Leeward Rentals

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137 Houses

Match: Private pool

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Price per night from

$292

Match: Private pool

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Price per night from

$8,245

Ocean Dream 5 BR Aqua

Leeward villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$2,573

Seagrace Villa is 5BDRM Waterfront

Leeward villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$1,804

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Price per night from

$2,716

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

$1,643

Luxury Villa Silvia López

Leeward villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$2,480

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

Leeward villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 1 hour 6 minutes

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Price per night from

$1,281

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Price per night from

$19,400

TC Villas -Villa Allegria -Emerald Point's Gem

Leeward house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 13

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Price per night from

$2,327

Sugar Apple Villa - A modern, waterside base

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,601

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Price per night from

$22,310

Sleeps 10 in Grace Bay!

Leeward house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$1,430

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Price per night from

$1,018

Villa Viatu - Impressive modern luxury – steps away from Pelican Beach

Leeward villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$3,431

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Price per night from

$2,516

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Price per night from

$7,275

Sunsara Villa

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$3,202

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Price per night from

$14,550

Great rentals within 20 miles that match your search

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Price per night from

$700

Villa Oasis - an incredible hexagon shaped villa on the beach in Grace Bay

Providenciales house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Private pool

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Price per night from

$3,023

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!

Match: Private pool

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Price per night from

$629

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!

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Price per night from

$5,032

Casa de Isle right off Taylor Bay

Providenciales villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$491

“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.

Match: Private pool

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Price per night from

$1,133

SunSea houses (Sea house)

Providenciales villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$286

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. 2 hours 52 minutes

Match: Private pool

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Price per night from

$406

The Breeze House , 3bedroom canal front with pool

Providenciales villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Stimulating and relaxing; it washed all the stresses away” The house is modern with clean lines, built on top of a hill. The views from the infinity pool and deck look over the wild salina with the sea in the background whose everchanging colours we tried unsuccessfully to photograph. No-one overlooks the property, and yet it is within 5-10mins drive of the famous Grace Bay beach and all the restaurants and bars. There is an even shorter 2min drive to another long empty beach. The agent was extremely good giving us all the information and help we needed to make our stay a delight. We took the ferry to another island and explored. We had a snorkelling trip. We thought about fishing or horse riding or cycle riding or playing golf but were quite happy just exploring the local culture and relaxing in the wonderful clear blue water of the sea or our pool.

Match: Private pool

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Price per night from

$457

Perfect Next 2 Heaven 2BR Beach Villa w/ Private Pool and Jacuzzi - Esencia Plus

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

$948

Three Cays Villa

Providenciales villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$1,030

Gracemir House in Grace Bay, Providenciales, TCI

Grace Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$515

Windchaser Alize Villa

Long Bay Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$1,315

Breezy Palms Oceanfront Villa View & Infinity Pool

Providenciales villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$915

Samsara TCI, Bespoke Luxury Caribbean Beach Vacation

Turtle Cove villa

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 22

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Price per night from

$5,493

Sunrise Ridge

Grace Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 47 minutes

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Price per night from

$914

Affiniti Villa

Chalk Sound National Park villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,258

Luxury 4BR Caribbean Beach Front Villa w/ Pool and SUV - Karana 4BR

Long Bay Beach villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$1,603

Sea Breeze 6 Bedroom Villas - Beachfront

Long Bay Beach villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private pool

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Price per night from

$4,060

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