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Leeward Rentals with Pools

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249 Houses in Leeward with pools

Nearly beachfront 4 bedroom villa

Leeward villa

4 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$1,680

2 Bedroom Condo in the heart of Grace Bay

Leeward apartment

2 bedrooms / 3 bathrooms / sleeps 4

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Price per night from

$864

Ocean Dream 5 BR Aqua

Leeward villa

5 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$1,890

BRAND NEW Aqueous - Sunset Beach Villas TCI

Leeward villa

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 29 minutes

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Price per night from

$1,728

10% Discount March - May 2022 Seagrace Villa is 5BDRM Waterfront

Leeward villa

5 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$1,504

Villa Alee - Brand new luxury villa - Only 10 min walk to Grace Bay beach!

Leeward villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 29 minutes

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Price per night from

$922

Breezy Villa is a 4 bedroom Villa with Spectacular Water Front Views

Leeward villa

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$1,582

LIQUID LUXURY - NEW NEW NEW TURKS & CAICOS PRIVATE VILLA ON THE WATER

Leeward villa

3 bedrooms / 4 bathrooms / sleeps 7

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Price per night from

$1,440

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Price per night from

$7,560

Great rentals within 20 miles that match your search

BAREFOOT PALMS, Kick Back and Relax Tiki Style!

Providenciales villa

3 bedrooms / 2 bathrooms / sleeps 6

“Fabulous Villa” I recently spent 4 days in this lovely home and highly recommend it. I have stayed at many villas in the Caribbean and none have been as well maintained or had as much attention to detail shown as Barefoot Palms. The landscaping is gorgeous with lots of palms and flowering trees. The back yard is to die for...nice pool, lounge chairs, sitting area and the best part of all - a great Tiki bar. The outdoor space is great for kids and adults, and is very private. Inside, the first thing you notice is how fresh and clean the house smells. Not musty like some villas. The layout is great and the decorating is perfect..casual and beachy, yet upscale. You can tell the owners take a lot of pride in their home. The kitchen is well stocked, there are TVs and DVD players in every room, there is an alarm system in the house, and beach chairs, coolers and umbrellas are provided. The villa is located in a quiet, gated neighborhood and is a short walk to a great beach or a short drive to the main section of Grace Bay Beach. The owners are great to work with - very responsive and can answer any and all questions about the island. I can't wait to go back!

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Price per night from

$634

BEACH FRONT PROPERTY! 6 Bedroom on Grace Bay Beach ,Sleeps 14

Grace Bay villa

5 bedrooms / 7 bathrooms / sleeps 14

“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!

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$4,377

Casa de Isle right off Taylor Bay

Providenciales villa

3 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$445

Villa Tropica - Near beach, Luxury Villa, Pool

Providenciales villa

5 bedrooms / 5 bathrooms / sleeps 12

“My new favorite island!!! Not to mention a terrific home...” This was our first time visiting Turks & Caicos and I have to say that it was an extremely impressive experience. We were a group of 5 adults and 4 kids ranging from 15 months to 7 years old and this home suited us perfectly. I can tell that the pictures of the home do not due it justice as it is even more beatiful in person. In a word: Immaculate. First of all the home was amazingly clean. I mean spotless. The furnishings are all in great taste and of superior quality. Nothing about this home feels cheap or out of place. The Beds were very comfortable, the linens were excellent, beach towels were there, clean and ready to use the second we arrived. After traveling with young children it was relief not to have to worry about the house. The gated community and gated property felt very secure and safe. The pool and property outside was just as impressive as the inside. My entire group cannot wait to get back there. The home has a resort like feel with all the privacy you could ever want. The negatives are so minor they are hardly worth mentioning: there are mosquitos on a tropical island in July, no suprises there. Some in my party were more susceptible than others, but by and large if you use spray you will be fine. There are quite a few dogs in the area (all nice and most with collars) but they can be heard barking at night sometimes. We loved the neighborhood and the proximity to the beach (i timed it: 38 seconds drive, and thats with the circle and the speed bump).. We always felt close to everything. We explored the entire island and loved every part of it. The restaurants are superb, the kids loved the Conch Farm and every beach was nicer than the last, truly some of the nicest white sand beaches I have ever seen and they were NEVER crowded. We all universally loved Villa Tropica and cannot wait to stay there again..

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Price per night from

$1,037

BEST OF ROYAL WEST .... OCEAN FRONT Premium Suite on Grace Bay

Grace Bay hotel apartment

1 bedroom / 1 bathroom / sleeps 4

“Paradise Found” Just returned from 6 nights at the Calabash Suite and would like to add my enthusiastic and positive comments to those of previous renters. The suite is wonderful, as nice and reasonably priced an accommodation as I think you could find on Provo. The furnishings are comfortable and tasteful, the kitchen well-equipped, the sheets and towels all of high quality and in great condition. The fact that the cleaning crew came in and performed a mid-stay cleaning helped to maintain its neat and clean condition so it always seemed fresh. The media center set-up includes a large flat screen to use in the event you wish to watch TV or a video. There's even an extra phone for free calls to the states. Andrew has gone to great lengths to make his guests feel comfortable and his gestures of providing detailed written information/instructions as well as a card and other amenities are welcome touches. We loved the location, virtually across the street from Coco Bistro and a short drive from other restaurants, the Bakery, food store and other shopping. As the resort is located near the eastern end of the beach, there isn't ever a lot of beach traffic so you never feel as though you're competing for space with others or part of a bustling resort. The resort's pool, bar and restaurant, beach facilities, towels and chairs are all available for use so you get to enjoy those resort amenities as well. As others have pointed out, the best feature of the Suite might be the veranda, which directly overlooks the beach and affords spectacular sunset photo ops. I must have taken the same photos every day our entire stay - they were just too beautiful to pass up. Andrew was a pleasure to work with, well-organized in his rental process and quick to follow-up whenever I had questions. I will - or have - made arrangements to return. Thanks, Andrew, for sharing this little part of Paradise.

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Price per night from

$749

THE GECKO HOUSE with awesome pool! Grace Bay

Grace Bay house

1 bedroom / 1 bathroom / sleeps 4

“Just perfect!” This little (most suitable for couples, or solo traveller) house is quite charming and is perfectly located for either an "all-action" island holiday, or a totally inactive "retreat". It's well screened, so I never had any problems with mosquitos. The island has many wonderful restaurants nearby, but the house is also provided with a gas barbecue so one can easily self-cater as and when. A hire car (do pre-book) is essential, but two bicycles are also provided which are a fun a way to explore and/or get some exercise. The house is well equipped with plates, glasses, kitchen basics - and of course wifi. The house is down a quiet lane with a couple of properties on either side, but not too close. I felt totally safe in this location - and on the island generally. It's a very friendly place. The beach and shops/restaurants are only a short walk/drive away. Them famous Coco Bistro is 3 mins away! A super local agent is always on hand to provide assistance and answer any questions, but I never had any problems. The owners, Nathaly and Jacques, were also in contact to make sure that I was happy and to suggest places to visit (weekly fish-fry event is a must). Overall a totally hassle free and most enjoyable holiday experience - just perfect and I would highly recommend "That Lovely Gekco House" (by the way I only saw a few little ones on the deck, and they were tiny not Jurassic!).

Responds fast! avg. 14 minutes

Match: Swimming pool

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Price per night from

$231

Leisure in Paradise

Providenciales apartment

1 bedroom / 1 bathroom / sleeps 3

“Brilliantly friendly place in an excellent location” We spent 2 weeks in La Casita, 2 adults and 2 children under 5, rented the ground floor apartment, which is at the front of the property, facing east. The room was spacious enough for the spare bed and the baby cot and there was plenty of storage for our clothes, toiletries and other things. The room was equipped with tv, Wi-Fi, fridge, high powered microwave, kettle and cutlery/plates. All beds had netting over them and the room had aC as well as a ceiling fan. The bathroom had a great shower and two basins, which was very handy with two kids around. The hot water seem to never run out, which is handy when the whole family has 2 showers a day. There was a brand new soap in the bathroom as well as kitchen towels and insect repellent. The veranda was enclosed, perfect for late night drinks without the night bugs, and sunny breakfasts in the morning. We had 2 beach chairs, a beach umbrella and kids' beach toys at our disposal. There was a bbq, mini electric stove and pots for us to use. The pool was well kept and very pleasant. The best beach on Earth was literally 5 minute walk away from the house, so if you want to pop back to the house for something you don't need a 30 minute round trip. La Casita is located in the safe Leeward area of the island, a quiet and guarded residential area, a far difference from the hustle and bustle of the busy resorts, yet close enough to town if you wanted to eat out. If you walk about 10 minutes on the beach you end up at a resort beach (which are still public), you can walk into their restaurant for a lovely meal. The hosts were very accommodating, approachable and friendly. At the time of booking they were more than happy to answer any of my questions, and I had a lot of them, and they did not disappoint. I have already recommended La Casita to a friend, who booked a week in September. I would not hesitate to recommend this friendly, quiet and lovely place to anybody.

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Price per night from

$230

SunSea houses (Sea house)

Providenciales villa

2 bedrooms / 1 bathroom / sleeps 4

“Turk and Caicos Island” The property is wonderful, it is away from the beaten path, but yet with in 5 mintnutes of most things. The kitchen is very well equipped and any issue a addressed immediately. To clarify, we broke a shower head, within an hour it was repaired. No muss non fuss. The owners and the property management team were great to deal with.

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Price per night from

$288

Romantic cottage 3 mins from stunning Grace Bay beach.

Providenciales cottage

3 bedrooms / 2 bathrooms / sleeps 5

“"Total Bliss"” My husband and I had a wonderful, relaxing vacation spent at "Columbus Cottage" The whole experience; the Island, the house/pool, amazing beach, the restaurants and the people really exceeded our expectations! We immediately felt so comfortable and relaxed in your peaceful Island paradise. The location was perfact - even without a car, the taxi works ok- we now know what to expect for next time! It's Island Time... Spent the mornings at the beach, short walk nice way to start the day. The beach is amazing and private... afternoons poolside :), and went into town for dinner usually timing with a sunset view over the water. Many wonderful restaurants to choose from! We didnt feel the need to do any tours, golf or explore as expected since we were perfactly content with the total bliss right there within easy reach! Denise was very warm and welcoming, genuinely concerned for our well being - she thoughtfully had a bouquet of flowers and an anniversary card awaiting us when we arrived! - and was nice enough to make arrangements with a taxi driver for our needs throughout the week. We loved the beautiful furnishings in the 'cottage' - But have to say, the private pool was our favorite perk! The setting is very private even though there are neighbors on both sides -can't see homes from property. Thank you also for providing the Wifi - It was helpful to be able to check in. The home also provided plenty of security if that is a concern - although it's in a quiet neighborhood - we felt fine.. This was our 1st "home" rental so we were initially a bit cautious but Jane was very personable, responsive and provided us with plenty of info in advance to satisfy our concerns...seem like lovely people. Looking forward to a return visit!

Responds fast! avg. 3 hours 6 minutes

Match: Swimming pool

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Price per night from

$409

Windhaven 2 Bedroom Villas on Long Bay Beach

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.

Match: Swimming pool

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Price per night from

$1,094

Villa Wyakha - 1 BR On Beach - Ocean view - Pool - Tiki Huts (Unit # 2)

Long Bay Beach villa

1 bedroom / 1 bathroom / sleeps 3

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Price per night from

$504

NEW Esencia PLUS- 2BR Ocean View -On Beach - Prvt Pool + Tiki Hut & Car Included

Long Bay Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

“Villa Wayaka” My husband and I rented upstairs unit w/ sumptuous views--foreground of gardens, turquoise water beyond. We felt immediately at home w/ lovely accommodations and nice breezes. Small details were charming surprises, even the wonderfully fragrant aravatik soap. The compound grounds are so peaceful and charming, w/ buddhas next to the salt water pool, a short walk on a path through the jungle to the beach (where we windsurfed/kited, recovering on the sugary, white sand). Ritama thought of everything both outside and inside. During our stay we rented the downstairs, connecting unit for our adult daughter and her boyfriend. This was the way to go. They enjoyed privacy and the garden apt, as well as together time upstairs watching sunrises and sunsets. The staff were helpful in just the right way, leaving us to ourselves, but if we needed their input, they were there for us. Long Beach Bay--it is a miraculous place, not only to engage in water sports, but also to just veg out. The 3 mi. stretch has very few houses, and so few people--we only saw about 15 kiteboarders, a few horseback riders, and the occasional couple stroll by. No place like it---I should know, I've traveled the world widely...Long Beach Bay is special and Wayaka was just a perfect way to experience it. Definitely go there soon before it gets spoiled. It is a rare opportunity!

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Price per night from

$884

BEACHFRONT 1 BR 1 Bath, (Sleeps 4) TOP FLOOR ,high ceilings, gorgeous views

Providenciales apartment

1 bedroom / 1 bathroom / sleeps 4

“An amazing Trip!!” We stayed at the Captain's Suite for 9 days in January. The unit itself is clean, well maintained and extremely comfortable. The view is unbeatable from the balcony. The location was ideal as we were able to simply walk up the beach to multiple restaurants and open air bars. Upon check-in we were treated to a chilled bottle of champagne and a full bag of coffee. Hazlin was wonderful and very helpful during our stay. The only issue we had was that the internet never cooperated for us. We followed the instructions on restarting the system several times but never had any luck. We finally visited the main reception for the resort. The staff was kind enough to share the resort building wifi code with us.

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Price per night from

$570

Esencia Cottage - Private Pool - On the Beach - Intimate, Natural & Serene

Long Bay Beach villa

1 bedroom / 1 bathroom / sleeps 3

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Price per night from

$974

ProvoVilla Condo Grace Bay Turks & Caicos 2BD 2BA

Providenciales apartment

2 bedrooms / 2 bathrooms / sleeps 6

“So relaxing!” We loved it! Place was clean and cozy. Outside shower was awesome. Photoed birds and lizards! Beach chairs were great, loveTommy Bahama! Would rent again

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Price per night from

$362

Gracemir House in Grace Bay, Providenciales, TCI

Grace Bay villa

2 bedrooms / 3 bathrooms / sleeps 8

“A wonderful relaxing experience!” My stay here was wonderful. The house is located in a picturesque and quiet setting. I enjoyed walking to the beach each morning; stopping at the bakery for coffee on the way back. Afternoons were spent doing a little swimming in the blue ocean and lounging on the beach. Shops were close by and evenings were spent dining at gourmet restaurants that are within walking distance.

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Price per night from

$461

Breezy Palms Oceanfront Villa View & Infinity Pool

Providenciales villa

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 18 minutes

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Price per night from

$576

Samsara TCI, Bespoke Luxury Caribbean Beach Vacation

Turtle Cove villa

10 bedrooms / 8 bathrooms / sleeps 22

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Price per night from

$5,029

Amazing Ocean Views - Breezy Contemporary Studio

Turtle Cove condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$230

Westview, 4 bedroom villa spectacular sunset & water views.

Long Bay Beach villa

5 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$807

Westview Gardens 3 bedroom cottage with pool and stunning sunset views

Long Bay Beach cottage

3 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$461

Spacious 1 Bedroom with Picturesque View, Includes Car

Turtle Cove condo

1 bedroom / 2 bathrooms / sleeps 4

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Price per night from

$224

Villas 5 bedroom Main & 4 bedroom Guest house

Providenciales villa

9 bedrooms / 7 bathrooms / sleeps 18

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Price per night from

$1,613

Beautiful villa Grace Bay ( 5 minutes drive from the popular Grace Bay Beach)

Grace Bay townhouse

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 12 minutes

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Price per night from

$254

Sunrise Ridge

Grace Bay house

3 bedrooms / 4 bathrooms / sleeps 7

Responds fast! avg. 3 hours 23 minutes

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Price per night from

$921

Karana 3 BR Luxury Villa - On Beach, Prvt Pool, Serene & Natural - includes SUV

Long Bay Beach villa

3 bedrooms / 3 bathrooms / sleeps 7

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Price per night from

$1,120

New Studio with 360 degree views

Turtle Cove villa

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 23 minutes

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Price per night from

$345

La Vista Azul Pool side Studio Ocean Views

Turtle Cove condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 36 minutes

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Price per night from

$248

La Vista Azul Grace Bay Ocean View One bedroom suite

Turtle Cove condo

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 36 minutes

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Price per night from

$317

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