Five Cays Settlement Rentals

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113 Houses

The Babbington Villa

Five Cays Settlement villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$913

Great rentals within 20 miles that match your search

Edge of Paradise 3 bedroom Luxury Villa steps to Grace Bay

Grace Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,130

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Price per night from

$698

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

Providenciales house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$3,015

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: Air conditioning Private outdoor pool (unheated)

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Price per night from

$628

Casa de Isle right off Taylor Bay

Providenciales villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$490

“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: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,130

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$291

SunSea houses (Sea house)

Providenciales villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$286

Three Cays Villa

Providenciales villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,027

Gracemir House in Grace Bay, Providenciales, TCI

Grace Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$514

Windchaser Alize Villa

Long Bay Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,312

Samsara TCI, Bespoke Luxury Caribbean Beach Vacation

Turtle Cove villa

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 22

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$5,480

Villas 5 bedroom Main & 4 bedroom Guest house

Providenciales villa

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 18

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,826

Sunrise Ridge

Grace Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 50 minutes

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$912

Affiniti Villa

Chalk Sound National Park villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 56 minutes

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,255

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

Whitby villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,255

Blue Mountain Villa-Turks & Caicos

Providenciales villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$913

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

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$839

Sea Breeze 6 Bedroom Villas - Beachfront

Long Bay Beach villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$4,050

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

Providenciales villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,060

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: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,997

Sea Breeze 2BR Villa - Beachfront

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,369

Ocean Dream 3 BR Villa Blue

Long Bay Beach villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,597

New Modern Beachfront 3bd/3bath with private pool

Long Bay Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$2,162

Ocean Dream 5 BR Aqua

Leeward villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$2,567

Endless Blue Villa -8 Bedroom Waterfront

Turtle Cove house

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 15

Responds fast! avg. 3 hours 37 minutes

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$2,966

OCEAN SEACRET

Turtle Cove villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$856

Grace Too - Classically Caribbean, perfect for lazy days entertaining

Grace Bay villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$2,852

Sugar Apple Villa - A modern, waterside base

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,597

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: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,027

Villa Blu

The Bight Settlement villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 44 minutes

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$742

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

Long Bay Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$586

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

Long Bay Beach villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,599

Sleeps 10 in Grace Bay!

Leeward house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,426

Luxury Stunning Private Beachfront Villa Overlooking Famed Parrot Cay

North Caicos villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$2,852

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

Long Bay Beach villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$970

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

North Caicos villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Air conditioning Private outdoor pool (unheated)

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Price per night from

$1,757

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