Five Cays Settlement Rentals with Pools

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204 Houses in Five Cays Settlement with pools

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

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

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

$344

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

$229

150 Steps to Grace Bay Beach! Studio

Grace Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$212

150 Steps to Grace Bay Beach! Efficiency

Grace Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Below Budget Studio in Grace Bay!

Grace Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

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Price per night from

$700

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

$344

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

$3,027

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!

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Price per night from

$630

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

THE GECKO HOUSE with awesome pool! Grace Bay

Grace Bay house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Ahhh mazing” We just got back from staying at the most amazing little house you have ever seen, the lonely gecko house was perfect for me and my boyfriend to have a relaxing and uplifting vacation. We felt safe, and more importantly felt like that house was our home away from home. With the amazing colors and bikes we used offten. They home owners are clearly consider our friends with how well they communicated and valued us as guest. You should book the gecko house now! You will not regret the beautiful house and the amazing beaches right near there!

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Price per night from

$286

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Price per night from

$292

SunSea houses (Sea house)

Providenciales villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$287

SunSea houses (Sun house)

Long Bay Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$401

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

$1,088

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

$594

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

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

Providenciales apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“An amazing Trip!!” We stayed at the Captain's Suite for 9 days in January. The unit itself is clean, well maintained and extremely comfortable. The view is unbeatable from the balcony. The location was ideal as we were able to simply walk up the beach to multiple restaurants and open air bars. Upon check-in we were treated to a chilled bottle of champagne and a full bag of coffee. Hazlin was wonderful and very helpful during our stay. The only issue we had was that the internet never cooperated for us. We followed the instructions on restarting the system several times but never had any luck. We finally visited the main reception for the resort. The staff was kind enough to share the resort building wifi code with us.

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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

$1,031

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

ProvoVilla Condo Grace Bay Turks & Caicos 2BD 2BA

Grace Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Amazing!” This condo was amazing!!! Susie was fabulous from booking, check in, making sure we were okay and check out. I still email Susie and will be staying again here very soon. Clemaris met us there and showed us all around. We had a cute little bathroom with a shower. One of the bedrooms had a 1/2 bath which helped when my sister and I were getting ready at the same time. It had an outdoor shower off the back patio - very cool! The condo is behind Grace Bay Club - very short walk to the beach. Ports of Call shopping and Grace Way Gourmet grocery store was a short distant walk as well. It is shaded around the condo, so we kept the windows open for a nice breeze. My sister and I are beach girls, however we did use the pool a couple of times which was very nice. We met neighbors at the pool and met new friends from Canada. The whole islands electricity went out which has never happened unless there was a hurricane. It was out for about a 24 hour period - Susie emailed checking on us and the neighbor that lives there was going to work that morning (he had a generator) asked us if we need some coffee. His sweet wife, Argentina, made us coffee! The beds were comfortable and we enjoyed cooking at home! This place is a must stay!!!

Responds fast! avg. 1 hour 36 minutes

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Price per night from

$430

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

Match: Swimming pool

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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

Samsara TCI, Bespoke Luxury Caribbean Beach Vacation

Turtle Cove villa

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 22

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Price per night from

$5,500

Amazing Ocean Views - Breezy Contemporary Studio

Turtle Cove condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$327

Spacious 1 Bedroom with Picturesque View, Includes Car

Turtle Cove condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$223

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

Sunrise Ridge

Grace Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 47 minutes

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Price per night from

$915

Affiniti Villa

Chalk Sound National Park villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,260

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

Long Bay Beach villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$1,605

New Studio with 360 degree views

Turtle Cove villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 47 minutes

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Price per night from

$343

La Vista Azul Pool side Studio Ocean Views

Turtle Cove condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$247

La Vista Azul Grace Bay Ocean View One bedroom suite

Turtle Cove condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$315

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