Five Cays Settlement Rentals

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The Babbington Villa

Five Cays Settlement villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Waterfront Horse riding

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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: Waterfront Horse riding

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Price per night from

$271

150 Steps to Grace Bay Beach! Efficiency

Grace Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

Match: Waterfront Horse riding

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Price per night from

$172

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Price per night from

$702

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

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

Providenciales house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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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

Match: Waterfront Horse riding

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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

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

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

Long Bay Beach penthouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$634

Relaxing Modern 1BR Garden Vw Beach Front w/ Outdoor Pool and Jacuzzi - Wyakah 3

Long Bay Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$368

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

Ocean Dream 5 BR Aqua

Leeward villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$2,582

Indigo Blu - Festive Availability Only

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$2,869

Salt Life Villa - Canalfront

Leeward villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$918

Clevelander - Beachfront Villa

Long Bay Beach villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$7,458

Salt Air Villa

Leeward villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$1,205

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Price per night from

$354

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Price per night from

$798

Villa Serenity-Water View Suite

Turtle Cove house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Waterfront Horse riding

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Price per night from

$230

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: Waterfront Horse riding

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Price per night from

$1,256

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

Long Bay Beach studio

  • Studio
  • 1 bathroom
  • sleeps 3

Match: Waterfront Horse riding

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Price per night from

$354

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

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Waterfront Horse riding

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Price per night from

$844

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

$5,048

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

$951

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

Long Bay Beach villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Waterfront Horse riding

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Price per night from

$1,608

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

$3,442

Peaceful 1BR Private Cottage w/ Hot Tub Beach Front - Chuchubi Cottage

Long Bay Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Waterfront Horse riding

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Price per night from

$439

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

Peaceful 2BR Ocean View Duplex n Private Jacuzzi SUV Kite Boarding - Wyakha 3n4

Long Bay Beach townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Waterfront Horse riding

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Price per night from

$960

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

Long Bay Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Waterfront Horse riding

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Price per night from

$588

Ocean Front Elegance- Located on Grace Bay Beach

Grace Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Waterfront Horse riding

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Price per night from

$796

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: Waterfront Horse riding

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Price per night from

$1,283

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