Five Cays Settlement Rentals

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74 Houses

The Babbington Villa

Five Cays Settlement villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Sea view Water sports

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Price per night from

$916

Great rentals within 20 miles that match your search

Serene Caribbean Deluxe Beach Front Studio w/ Pool - Karana Studio 2 (K2)

Long Bay Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

Match: Sea view Water sports

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Price per night from

$271

Edge of Paradise 3 bedroom Luxury Villa steps to Grace Bay

Grace Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view Water sports

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Price per night from

$1,136

150 Steps to Grace Bay Beach! Efficiency

Grace Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

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

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

Providenciales house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Sea view Water sports

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Price per night from

$3,035

Windhaven 2 Bedroom Villas on Long Bay Beach

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Exceptional!” Loved our time at windhaven! There are so many amazing things about this place, I hope I will not forget any in my review. The villas are extremely well equipped and decorated simply and tastefully. They have state of the art appliances (including a washer, dryer and Weber BBQ), surround sound with multiple docking stations, large storage facilities on the deck for outdoor equipment like kites and boards, great amenities, a cooler for day trips, beautiful and comfortable furniture, emergency kits, kayaks, there is a shared pool and the grounds are kept beautifully. The manager is fantastic and always makes sure that all your needs are met. The location is fantastic! The beach is extremely safe and quiet. The water is calm and even on windier days, very safe for children. Never any undertow. The clarity is unmatched. There is a grocery store located 5 min away by car. It has everything you can imagine. Great vegan selection with amazing produce and beautiful fish and meat options. The prices are reasonable (we spend Christmas in Barbados, so the pricing TCI are much cheaper!)The shopping is right around the corner from the gourmet grocery store. Windhaven is amazing for kiters but is also perfect for non-kiters. It would be an ideal place for an intimate wedding. The grounds are beautiful and the beach, in my opinion, much nicer and appropriate for a wedding than Garce Bay. We have already booked for the next few years!!! It is that amazing.

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Price per night from

$1,091

Heavenly 1BR Ocean View w/ Private Hot Tub Pool SUV - Wyakha 2

Long Bay Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$595

Windchaser Alize Villa

Long Bay Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,320

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 Water sports

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Price per night from

$6,826

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

$1,066

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

Tropical Paradise Beach Front Penthouse with Pool and SUV - Penthouse (K4)

Long Bay Beach penthouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Sea view Water sports

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Price per night from

$634

Amazing Secluded 1BR Garden Vw BeachFront w/ Outdoor Pool and Jacuzzi - Wyakha 1

Long Bay Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$368

Stunning 1BR Ocean View and Jacuzzi SUV Kite Boarding - Wyakha 4

Long Bay Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$595

Bright 2BR Ocean View Villa w/ Private Hot Tub and SUV - Duplex 1 and 2

Long Bay Beach townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$962

Paradise Breeze-Majestic Ocean Views-Central Location

Turtle Cove condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 41 minutes

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Price per night from

$293

Ocean Dream 2 BR Villa Blue

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Sea view Water sports

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Price per night from

$1,033

Ocean Dream - Studio Blue

Long Bay Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

Match: Sea view Water sports

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Price per night from

$517

Ocean Dream 5 BR Aqua

Leeward villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Sea view Water sports

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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

Match: Sea view Water sports

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Price per night from

$1,607

24 Dolphin Lane

Long Bay Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Sea view Water sports

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Price per night from

$1,320

The Outpost Villa

Turtle Cove villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Sea view Water sports

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Price per night from

$1,090

Indigo Blu - Festive Availability Only

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Sea view Water sports

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Price per night from

$2,868

Clevelander - Beachfront Villa

Long Bay Beach villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Sea view Water sports

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Price per night from

$7,457

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Price per night from

$620

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Price per night from

$354

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Price per night from

$798

Grace Too - Classically Caribbean, perfect for lazy days entertaining

Grace Bay villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Sea view Water sports

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Price per night from

$2,868

3BR Hidden Gem Villa at Long Bay Beach w/ Pool and SUV - Karana 3BR

Long Bay Beach villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Sea view Water sports

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Price per night from

$1,255

New apartment with sea view (unit 2)

Wheeland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Sea view Water sports

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Price per night from

$144

New apartment with sea view (unit 3)

Wheeland house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Sea view Water sports

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Price per night from

$287

Amazing Modern Beach Front Studio w/ Pool and Jacuzzi - Karana Studio One

Long Bay Beach studio

  • Studio
  • 1 bathroom
  • sleeps 3

Match: Sea view Water sports

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Price per night from

$354

Seas the Day TCI and Chill - 3bedroom, 3 bath 2nd floor Condo - 100% renovated

Wheeland apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Sea view Water sports

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Price per night from

$402

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rentals in Five Cays Settlement

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