Five Cays Settlement Rentals

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40 Houses

The Babbington Villa

Five Cays Settlement villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Sea view Private pool

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Price per night from

$916

Great rentals within 20 miles that match your search

Beachside Villa with Pool, Resort Amenities, 500 ft from Long Bay Beach - v1

Long Bay Beach villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view Private pool

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Price per night from

$1,025

Edge of Paradise 3 bedroom Luxury Villa steps to Grace Bay

Grace Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view Private pool

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Price per night from

$1,134

Samsara TCI, Bespoke Luxury Caribbean Beach Vacation

Turtle Cove villa

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 22

Match: Sea view Private pool

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Price per night from

$5,500

Villas 5 bedroom Main & 4 bedroom Guest house

Providenciales villa

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 18

Match: Sea view Private pool

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Price per night from

$1,832

Sunrise Ridge

Grace Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 50 minutes

Match: Sea view Private pool

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Price per night from

$915

Affiniti Villa

Chalk Sound National Park villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 3 hours 56 minutes

Match: Sea view Private pool

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Price per night from

$1,260

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

Long Bay Beach villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Sea view Private pool

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Price per night from

$1,605

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

Providenciales house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Sea view Private pool

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Price per night from

$3,029

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!

Match: Sea view Private pool

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Price per night from

$5,038

“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: Sea view Private pool

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Price per night from

$1,134

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: Sea view Private pool

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Price per night from

$950

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

Long Bay Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Sea view Private pool

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Price per night from

$588

Windchaser Alize Villa

Long Bay Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Sea view Private pool

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Price per night from

$1,317

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

Whitby villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Sea view Private pool

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Price per night from

$1,260

Milestone Villa on Grace Bay Beach

Grace Bay villa

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 38 minutes

Match: Sea view Private pool

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Price per night from

$6,813

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

Providenciales villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Sea view Private pool

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Price per night from

$1,064

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: Sea view Private pool

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Price per night from

$2,004

Match: Sea view Private pool

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Price per night from

$2,289

Modern Beachside Villa with Pool - Perfect for Families, 2 min from beach - v5

Long Bay Beach villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Sea view Private pool

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Price per night from

$1,546

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

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Sea view Private pool

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Price per night from

$842

Sea Breeze 6 Bedroom Villas - Beachfront

Long Bay Beach villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Sea view Private pool

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Price per night from

$4,065

Blue Mountain Villa-Turks & Caicos

Providenciales villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view Private pool

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Price per night from

$916

TURTLE TAIL ESTATE

Turtle Cove villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Sea view Private pool

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Price per night from

$11,450

Ocean Dream 5 BR Aqua

Leeward villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Sea view Private pool

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Price per night from

$2,577

Ocean Dream 3 BR Villa Blue

Long Bay Beach villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view Private pool

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Price per night from

$1,603

Clevelander - Beachfront Villa

Long Bay Beach villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Sea view Private pool

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Price per night from

$7,443

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

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Sea view Private pool

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Price per night from

$1,645

Villa DelEvan Flip Flop

Long Bay Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Sea view Private pool

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Price per night from

$796

Grace Too - Classically Caribbean, perfect for lazy days entertaining

Grace Bay villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Sea view Private pool

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Price per night from

$2,863

Sugar Apple Villa - A modern, waterside base

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Sea view Private pool

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Price per night from

$1,603

Villa Azzurra - Grace Bay retreat for the ultimate island escape

Turtle Cove villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Sea view Private pool

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Price per night from

$6,298

Aqualina Villa is a Luxurious 5 BDR Villa with an Amazing Ocean View

The Bight Settlement villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Sea view Private pool

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Price per night from

$2,285

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

Long Bay Beach villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view Private pool

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Price per night from

$974

Villa Blu

The Bight Settlement villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 44 minutes

Match: Sea view Private pool

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Price per night from

$745

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: Sea view Private pool

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Price per night from

$487

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

North Caicos villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Sea view Private pool

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Price per night from

$1,764

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: Sea view Private pool

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Price per night from

$1,283

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rentals in Five Cays Settlement

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