude chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 3 match: Fireplace, Shared indoor pool, Rental types

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Price per night from

$124

The Old Fort Estate

Mount Pleasant villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$1,571

Teresina

St. Ann's Bay chalet

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Fireplace, Shared indoor pool, Rental types

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Price per night from

$201

Shipwatchers Studio with Mezzanine, Your Oceanfront Holiday Home!

Ocho Rios studio

  • Studio
  • 1 bathroom
  • sleeps 2

“Perfect!” Our stay at afiba View was simply perfect. The sea on one side of house and a private pool on the other. What else could you ask for? Oh yeah, and there's an amazing sun deck with walk out snorkeling in a private little cove! Once you figure out the route taxi, which takes about 2 seconds, you're free to go anywhere along the coast of Jamaica for about $1.25. I cannot recommend this villa enough. Sade is a wonderful host who answered all of my questions and made sure we enjoyed paradise as much as possible. This was our second trip to afiba and we're already trying to figure out when we can return. Can't wait!

1 of 3 match: Rental types, Fireplace, Shared indoor pool

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Price per night from

$126

“Escape from reality” My husband and I both have high-pressure jobs. We were looking for an escape from the grind. We found it at Water's Edge. As we entered the gate of this quaint island paradise reality melted away. The main living area is open and comfortable. The bedrooms are spacious. But I can't say that we spent much time in the house... The view from the back patio is breathtaking. The doors open to a beautiful outdoor living space which overlooks the Caribbean. We ate breakfast, lunch and dinner outside! The days were lazy, filled with much needed R&R.; We read books, napped in the hammock, and simply enjoyed the sun and the seascape. The home has direct access to the water, and the pool is perfect for that quick dip to cool off. Although we were looking for a quiet getaway, nightlife was not far away. We found it easy to get over to Paradise Island for some dinner and gambling at atlantis. We enjoyed our trip so much we returned with our daughter the following year. She enjoyed it as much as we did. We've got a new baby at home, but are looking forward to getting back to Water's Edge soon.

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$916

LIGHTHOUSE 6B... penthouse with spectacular views, resort amenities of OBBR

Oyster Pond condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Fireplace, Shared indoor pool

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Price per night from

$360

Domaine Lizardy

Pointe-Noire chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Relax and Pleasure” A very nice place to relax watching the sunset, in the wild part of Guadalupe.

1 of 3 match: Fireplace, Shared indoor pool, Rental types

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Price per night from

$124

Harmony Villa Dominica 3 Bedroom

Morne Trois Pitons National Park villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“Beutiful, island with very frienly people, unspoilt by tourism.” An excellent holiday, all members of the party really enjoyed the villa and the island, very friendly staff, who were fantastic.

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$373

White Seagull -Just For Two- POOL SALE NOW

Cruz Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Spectacular View and Wonderful Hospitality!” We just returned from a wonderful 8-day stay in the White Seagull, at "Just For Two" on St. John. This was a return trip for us, having stayed there, last May, as well. We rarely return to the same location, preferring to seek new adventures. This was a rare exception and a testimony to the wonder of this place - both St. John and Jacqueline's hospitality. The room is wonderfully decorated and comfortable, with 270 degree views of the Caribbean. We overlook Great Cruz Bay and Chocolate Hole from our windows, with views of St. Thomas from the Sky Lounge. It's amazing to wake to the early sunrise and see the ocean view, by simply sitting up in the bed. We took wonderful photos of the sunsets from the rooftop Sky Lounge and our location near the top of a mountain, overlooking the island. Jacqueline readily gave us access to her private patio, as well, providing wonderful views of Great Cruz Bay and relaxing surroundings to talk or simply play cards, in paradise! The room is well decorated with antiques and personal items. There was good Wi-Fi access and a TV with limited channels, but we rarely used them. A fireplace was available, but we can't imagine using it, except in the dead of "winter"! The room offers a small kitchenette, suitable for simple breakfasts or lunch preparation. There is access to a grill in the courtyard, as well. However, we mostly enjoyed the wonderful food at all the restaurants on the island. You definitely need to rent a car and we have had great experience with Courtesy Rental. The roads are steep, somewhat narrow and you get the challenge of driving on the left side. It's a challenge, but quickly becomes comfortable. The roads Just For Two are steep, but enjoyable. There is a back way that allows a "less steep" option, if it is rainy. Next year is our 25th anniversary and we are planning to return, yet again. It's hard to argue with perfection - especially for a milestone date.

Responds fast! avg. 3 hours 17 minutes

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$602

The Old Fort

Mount Pleasant fort

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$1,177

Strathairn110

Kingston house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Sweet deal!” This vacation rental is cozy, comfortable, affordable, safe, and boasts a great location. I have stayed here on two separate occasions. Perfect place to stay!

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$97

expectacular apartamento en la zona residencial de santo domingo

Santo Domingo apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Fireplace, Shared indoor pool

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Price per night from

$69

Private Chalet Ocho Rios

Tower Isle chalet

  • 1 bathroom
  • sleeps 2

1 of 3 match: Fireplace, Shared indoor pool, Rental types

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Price per night from

$58

Charming Country Cottage with panoramic views

Mandeville b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$344

Ocho Rios Beach-front Resort Condo-WiFi

Ocho Rios condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Location yes! housekeeping staff no...” Hello, we just came back from a week in Ocho Rios and had a fantastic time. The condo we rented was not in the tower shown in the picture but in the adjacent hotel, which was good too. And yes, location in great. Right next to a nice beach with a pool in the complex. So, as I mentioned, location was great. However, housekeeping left to be desired. We were told that the condo would be cleaned every 2 days, but after 3 days, no one had come to bring fresh towels or toilet paper! We had to call and call to get some service. Also, when we asked for some dishwashing soap, we were told to use either hand soap or soap for clothes. So aside from the little hickups with the housekeeping staff, I would recommend this rental.

1 of 3 match: Rental types, Fireplace, Shared indoor pool

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Price per night from

$69

Pitaya

Pointe-Noire chalet

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 3 match: Fireplace, Shared indoor pool, Rental types

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Price per night from

$154

Residence FRESH WAVE

Sainte-Luce apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$173

THE CLIFF

Cupecoy Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 minutes

1 of 3 match: Rental types, Fireplace, Shared indoor pool

1 of 3 filters match

Price per night from

$344

Beach Chalet

Rio San Juan chalet

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 3 match: Fireplace, Shared indoor pool, Rental types

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Price per night from

$252

Bonao Summer Villa Retreat

Bonao villa

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 3 match: Rental types, Shared indoor pool, Fireplace

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Price per night from

$144

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