Five Cays Settlement Rentals

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204 Houses

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

$6,826

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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

TURTLE TAIL ESTATE

Turtle Cove villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$11,473

The White House TCI and Kenard Cruises Luxury Yacht, The vacation you Deserve.

The Bight Settlement villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

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$2,496

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Price per night from

$702

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

Samsara TCI, Bespoke Luxury Caribbean Beach Vacation

Turtle Cove villa

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 22

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$5,511

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

Long Bay Beach villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,088

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Price per night from

$798

Affordable 2 Bedroom in Grace Bay/A6

Grace Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$345

Villa Renaissance 501 Pool/Garden View

Grace Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$631

Below Budget Studio in Grace Bay!

Grace Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Clevelander - Beachfront Villa

Long Bay Beach villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$7,457

Beachside 3bdr Villa with Pool,Resort Amenities,500 ft from Long Bay Beach - v4

Long Bay Beach villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$1,549

Hura Sea Azure - Pristine Long Bay residence for island adventures relaxation

Long Bay Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$3,435

Grace Too - Classically Caribbean, perfect for lazy days entertaining

Grace Bay villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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$2,868

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

$6,310

Affordable in Grace Bay!

Leeward studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Affordable Studio in Grace Bay!

Leeward studio

  • Studio
  • 1 bathroom
  • sleeps 2

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$172

150 Steps to Grace Bay Beach!-The Condo

Grace Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$345

Sugar Apple Villa - A modern, waterside base

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,603

Ocean Front Elegance- Located on Grace Bay Beach

Grace Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$796

Villa Blu

The Bight Settlement villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 44 minutes

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Price per night from

$745

Indigo Blu - Festive Availability Only

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$2,868

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150 Steps to Grace Bay Beach!-The Suite

Grace Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$345

150 Steps to Grace Bay Beach! Studio

Grace Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$213

Second Chances 5 Bed Villa in Grace Bay

Grace Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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$2,577

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

$1,136

150 Steps to Grace Bay Beach! The Cottage

Grace Bay cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$230

150 Steps to Grace Bay Beach! Efficiency

Grace Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

BEACHFRONT 1 BR 1 Bath, (Sleeps 4) TOP FLOOR ,high ceilings, gorgeous views

Providenciales apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“The Captain's Suite makes an already wonderful place even better” My Wife and I returned to Provo after 15 years, and we knew that we wanted a beachfront suite. There are plenty to choose from, but we quickly zeroed in on The Captain's Suite. It is very nicely appointed, and the view from the balcony is lovely. There is no checking in process, as you already have your key. After a hectic day of travel, that's hard to beat. There is also a very modern supermarket near by. Lastly, Will is very easy to deal with, and communication was always prompt. We would both enthusiastically recommend The Captain's Suite.

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Price per night from

$636

Three Cays Villa

Providenciales villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,034

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

Long Bay Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$271

Coral House - T&C

Grace Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$9,018

RED CLOVER SPACIOUS CLEAN AND CLOSE TO THE BEACH.

Long Bay Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 51 minutes

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Price per night from

$320

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!

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Price per night from

$632

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

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