Five Cays Settlement Rentals

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85 Houses

The Babbington Villa

Five Cays Settlement villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Safe Private pool

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Price per night from

$918

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BISHOP HOUSE

Five Cays Settlement house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 7 minutes

1 of 2 match: Private pool, Safe

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Price per night from

$230

Great rentals within 20 miles that match your search

Breezy Palms Oceanfront Villa View & Infinity Pool

Providenciales villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Safe 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

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Price per night from

$5,511

Villas 5 bedroom Main & 4 bedroom Guest house

Providenciales villa

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 18

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Price per night from

$1,836

Affiniti Villa

Chalk Sound National Park villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 56 minutes

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Price per night from

$1,262

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

Providenciales house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$3,035

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

$632

Casa de Isle right off Taylor Bay

Providenciales villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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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.

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Price per night from

$1,136

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Price per night from

$293

Gracemir House in Grace Bay, Providenciales, TCI

Grace Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$517

Windchaser Alize Villa

Long Bay Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,320

New! Private Oceanfront Paradise in the LAST of the unspoiled Caribbean.

Whitby villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$1,262

Milestone Villa on Grace Bay Beach

Grace Bay villa

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$6,827

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

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Price per night from

$2,008

Sea Breeze 6 Bedroom Villas - Beachfront

Long Bay Beach villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$4,073

Blue Mountain Villa-Turks & Caicos

Providenciales villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$918

TURTLE TAIL ESTATE

Turtle Cove villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$11,473

Ocean Dream 5 BR Aqua

Leeward villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$2,582

Ocean Dream 3 BR Villa Blue

Long Bay Beach villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$1,607

Clevelander - Beachfront Villa

Long Bay Beach villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$7,458

Grace Too - Classically Caribbean, perfect for lazy days entertaining

Grace Bay villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$2,869

Sugar Apple Villa - A modern, waterside base

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Safe Private pool

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Price per night from

$1,607

Villa Azzurra - Grace Bay retreat for the ultimate island escape

Turtle Cove villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Safe Private pool

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Price per night from

$6,310

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.

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Price per night from

$488

Sunsara Villa

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Safe Private pool

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Price per night from

$3,213

Breathtaking Beachfront Villa on Powder White Sand with Crystal Waters, & Pool

North Caicos villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Safe Private pool

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Price per night from

$1,767

Alta Bella Villa and Spa

Turtle Cove villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$2,639

Villa Viatu: Luxury 6 BED Villa, Turks and Caicos

Leeward villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

Match: Safe Private pool

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Price per night from

$2,934

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

Long Bay Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Safe Private pool

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Price per night from

$589

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

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Price per night from

$1,285

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

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Safe Private pool

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Price per night from

$844

Turks Haven Villas 2BR, Luxurious Vacation Rentals, 500 feet walk to beach!!!

Long Bay Beach villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Safe Private pool

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Price per night from

$976

Empyrean Villas - Tangerine

Whitby villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Safe Private pool

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Price per night from

$287

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

$5,048

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: Safe Private pool

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Price per night from

$951

Empyrean Villas - Aquamarine

Whitby villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Safe Private pool

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Price per night from

$287

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