Five Cays Settlement Rentals

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54 Houses

The Babbington Villa

Five Cays Settlement villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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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

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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

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Price per night from

$1,134

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

$5,038

Casa de Isle right off Taylor Bay

Providenciales villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$492

“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

$1,134

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Price per night from

$292

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

$487

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

$950

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

Long Bay Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$588

Gracemir House in Grace Bay, Providenciales, TCI

Grace Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$516

Villa Oceana Beachfront w/3-4 bdrms on Provo, T&C

Providenciales villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“We're Hooked!” We were looking for a relaxing and romantic beach getaway for two and Villa Oceana was the perfect choice for us. Sapodilla Bay Beach is an amazing crescent of white powdery soft sand and crystal clear water with only a handful of private residences. The house is beautiful with an open airy floor plan and beautiful views from almost every room. Just a few steps out your back door and you are on the perfect beach. The beds are very comfortable, and the kitchen is well equipped. The landscaping makes the pool and patio area very private. The beach is never crowded and the beachside palapa is the perfect spot to relax. The owners are wonderful to work with and the local property management will meet you at the airport and make sure you have everything you need during your stay. We rented a car and had no problems getting around the island. The IGa grocery store has a great selection, and they even carry our favorite gluten-free pasta. As on most islands, food is more expensive, but we saved a lot by eating most of our meals at the villa. If you don't want to cook, there are many gourmet restaurants on the island to choose from. There is one restaurant within walking distance of the villa. The water at Sapodilla Bay is very shallow for about 100 meters out. While we were there, it was extremely calm, with only gentle, lapping waves at the shore. If you want big waves, head to the other side of the island. It's only a 30 minute drive to Grace Bay, and it's definitely worth checking out the other beautiful beaches on the island. Just be sure to make it back to Sapodilla Bay for sunset. One thing that no one warned us about was the no-see-ums. They seem to come out at dusk, so be sure to use bug spray to avoid bug bites while you are enjoying the fabulous sunsets. If you are looking for a crowded, touristy vacation spot, then this villa is not for you. But if you want to be immersed in your own private paradise, you won't be disappointed.

Responds fast! avg. 3 hours 24 minutes

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Price per night from

$1,489

Windchaser Alize Villa

Long Bay Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,317

Breezy Palms Oceanfront Villa View & Infinity Pool

Providenciales villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$916

Villas 5 bedroom Main & 4 bedroom Guest house

Providenciales villa

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 18

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Price per night from

$1,832

The Sapphire Villa - 3 - Bedroom Luxury Villa , Long Bay Beach , private pool

Long Bay Beach villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$779

Blue Mountain Villa-Turks & Caicos

Providenciales villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$916

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

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$842

Empyrean Villas - Tangerine

Whitby villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$287

Empyrean Villas - Aquamarine

Whitby villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$287

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

Providenciales villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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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

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Price per night from

$2,004

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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

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Price per night from

$1,546

Second Chances 5 Bed Villa in Grace Bay

Grace Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$2,577

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

$6,813

WATERFRONT, Private POOL at HAWKSBILL HOUSE in Safe and Prestigious Leeward

Providenciales house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$659

Ocean Dream 5 BR Aqua

Leeward villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$2,577

TURTLE TAIL ESTATE

Turtle Cove villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$11,450

Villa DelEvan 4E

The Bight Settlement house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$10,300

Villa DelEvan Flip Flop

Long Bay Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$796

Ocean Dream 3 BR Villa Blue

Long Bay Beach villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$1,603

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

$1,283

Clevelander - Beachfront Villa

Long Bay Beach villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$7,443

Modern 3 Bedroom Villa Minutes from the Beach

The Bight Settlement villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$842

Endless Blue Villa -8 Bedroom Waterfront

Turtle Cove house

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 15

Responds fast! avg. 3 hours 37 minutes

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Price per night from

$2,977

Villa Azzurra - Grace Bay retreat for the ultimate island escape

Turtle Cove villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$6,298

Emerald Waters is a luxurious 5 bedroom villa

Turtle Cove villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,172

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