Leeward Rentals

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136 Houses

Match: Private pool

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Price per night from

$293

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

Match: Private pool

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Price per night from

$2,581

Villa Viatu: Luxury 6 BED Villa, Turks and Caicos

Leeward villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

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Price per night from

$2,934

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

Match: Private pool

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Price per night from

$1,645

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

Leeward villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 33 minutes

Match: Private pool

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Price per night from

$1,283

Match: Private pool

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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

Match: Private pool

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Price per night from

$1,534

Sugar Apple Villa - A modern, waterside base

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$1,606

Match: Private pool

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Price per night from

$22,310

Sleeps 10 in Grace Bay!

Leeward house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$1,434

Match: Private pool

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Price per night from

$1,021

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

Leeward villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Private pool

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Price per night from

$3,434

Match: Private pool

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Price per night from

$2,519

Match: Private pool

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Price per night from

$7,275

Sunsara Villa

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$3,205

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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

$702

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

$631

Casa de Isle right off Taylor Bay

Providenciales villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Private pool

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Price per night from

$493

“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

$1,136

SunSea houses (Sea house)

Providenciales villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Private pool

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Price per night from

$287

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!

Match: Private pool

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Price per night from

$951

Enjoy Secluded Cottage w/ Pool Jacuzzi Beach Front - Esencia Cottage

Long Bay Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Private pool

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Price per night from

$589

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

$517

Windchaser Alize Villa

Long Bay Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$1,320

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

$918

Samsara TCI, Bespoke Luxury Caribbean Beach Vacation

Turtle Cove villa

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 22

Match: Private pool

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Price per night from

$5,511

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

$4,073

Milestone Villa on Grace Bay Beach

Grace Bay villa

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 38 minutes

Match: Private pool

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Price per night from

$6,826

New Modern 4-bedroom Villa, Amazing Pool, Privacy, 500 ft. to Long Bay Beach v10

Long Bay Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$1,033

Blue Mountain Villa-Turks & Caicos

Providenciales villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$918

Aloe Ville

Providenciales house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 51 minutes

Match: Private pool

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Price per night from

$184

2BR Private Villa Long Bay Beach w/ Pool and SUV - Esencia Premiere

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$844

Salty Air, Ocean Breezes, Ospreys, Herons, Kayaks & a Pool plus More-MIZO VILLA

Providenciales villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Private pool

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Price per night from

$1,066

Modern Luxury/Beachfront Villa/Snorkel and Kayak Right from Property!

Providenciales villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 32 minutes

Match: Private pool

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Price per night from

$2,008

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rentals in Leeward

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