Chalets Caribbean

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660 chalets

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Villa Gemma, Eco-Friendly Residence

Las Galeras house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$115

Escape Winter at Westin St. John Resort, USVI

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$2,004

Blue Moon, Saint Lucia - Ocean View, private pools

Cap Estate villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$676

TEST PROPERTY

Port Royal chalet

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 3 match: Games room, Shared indoor pool, Rental types

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Price per night from

$246

Lifestyle Resorts Crown Villas

Puerto Plata villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$287

On the beach

Saint Francois studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 3 match: Rental types, Games room, Shared indoor pool

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Price per night from

$68

NEGRIL HOTEL LUXURY BOUTIQUE

Negril villa

  • 11 bedrooms
  • 13 bathrooms
  • sleeps 24

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$81

Pleasant apartment 10 minutes from the beach

Sainte-Anne apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$49

Villa by the Cove

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$287

PalacetedelVedado Cuba

Dover villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$491

F3 sea Guadeloupe Deshaies Villa 4-6 pers 6232

Deshaies apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Games room, Shared indoor pool

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Price per night from

$160

Sandcastle

Noord house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$401

JUNIOR SUITE (DREAM SUITES)

Santo Domingo condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$138

Tropical Vacation Villa, Ocho Rios

Ocho Rios house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$229

Villa Giada, Eco-Friendly Residence

Las Galeras villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$92

Exclusive ViP Junior Suite

Puerto Plata private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$126

Le Parc aux Orchidées, cottage Thunbergia

Pointe-Noire chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 3 match: Games room, Shared indoor pool, Rental types

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Price per night from

$117

Sweet Wind Villa overlooking Hurricane Hole

Coral Bay house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Sweet Wind is outstanding” We just returned from 9 wonderful days at Nina"s Sweet Wind Villa. The view is spectacular, the trade winds always kept the villa very comfortable and the location to great snorkeling and beautiful beaches is a big plus. Nina is a great hostess and close by if you need any hints on where to go or places to eat but she is never in the way. She even was so kind to fillet a Mahi Mahi I bought in Cruz Bay!! The "Pod" set up of the Villa makes it really nice. The living, dinning and kitchen area is separate but right next to two pods that are the sleeping and bathroom areas. Great for 3 couples or a family. The East end of the Island is also very peaceful and quiet. We certainly plan to return.

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$686

2024 Atlantis Harborside 1, 2 or 3BR top fl. waterfront - 11/02/24 to 11/09/24

Paradise Island villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$409

Casa Phil Ocean View Modern Luxury Family Friendly

Las Terrenas villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Highly recommended” We spent the week of New Year's 2013/14 enjoying Casa Phil. The house is exactly as described, and the photos accurately reflect Philippe's beautiful home. The home is closely located to the beach, actually a 5 minute walk. We enjoyed running on the beach daily, as the beach extended for many miles. On this beach, there are a lot of restaurants and bars which we enjoyed as well. Philippe is a very gracious host. He was extremely helpful in arranging all of our transportation needs, from taxis to and from the airport, to renting dune buggies (which he builds himself), and a quad. He was always checking in on us as well, making sure that everything was ok, and whether or not we needed anything. We can't thank Philippe enough for making our vacation so memorable. We highly recommend Casa Phil to anyone interested in a vacation in Las Terrenas, DR.

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$675

Rum and Kai - Beachfront Bliss 7th Night Free

Rum Point apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Favorite place ever!” We have done a great deal of traveling and have rented several homes through vrbo. Matt & Tracey's condo is by far the best vacation spot ever! Their home is fully equipped with everything necessary for a comfortable stay and then some! The location affords privacy and the local beach next door is steps away if you are looking for a little action. The snorkeling is outstanding and the beach is by far the most beautiful we have seen! Matt & Tracey's place is definitely #1 on our list of favorite vacation spots and we hope to return soon!

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$281

Calypso Condo, Luxury on the Water at Gentle Winds

Christiansted apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Calypso condo stay was paradise!!!” We recently returned from a weeks vacation to St. Croix where we stayed at Calypso Condo C-2 in the gated community of Gentle Winds and had a fabulous time!!! The condo was immaculate upon arrival and Angela, the unit manager, stocked us with some groceries I requested so we didn't have to go out at night when we first arrived. There were six of us and with the three bedrooms, three bathrooms, three balconies and the loft area we did not feel crowded. Barbara, the owner, thought of everything to make our stay enjoyable and a home away from home. The book Life in the Left Lane, the bottle of champagne in the fridge, the starfish necklaces and the gift certificate to the Snack shack were complimentary gifts to us for staying there. It was a vey nice finishing touch by Barbara and very much appreciated. The kitchen was very well-equipped. There were so many books, Wii games, VHS movies, DVDs, and board games for all ages to choose from. It was nice having a grill to cookout on since we don't always like to eat out and as we found out food in St. Croix is expensive. I would definitely come back to St. Croix and stay at Calypso Condo again in a heartbeat !!!! The view was breathtaking, the beach gorgeous and the pool refreshing. The grounds at Gentle Winds were beautifully kept and the people there including the guard, the groundskeepers, and the woman who ran the Snack Shack were very polite. Staying there in early June had its benefits. I truly felt we had the whole place to ourselves. Besides us there were maybe 6 units out of 65 that were occupied at the time. No fighting for chaise lounges at the beach or pool.. A nice perk of the off season. Before leaving for St. Croix Barbara made sure we had directions from the airport to the condo and how to access the lockbox should the unit be locked. She also stressed checking out her website which had extremely helpful tips and suggestions one should know before arriving. I was also impressed that early on in our stay Barbara called and sent me an email checking in with us to see that everything was going well. We did so many fun activities while in St. Croix- stand up paddle boarding , snorkeling, kayaking, relaxing on the beach, shopping in Christiansted, touring the Cruzan Rum Factory, watching the sunset at Off the Wall restaurant while playing bingo and watching the sunrise at Point Udall. Needless to say we were all very sad to leave but have so many fond memories and beautiful pictures.

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$441

Máre ESJ Azul Tower 15th Floor Spectacular View

Carolina apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Great Downtime in San Juan” Unit was perfect for a getaway week in San Juan. We were on the beach every day which provided warm water, sun, and shade. Condo was perfect size for us, and on 15th floor very safe, quiet, and private. Had everything we needed, washer-dryer, etc. Building employees very courteous and helpful. Variety of restaurants and supermarket within walking distance. We did not have to rent a car. We ate breakfast and lunch in condo, then ate dinner out every day. Pool deck is beautiful and health club a big plus. Overall great place to relax, chill out, and enjoy the ambiance.

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$286

BEACH FRONT PROPERTY! 6 Bedroom on Grace Bay Beach ,Sleeps 12

Grace Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

“What an awesome Place!” Top notch place to stay, every imaginable amenity, incredible white sand beach out your back doorstep. Incredible landscaping throughout the entire property. Long back patio overlooking the pool and beach. What a great place for the entire family to hang out and relax and the best beds I have ever slept in. I highly recommend!

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$5,038

OCEANFRONT CONDO, SERENE, UNCROWDED GENTLE WINDS

Christiansted apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$315

Oasis at The Cliff in Cupecoy -Oceanfront Luxury

Cupecoy Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Games room, Shared indoor pool

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Price per night from

$303

“Amazing family vacation! Sunset Point paradise” Wow! Where do we start? We just enjoyed an amazing week at sunset point villa. It is a piece of paradise and a slice of heaven. We loved it so much. The villa is beautiful. While the pictures and description are nice, they can't do full justice to the experience. Our stay was nothing short of superior. Prior to our arrival Bob was very attentive, always answering email questions quickly. The service was wonderful too. We were welcomed by Julian and he gave us a great introduction to the villa as well as the island and all it has to offer. We loved all the added touches! The villa has so much available for a family vacation. It was the perfect set up for our family. We have four children ages 15,13,12 and 10 and they all loved it! The pool toys and raft are great and were put to immediate use. The extra touches upon arrival made out hearts warm and made us feel so welcome. We rented kayaks and stand up paddle boards and we enjoyed using them right off the dock. We also chartered a boat and enjoyed a day of exploring and wake boarding with Nautique sports. Sam and Jake were awesome and the kids loved the adventure. The location of the villa is great too. Taylor Bay beach is so beautiful and we loved swimming over to play on the beach. The sand is so pristine. Another bonus were the two nice tennis courts. We had many family matches on those courts. We hope to have the chance to return to the amazing Sunset Point Villa.

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$1,134

Luxurious Ocho Rios Waterfront Villa: Private Pool, BBQ, Chef, Nr. Attractions

Tower Isle villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 16

“My stay here was heaven on earth.” My stay on this villa was great. Everything I could imagine and more Food was delicious and authentic; not process or frozen. The master suit where I stayed was immaculate. The power shower to the huge jacuzzi bath. The king size bed made my night rest wonderful. It's felt like I was sleeping on clouds. This villa was hard for me to leave, from pool, xbox, board games and a fantastic pool why must I go outside.(lol). When I decided to go outside it was also a great and wonderful experience. I visited duns river falls, when to the hot spot night club margarita ville, oceans 11, and amnesia. We sang karaoke had great Jamaica drinks and watch the beautiful scenery. All these great attraction only 12mins tops from the villa. However my highlight of the stay is the private beach, only 2min walk from the villa. Great vacation I'm booking another stay for January andirons can't wait...

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$974

Private Family Vacation Home-4 bedroom-Gated Community

Arecibo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 3 match: Rental types, Games room, Shared indoor pool

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Price per night from

$207

The Carib House Turtle Bay Falmouth Antigua

Falmouth villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Always the best!” We are returning guests forthe last 9 years...do I have to say more?

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$974

Le Parc aux Orchidees, cottage Liane de Jade

Pointe-Noire chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Games room, Shared indoor pool, Rental types

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Price per night from

$149

Grendon House, Sandy Lane, St. James, Barbados

Sunset Crest villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$1,875

Pimento Oasis, Ocho Rios, St. Ann, Jamaica

Ocho Rios house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$224

Retreat Plantation House, near Negril, Jamaica

Negril villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Fantastic get-away outside of Negril proper” The Retreat Plantation House is a picturesque villa in "Retreat", Westmoreland Parish, situated on a hillside overlooking acres of sugar cane fields on what is a still operational plantation. Although at times the tranquil surroundings may transport you to another century, the villa is newly refurbished and replete with the necessities of modern living. The three bedrooms easily accommodate 7, and our large group of 9 was quite comfortable throughout our stay. If you are looking for a respite from the gauche touristy atmosphere of the all-inclusive resorts on 7 mile, then Retreat is ready to oblige with a more relaxed, authentic, local Jamaican feel. If your vacation contemplates forays into town and the beach, then Retreat is also well suited (it's a 15-20 min. cab ride to the action, at about $2 USD per person, day rate. Renting a car is also feasible).

1 of 3 match: Rental types, Shared indoor pool, Games room

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Price per night from

$115

GOLD Deluxe Suite @ Cap Cana Marina - Airport P/U

Punta Cana apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“A week of tropical relaxation!” Ivan, We have been home nearly 2 weeks now but find ourselves still thinking and talking about what a wonderful time we had. We found the condo exceptional. The attention to detail in the condo was impressive. That along with the beautiful view from the condo and the great location of the condo on the property made it truly seem like the perfect accommodation. A short 4 minute walk to the beach or another short 5-6 minute walk to the Mariner Restaurant and two larger pools. We cannot say enough about the staff of the Fishing Lodge. It seemed they went out of their way to anticipate our every need. Delicious food, entertainment, cleanliness, hospitality and excellent service along with the beauty of the condo and resort provided us with a very memorable vacation. We hope to visit again. Le and Roy 4/13/14

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Price per night from

$160

Honey Hill Villa at Anse la Roche, Carriacou

Carriacou Island villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$161

Amazing familiar villa caribbean style!!

Punta Cana villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

“We had a blast!! Great place to stay.” My friends and I stayed here for our first visit to Punta Cana. We had an absolute blast. Alfonso was very accmodating and he was extremely helpful to any and everything that we needed. Angela was great. She made us feel comfortable our entire stay. I would recommend this place to anyone. The rooms were nice and the pool is amazing. We will definitely me revisiting this place.

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Price per night from

$573

Westin St. John 3 Bdrm/ 3 Bath Thanksgiving Week

Cruz Bay villa

  • 4 bathrooms
  • sleeps 10

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Price per night from

$985

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