Guesthouses Caribbean

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289 guest houses

The Inn at Great Bay. Treasure Beach Jamaica

Treasure Beach guest house

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 20

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Price per night from

$861

JSH LETTINGS

Runaway Bay guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$158

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Secluded Sunsets waterfront w/pool- 1 Bdrm 1rst Fl

West End guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$173

LA MAISON, an exclusive guesthouse in Las Terrenas

Las Terrenas guest house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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$155

Newly Renovated, Quiet, Private Apt. near Airport

Nassau guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$86

Villa by the Cove

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$287

PalacetedelVedado Cuba

Dover villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$492

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$217

Carolina Point Resort -Studio Apartment 1 - close to Pigeon Point Beach Tobago

Crown Point guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 8 minutes

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$92

Responds fast! avg. 3 hours 5 minutes

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Price per night from

$240

3BD Villa Including Housekeeper/ Airport Transfers

St. Ann's Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$207

Tropical and Secluded Studio Casita

Noord apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$274

3 BEDROOM, 2 BATH LUXURY PH BEACH/GOLF CONDO Playa Dorada San Marino Residences

Puerto Plata apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful time in Playa Dorada” We stayed in Playa Dorada for the month of March 2014 and we really enjoyed it. I have travel a lot and stayed in many different hotel and condos, but this was the best. What you see on the internet, is the absolute truth. Cindy is a very honest and caring owner. I did have a couple minor issues during my stay, but they were quickly handle after I contacted Cindy. The condo is fantastic with very nice and comfortable furnitures and TVs, and the kitchen is ultra modern. We also really appreciated the outdoor BBQ (a very big and nice BBQ). The San Marino complexe is very nice and secure. The swimming pool is big and clean and the beach is only a five minutes walk from the condo, and at the beach you have very nice chairs and umbrellas. The staff at San Marino is excellent, the laundry service is great and not expensive. The condo is only ten minutes to Puerto Plata by taxi where you have the Las Sirenas store which is just like a WalMart (this is where we when for grocery shopping) they also have a Domino's Pizza. I visited the old San Felipe Fort, I went to the top of the mountain in the teleferic and had a really great time visiting many places around Puerto Plata. The only thing missing as far as I am concern, is something like a seven eleven in the plaza in the front of the condo. They have many things, but not your basic like bread, cold meat, butter and eggs. Beside that, they have many things. With all the condos being built around Playa Dorada, maybe someone will invest in a seven eleven or something like that. Beside that, everything was excellent, and God willing, I will go back next year.

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Price per night from

$259

3 BEDROOM, 3 BATH PH Luxury Beach/Golf Condo Playa Dorada San Marino Residences

Puerto Plata apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

“Perfect For a Family. Best Owner Hospitality! Great for Cooking” Newly renovated. We have 3 teenagers who need their own space. Everyone had their own beds and we had the entire penthouse suite to ourselves! Kitchen was beautiful and functional. Everything you need. Since it's a penthouse there is a large balcony facing out (with trees). Every day we ate all our meals, read books and at night played games out there. Weather is nice even in the evening or in the rain. Never used the inside table for eating. Since the bathrooms' sink separate; it's multi-user without waiting. This property was quiet and safe. We travel a lot and felt a lot more safe here than Mexico; travelling with teens... Cindy was the best owner I have ever encountered and we rent often. With Wi-Fi at the center of the complex, free messaging worked great. She provided so much information and help. Since she speaks 2 languages, she would call the front desk and arrange anything. I have a bad medical condition and since our King bed was hurting bad, she had a bed topper shipped immediately at her expense! So now vacationers have 2 choices. Since 1/2 her family is local, she arranged many trustworthy excursions from her U.S. home. She arranged a great driver at reasonable cost in a superbly clean Honda van (we are too big for a car). Believe me, after a few other taxi rides, he's a safer driver and spoke decent English for local info. The beach was pristine and not too busy. We walked a long way on both sides and this is the most protected from winds, less busy and with an open restaurant/ bar right there. Also since many locals own in this resort, not too many venders bother this area! Are the pictures accurate? No. It's actually nicer than it shows. Really! Proximity to everything is nice. Short taxi rides to a Walmart type supermarket and a lot of attractions. Taxis at the gate hose you. Use Cindy or recommendations from other owners in the resort for transport. Cindy also gave us a valuable restaurant list. She is very organized. Great 14 day vacation!

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$259

OCEANFRONT CONDO, SERENE, UNCROWDED GENTLE WINDS

Christiansted apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$316

Out of the Blue Villa

Treasure Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,148

Hacienda Los Guayacanes private secluded Beachfront

Dominican Republic villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“We called it Paradise!” The place was AMAZING. The pictures online are awesome; the place in real life is breathtaking. The house is small. Two tiny bedrooms, one with a full(?) sized bed in it and the other with two twins. There's a little living room with a futon. A small bathroom inside and then the gorgeous outdoor bathroom attached to the master bedroom. I've never been in an outdoor bathroom before but it was crazy cool...especially at night when you light the candles! The house itself is very tastefully decorated. It has a beachy/nautical theme, but not gaudy, just perfect. Don't worry about the smallness of the house, though, because you seriously won't spend any time inside. The whole property is designed for the guests to be outside. We spent a ton of time on the blue outdoor couches, watching our 5 year old in the pool with the ocean in the background and listening to the waves or the music from the sonos system (an awesome touch!). Hilda, Euris and Papo are great. Hilda makes the best food and even taught me how to make flan (I recommend asking her to make that). Euris is so easy to be around. He drove us to the Parque Nacional Jaragua. My husband, who speaks Spanish, learned a lot about the area from him. They got along great! Papo kept the pool clean for our daughter and even tolerated her "helping" him. He spends a lot of time keeping the grounds looking so great. And his bonfires are the biggest we'd ever seen. We like our privacy and we're a little worried about having staff around all the time, but all three were so friendly and unobtrusive that it felt like a true paradise. When we booked the house we had planned for it to be just me, my husband and our daughter. Our in-laws were with us for the first part of our vacation and then we had planned to split up for our stay at Las Guayacanes but due to some miscommunication, they were without a place to stay for the first night. We invited them to stay with us until their place in Santo Domingo was ready. They ended up staying two nights (even though they were paying for a hotel room in the capital) because the property was so great. Euris drove them into the city when they were ready to leave. A few days later we decided to drive into the city to visit with them and invited them back to paradise for our last two nights . Again they agreed whilst still having to pay for their hotel room in the city(again). That's how great the place is!!! Also Edmundo is a great host. He responses are very quick and he'll readily answer any questions you have. He's done a great job with the rental. It's fantastic.

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$344

Pimento Oasis, Ocho Rios, St. Ann, Jamaica

Ocho Rios house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$224

2-br watervu apt-Seawind onthe Bay,Montego Bay,Jam

Montego Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$213

carib apartments mahogany beach ocho rios

Ocho Rios apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$87

Westin St. John 3 Bdrm/ 3 Bath Thanksgiving Week

Cruz Bay villa

  • 4 bathrooms
  • sleeps 10

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$987

3 BD VILLA INCLUDES HOUSEKEEPER/AIRPORT TRANSFERS

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$276

Intimate Aruban Two Bedroom Casita

Noord apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$428

Island Treasure Villas

Ocho Rios house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great, beautiful villa with a great owner!!!!” The villa was just as beautiful as the pictures!! Also there was a miscommunication with the number of guests and the owner was very understanding and handled it promptly. He was very nice and was available when needed. I would recommend this villa 100%!!!

Responds fast! avg. 1 hour 13 minutes

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Price per night from

$138

The Bird House

Juan Dolio villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$517

OCEAN FRONT - Taino Beach - Private Resort!

Freeport hotel apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

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$165

St Croix, U.S. Virgin Island Condo Near the Beach

Frederiksted townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$86

Barrero Beach Hideaway Apartment

Rincon apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Right on the Money” Spent a week here last year on a vacation from our home in St. Croix. My wife and I loved it. Great location right on the beautiful beach in a great local neighborhood. Fish market and bar next door and I rode the neighbors horse through the streets on Sunday afternoon. Really an amazing place.

Responds fast! avg. 1 hour 55 minutes

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Price per night from

$127

Sun & Sand Beach Condo with Wifi ( Sleeps 4 )

Ocho Rios apartment

  • 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.

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$114

Rainbow Beach Apts. 2 BR, Ocean View with Balcony

Calibishie apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$109

Calibishie Sandbar Ocean View

Calibishie guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$103

Harmonie Creole B&B - Orange Room - Sea View

Bouillante guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$98

Your Family wants a Magical Christmas - On a Beach!

Bavaro villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$316

Mountain Paradise Rancho Rio Alegre In Dominican Rep

Monsenor Nouel Province house

  • 17 bedrooms
  • 15 bathrooms
  • sleeps 40

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$1,378

Sandcastle Resort - Seaview STUDIO apartment

Ocho Rios studio

  • Studio
  • 1 bathroom
  • sleeps 3

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$94

Simon Says Grand View Villa

Choiseul guest house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

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Price per night from

$92

Roadrunner Bonaire - Kralendijk

Kralendijk guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$155

Jaca Paradise Villa at The Palms Ocho Rios St. Ann

Ocho Rios villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$287

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