Five Cays Settlement Rentals

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68 Houses

The Babbington Villa

Five Cays Settlement villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden 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: Garden Private pool

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Price per night from

$1,025

Villa Bellissimo: luxurious penthouse with private sky pool/Jacuzzi

Grace Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Garden Private pool

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Price per night from

$1,460

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Price per night from

$700

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

Providenciales house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Garden Private pool

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Price per night from

$3,027

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: Garden Private pool

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Price per night from

$630

Casa de Isle right off Taylor Bay

Providenciales villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Garden Private pool

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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.

Match: Garden Private pool

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Price per night from

$1,134

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: Garden Private pool

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Price per night from

$487

Gracemir House in Grace Bay, Providenciales, TCI

Grace Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden Private pool

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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

Match: Garden Private pool

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Price per night from

$1,489

Sunrise Ridge

Grace Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 50 minutes

Match: Garden 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: Garden Private pool

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Price per night from

$1,260

Stirling House

Grace Bay house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden Private pool

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Price per night from

$3,435

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

Long Bay Beach villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden Private pool

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Price per night from

$779

Turks Haven Villas 3BR, Luxurious Vacation Rentals, 500 feet walk to beach!!!

Long Bay Beach villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden Private pool

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Price per night from

$1,088

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

Whitby villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Garden Private pool

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Price per night from

$1,260

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: Garden Private pool

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Price per night from

$1,031

Empyrean Villas - Tangerine

Whitby villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden Private pool

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Price per night from

$287

Empyrean Villas - Aquamarine

Whitby villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden Private pool

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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

Match: Garden 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: Garden Private pool

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Price per night from

$2,004

Match: Garden 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: Garden Private pool

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Price per night from

$1,546

Aloe Ville

Providenciales house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 51 minutes

Match: Garden Private pool

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Price per night from

$184

Sea Breeze 6 Bedroom Villas - Beachfront

Long Bay Beach villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Garden Private pool

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Price per night from

$4,065

Milestone Villa on Grace Bay Beach

Grace Bay villa

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 38 minutes

Match: Garden Private pool

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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

Match: Garden Private pool

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Price per night from

$659

Ocean Dream 5 BR Aqua

Leeward villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden Private pool

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Price per night from

$2,577

Ocean Dream 5 BR Azur

Long Bay Beach villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden Private pool

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Price per night from

$2,348

TURTLE TAIL ESTATE

Turtle Cove villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden Private pool

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Price per night from

$11,450

Sea Break 4BR Villa - Beachfront

Long Bay Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden Private pool

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Price per night from

$2,691

Sea Breeze 2BR Villa - Beachfront

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden Private pool

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Price per night from

$1,374

Villa DelEvan 4E

The Bight Settlement house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Garden Private pool

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Price per night from

$10,300

Villa DelEvan Flip Flop

Long Bay Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden Private pool

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Price per night from

$796

Match: Garden Private pool

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Price per night from

$1,019

New Modern Beachfront 3bd/3bath with private pool

Long Bay Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden Private pool

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Price per night from

$2,170

Brand New Beachfront 2bd/2.5bth with 3rd fl rooftop terrace and pool

Long Bay Beach house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden Private pool

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Price per night from

$1,483

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rentals in Five Cays Settlement

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