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Watersports Holidays in Caribbean - Holiday Lettings

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4,645 properties with watersports onsite or nearby

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Holiday log cabin in Caribbean

Maxwell log cabin

  • 1 bathroom
  • sleeps 2

from £33 / night

£211 - £244 / week

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Holiday home in Trinidad and Tobago

Crown Point house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £118 / night

£821 / week

1 / 38

St Martin / St Maarten holiday villa rental

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,273 / night

£8,910 / week

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Holiday apartment in Jamaica

Montego Bay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £65 / night

£453 / week

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Holiday villa in Curaçao

Willemstad villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £164 / night

£1,145 - £1,552 / week

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Villa accommodation in Caribbean with shared pool

Punta Cana villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

from £113 / night

£657 / week

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Holiday apartment with golf nearby in Caribbean

Humacao apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £169 / night

£1,501 - £2,158 / week

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Holiday home with golf nearby in Caribbean

Frigate Bay house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Relaxing! Memorable! Close to the Beach!” This villa is close to everything in the resort area- Frigate Bay. It is walking distance to the beach and close to the local strip which is filled with local restaurants. This villa is alot bigger than we thought, the rooms are huge. We all had a peaceful rest at nights. We hope to go back by the end of this year.

from £263 / night

£1,839 / week

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Holiday apartment with tennis court in Caribbean

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Wake up to beautiful ocean views and warm trade winds” My wife and I stayed in this studio for a week in early January 2014 and we were extremely pleased with every aspect. The owners are very responsive and friendly. When we arrived, the caretaker was awaiting our arrival with a smile and offered reserved parking and an efficient check in. Very friendly and happy to accomodate us in whatever we needed. When we walked in, there were no suprises, except the amazing view! The pictures are exact and the view in person is even better. Wi-fi and TV are good. Decoration and style is chic and European. Great use of space. Ac is good if you need it. The old vacated hotel building adds some romance to the grounds, and the small stores in Mont Vernon were a convenience, even though the Simply Market was an easy 5 minute drive. We found a new restaurant every night very close by, and every meal was delicious. The full service in-studio kitchen allowed us to eat breakfast and lunch in, enjoying the beach, then just dining out once a day in the evening for dinner. The pool is very nice, and the beach is irresistable. Short walk to dine, drink, and enjoy just down the beach. Everyone was very friendly and happy. All in all, we enjoyed this relaxing vacation and studio so much, we've already booked a stay next January.

from £71 / night

£460 - £920 / week

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Caribbean holiday villa rental

Mount Pleasant villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

from £1,607 / night

£11,247 / week

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Dominican Republic holiday home rental

Cabarete house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £227 / night

£1,595 / week

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Holiday hotel apartment with shared pool, tennis court in Caribbean

Noord hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £132 / night

£920 / week

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Apartment letting in Caribbean with golf nearby

Silver Sands apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“"Amazing Place to Hang Out"” We stayed at the White Coconut Studio for two weeks in February 2014. Prior this visit, we experienced beautiful Barbados during cruise visits. These one day visits encouraged us to step out of our cruise ship box and choose Barbados as our vacation destination. We looked on- line to find the perfect place to stay. We found the White Coconut Studio to be that place on the south coast of the island. We were not disappointed in anyway. The studio met all of our expectations, very clean, comfortable with all the amenities we needed. Stefano arranged to have us picked up at the airport which was a ten minute drive to Blue Ocean where Stefano greeted us and ensured we were comfortable with our new surroundings. The first week we decided to use the bus system and walk abouts within the south coast. A short 5- minute walk up the hill to catch the #11 bus. For walkers there is a path that goes past the Surfer Bar that leads to a coastal road, walking past beautiful homes that lead into Ostins it took approx. 45 minutes. In Ostins there is an IGa super market for all you grocery needs, and across the road there is the fresh fish market where you can buy fresh fish for your dinners. After our dinner at the studio we went to the Surfer's Bar and Grill, a 2 minute walk for evening cocktails. Sunday nights there was live music, a great place to hang out at the end of a day. Our second week, Stefano was so kind to arrange a car rental to be delivered to the studio and arrangements were made to take the car back to the airport for our departure. Stefano also put together a catamaran sail for the day on the west coast. Great time!!Elisabetta was so kind to change our bed linen and towels every few days allowing us to use the washing machine and clothes line and Wi-Fi. Thank-you Stefano and Elisabetta for a wonderful, quiet, safe, and secure home-base to experience an awesome Barbados vacation. Would love to come back and do it all over again. John and Sharon

from £66 / night

£460 - £920 / week

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Holiday home rental

Rincon house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £94 / night

£422 - £554 / week

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Holiday villa with shared pool, golf nearby in Caribbean

Frigate Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Amazing accomodations ..” I have stayed at Sealofts On The Beach several times and each time Susan and staff have made the experience a pleasant one. I am a Travel agent and Destination wedding planner and love the feel of being at home and in such a convenient location with a great price and view. I love the wireless internet, local cell phones and Magic Jack. The pool is amazing and you are only a short walk away from the beach. The units are well appointed and have everything you need to enjoy all that St. Kitts has to offer. Would highly recommend.

from £165 / night

£1,149 - £1,478 / week

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Holiday townhouse with shared pool in Caribbean

Frederiksted townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £71 / night

£493 - £624 / week

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Holiday apartment in Caribbean

Carolina apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £61 / night

£422 / week

1 / 10

Caribbean holiday villa rental

Jolly Harbour villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

“Excellent” The villa was exactly what was in the pictures, clean and spacious. The morning sunrise on the deck was magnificent , the sunsets are superb cant wait for my next vacation.

from £129 / night

£878 - £952 / week

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Caribbean holiday villa accommodation

Nevis villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £535 / night

£3,283 / week

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Holiday apartment in Puerto Rico

Carolina apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £61 / night

£427 / week

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Caribbean holiday cottage rental

Cayman Brac cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“Cayman Cottage: Home on the Blue Lagoon” If this is your first trip to the Brac, then Cayman Cottage is for you. We've been coming to the Brac for 10 years and love the serenity of the protected reef lagoon at the cottage. Many times the sea is too rough elsewhere to swim or snorkle, but you can always swim in the lagoon. We like having our morning coffee out on the beach beneath the palms and watching the sun come up. Many mornings we'll see baby turtles sticking up their heads and you'll always see more sea birds here. After a day in the sea, sun, and wind, you can relax in the "courtyard patio" in front of the cottage--there's a hammock beneath lush foliage and a table with chairs. You can go to a couple of restaurants on foot--as well as the liquor store. A grocery store is a short drive from here. Or you can explore the whole island from this cottage. Sue Smartt will be able to answer any questions you have or she will welcome you here and leave you alone to enjoy yourselves. The kitchen is very well-equipped if you have a mind to cook, as well. Many times of the year, you can turn your beach chair to the east and watch the sun rise over the sea and then at the end of the day, turn it to the west and watch the sun set, all from one spot. We recommend Cayman Cottage for your Brac vacation. Robin and Doug

from £141 / night

£985 / week

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Holiday home in Puerto Rico

Rincon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Heaven on Earth is right!” You have reached the end of your search. Paradise at last! Rick's family clearly loves this property and it shows in the way that he communicates with his renters and in the way that the house is set up. Our group had a bit of a snag with our vehicle breaking down, putting us into Rincon much later than we expected. Rick was so helpful in giving us directions as we drove to the house, and his warm and easy manner was so refreshing after such a long day! Once we arrived we were so glad to know that we made a good decision to stay at Casa Tres Hermanos. The house is beautiful and bright inside the living room, the bedrooms were decorated tastefully, the kitchen was well-stocked and information about the property was readily accessible. Later in town, we had an amazing dinner at La Copa Llena Restaurant at the Black Eagle, a must for drinks and tapas! While the house was just right, the real gem of this property was outdoors! Rick's family has chosen a stunning location to vacation. The beach is literally 20 steps out of the backdoor, with reefs just feet off of the shore. We spent an entire second day lazily exploring and snorkeling in the nearby waters. Our group saw plentiful lion-fish, urchins, eels, multicolored fan and brain coral, scores of tropical fish, multitudes of shells and a galaxy of beach glass. It was nice just to sit an relax as well. Thankfully we were able to do so because beach chairs were provided, of which we took full advantage. Also worth mentioning is the patio on the side of the house. This area allowed for us to have a very pleasant lunch without going far from the water, and later a dinner in the perfect night air with blended local fruit and rum as the order of the evening Directions to the center town could be a bit confusing at night, but with very little effort we were able to safely explore our way around. We will definitely be returning to Casa Tres Hermanos and we thank the Swales for a lovely stay!

from £230 / night

£1,806 / week

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St. Lucia holiday villa rental

Marigot Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

“Fantastic!” We would highly recommend staying at Bay View Villa. It is impeccable, clean and beautifully kept. All appliances and furnishing are first rate so you can move in a feel comfortable and at home — everything is very user friendly. Each bedroom has its own master bath suite, making for very private quarters. Cornelius and Pauline were extremely welcoming and helpful so you feel settled in and relaxed right away. They are also very responsive if you need anything. The house has incredible views of both the ocean side and the bay side. The gorgeous setting makes you want to just stay there and enjoy the views and all the activity in this sensationally beautiful harbor. The neighboring community is warm, friendly and helpful. Excellent local dining — we recommend the new Capella Restaurant right on the harbor — it is beautiful with superb service and cuisine.

from £277 / night

£1,940 - £5,306 / week

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Holiday home with swimming pool in Caribbean

Kralendijk house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“A wonderful week in Kas Jato Bako” What a wonderful week we had in Bonaire and in particular in Kas Jato Bako. On arrival Peter gave us a nice tour of the island. When we arrived at the house there was already a welcome drink waiting for us. The beautiful surroundings and the house itself, so complete, we felt at home immediately. The house is very nice decorated and spacious, and what about the garden...wow. In and outside the garden there is plenty to see, from parrots to goats and donkeys to iguanas. With a car, all the sights and beaches within easy reach. In short: a wonderful week, with beautiful scenery and a beautiful "home" with all modern conveniences. Kas Jato Bako and Bonaire...we'll be back!

from £87 / night

£609 / week

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Bahamas holiday apartment rental

Treasure Cay apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £352 / night

£2,439 / week

1 / 10

Caribbean holiday villa rental

West End villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Unbelievable” If you want a luxury vacation in the BVI, go no further than the limin house. It is gorgeous in every way, spacious and appointed with more comforts than you have in your home. It is no wonderful that you want to stay there,swim in the pool, grill out and enjoy the bay below. so if you are thinking about accommodations in the BVI, look no farther. The owner and manager were just wonderful and making the reservation was easy. If I am ever in the BVI, the limin house will be where I stay.

from £671 / night

£4,690 / week

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Holiday home rental

Grand Turk house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Very Comfortable and well furnished vacation rental!” I spent a few nights here with my husband. It was great value for money. Clean property with new amenities and air conditioned which is always a plus. Very convenient location as it was very close to a supermarket. Also beaches and a few local restaurants were all whithin walking distance. Damian and Xiomara, the owners were very friendly and accomodating to any questions we had. Overall great stay!

from £92 / night

£633 - £962 / week

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Holiday villa with shared pool in Caribbean

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Exceptional!” Loved our time at windhaven! There are so many amazing things about this place, I hope I will not forget any in my review. The villas are extremely well equipped and decorated simply and tastefully. They have state of the art appliances (including a washer, dryer and Weber BBQ), surround sound with multiple docking stations, large storage facilities on the deck for outdoor equipment like kites and boards, great amenities, a cooler for day trips, beautiful and comfortable furniture, emergency kits, kayaks, there is a shared pool and the grounds are kept beautifully. The manager is fantastic and always makes sure that all your needs are met. The location is fantastic! The beach is extremely safe and quiet. The water is calm and even on windier days, very safe for children. Never any undertow. The clarity is unmatched. There is a grocery store located 5 min away by car. It has everything you can imagine. Great vegan selection with amazing produce and beautiful fish and meat options. The prices are reasonable (we spend Christmas in Barbados, so the pricing TCI are much cheaper!)The shopping is right around the corner from the gourmet grocery store. Windhaven is amazing for kiters but is also perfect for non-kiters. It would be an ideal place for an intimate wedding. The grounds are beautiful and the beach, in my opinion, much nicer and appropriate for a wedding than Garce Bay. We have already booked for the next few years!!! It is that amazing.

from £891 / night

£5,581 / week

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Holiday villa rental

Long Bay Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £410 / night

£2,869 / week

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Holiday villa with swimming pool in Caribbean

Virgin Gorda villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £523 / night

£3,658 - £11,255 / week

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Holiday villa with swimming pool in Caribbean

Providenciales villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £282 / night

£1,970 / week

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Holiday villa with shared pool in Bonaire

Bonaire villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

“no hassle scuba” we stayed here with another family in June for our first time on Bonaire. We absolutely loved it! We dove at "the Cliff" right off the back yard multiple times. It was wonderful to be able to dive without even needing to leave the villa! Snorkeling here was excellent too.The set up is perfect for divers. Dive Friends was SO close and convenient. Lamber was such a kind person and so helpful with anything we needed. He was always very prompt with email communication prior to the trip and set up our reservations for a truck and for dive needs. We feel like we happened upon the best place and the best person on Bonaire!

from £315 / night

£2,200 - £4,104 / week

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Holiday cottage rental

Charlestown cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“A beautiful location and climate with wonderful views of the sea” We stayed in one of the Innisfree cottages in February 2013. The cottage and its amenities fully lived up to the owner's description. Innisfree is located about half way up the mountain in a rural location at the end of a track, which like many of the roads on Nevis could have been better maintained. All the facilities in the cottage, although basic, worked well, including the wi-fi, and everything was very clean, tidy and pleasantly decorated. The cottage is situated in a lovely garden and Veronica and Brett kindly invited us to help ourselves to their homegrown salad, which we did! The views over the sea and surrounding countryside are truly spectacular and the gentle breeze at that altitude meant that the temperature was never oppressively hot. We hired a jeep from Mervin Powell who has his garage based at the end of the track - a 4WD is essential given the location of the cottage, a few miles outside Charleston. There are also some very good local walks from the cottage. Veronica advised us on the hire car and made numerous arrangements for our local transport and provided lots of local knowledge in a very efficient and friendly way. Veronica and Brett were excellent hosts and we very much enjoyed meeting them, and their son Nelson, and two dogs Daisey and Goldie, who greeted us like long lost friends each day!

from £94 / night

£610 / week

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Holiday home in Caribbean

Fitts house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

“Turtle Beach” Parsplace is in an ideal location. It's just north of Bridgetown, on the west side of the island, lending itself to nice, calm waters - ideal for snorkeling and diving. When I was there, baby Loggerhead turtles were hatching almost every day on the beach right in front of our building. There had to be a few hundred of them. The scenes were just as you see on television. What a treat!

from £207 / night

£1,126 / week

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Trelawny Parish holiday home rental

Falmouth house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Secound Time the Charm!” My sister and I loved it the first time we went we couldn't think of another place to be. It was a very comfortable and relaxing time. Away from the cold of the us. The neighbors was nice and Delmar was as charming as ever.

from £94 / night

£610 / week

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Holiday cottage in Caribbean

Long Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Shangri La” This is a beautiful spot. The cottage itself was very clean and lovely. The sheets were excellent, and the kitchen had every cooking utensil needed, along with heavy bottomed cookware (excellent for cooking that cracked corn for grits!) Sara and Dan are very knowledgeable, and generous with said knowledge. The beach is a short walk and is gorgeous, and quiet. No complaints whatsoever!

from £141 / night

£868 / week

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Holiday home in Caribbean

Falmouth house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Cute, clean and quiet = a wonderful place to rent” We rented a home instead of the all-inclusive deal for a purpose - to meet the people of Jamaica and experience their culture. Monique was wonderful to talk to and deal with. She always replied quickly to any questions we had. Her home is very cute, clean and quiet and that's just what we wanted. A nice and safe community too. Her home is close to a beach, restaurant and the town of Falmouth. Many other must-see sights are close by. We would certainly rent from her again.

from £122 / night

£844 / week

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Holiday villa with swimming pool in Caribbean

West End villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £657 / night

£4,596 / week

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Holiday villa in Caribbean

Sunset Crest villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £492 / night

£3,441 / week

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Caribbean holiday apartment rental

Silver Sands apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“I love the villas” I have been to Barbados quite a few times and saw a no.of nice places on the island, but wish to say that Barbados without Inchcape would not be the same. The Inchcape Seaside Villas are so different from all the other accommodations and they are at such a high quality level. We followed the advice given in Inchcape's in house brochure this time and had dinner at such high end restaurant as The Cliff and also at the local rum shop Chicken Reta's close to the villas and both were excellent in their own category. To have the Oistins fish market close by and the best supermarket on the island, Big B, just a few minutes drive away is very convenient. The owners also sent us to "Surfer's Bay, "Café Luna" and "Tapas" and all delivered up to our expectations. The beach at the villas is a dream come true, the sand is white, the water clear, turquoise and all shades of blue. I love all about the Inchcape Seaside Villas and will surely be back as soon as possible.

from £422 / night

£2,955 / week

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