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Featured Villas in Leeward Settlement

Grace Bay Beach Ocean Villas

3.5 star property
9.0 out of 10, Wonderful, (144)
"Beautiful apartment very spacious and clean. Luz was very friendly and amazing. We highly recommended the Grace Bay Villa."
The price is AU$695
includes taxes & fees
5 Dec - 6 Dec
Grace Bay Beach Ocean Villas

Grace Bay Beach Ocean Villas, Bougainvillea Villa. Rated #1 On Trip Advisor.

9.6 out of 10, Exceptional, (58)
"This is a pretty place. Easy to get away. The room was very nice and the common area around the small pool was pretty (get your mosquito spray out). Luckily, I found the place on my own. 2 taxi drivers were lost trying to get there. As well, I stumbled onto and into the room; I finally was able to call someone and 45 minutes later, a nice lady, Luz, showed up to say hi. Good that I was in the correct room. But, it is away - it isn’t close to the downtown bustle of Grace Bay and the...
The price is AU$593
includes taxes & fees
4 Dec - 5 Dec
Grace Bay Beach Ocean Villas, Bougainvillea Villa. Rated #1 On Trip Advisor.

WOW! Waterfront Chalk Sound Oasis w/ Infinity Pool. Kayaks & Canoe

9.6 out of 10, Exceptional, (34)
"The house was well equipped and comfortable with plenty of gathering space for our family. The deck, pool area and dock were all nice spaces with spectactular views. We enjoyed watching the sunrise and sipping coffee overlooking the sound. We had a maintenance issue with the pool, but property manager and maintence man addressed it immediately. We truly enjoyed our stay and are thankful to have made wonderful memories on Chalk Sound."
WOW! Waterfront Chalk Sound Oasis w/ Infinity Pool. Kayaks & Canoe

Palm Jewel - Luxury villa, private outdoor oasis w/pool, walk to SAPODILLA BEACH

10.0 out of 10, Exceptional, (83)
"2 Families shared this home for a week. Absolutely beautiful home, great location to the beach, plenty of space for everyone to spread out in the house. Communication with the Owner and Property Managers was quick and always helpful. We all enjoyed having the refreshing pool to jump in whenever we wanted. Highly recommend this home and location. "
Palm Jewel - Luxury villa, private outdoor oasis w/pool, walk to SAPODILLA BEACH

Grace Bay Beach Ocean Villas, Oleander Villa. Rated #1 On Trip Advisor.

9.8 out of 10, Exceptional, (44)
"Up until the day we checked out it was wonderful. The pool was clean and just the right temperature. The beach was very close and private. Beach towels are provided so don't bring those and save space in your luggage! It was more relaxing than being at a larger resort with many people. Hurricane Oscar flooded our unit the morning we were supposed to leave, but the owner and his staff were amazing. At that moment I knew I made a great choice in reserving here. "
Grace Bay Beach Ocean Villas, Oleander Villa. Rated #1 On Trip Advisor.

Island Escape- Long Bay Beach , private pool

10.0 out of 10, Exceptional, (36)
"Awesome"
Island Escape- Long Bay Beach , private pool

Caribbean Sea Breeze Villas

3.0 star property
9.2 out of 10, Wonderful, (82)
"The place is beautiful it’s clean and has everything you need and having the beach in your backyard is so relaxing sitting out while the sun rises "
Caribbean Sea Breeze Villas

Blue Beauty - Villa HIDEAWAY welcomes you to Grace Bay Beach - Private Pool.

9.6 out of 10, Exceptional, (88)
"The house is charming and just a short walk to the beach and the best snorkeling on the island. We had some issues that were beyond the control of the property manager and she was responsive, made sure things were fixed and that we were satisfied. We had a fantastic vacation and Charlene could not have been a better host!"
Blue Beauty - Villa HIDEAWAY welcomes you to Grace Bay Beach - Private Pool.

SunSeaSand - 1Bdrm Seaside Unit A - Long Bay Hills

10.0 out of 10, Exceptional, (13)
"Has everything you need in a very safe location?"
SunSeaSand - 1Bdrm Seaside Unit A - Long Bay Hills

Crystal Sands Villa! BEACHFRONT Sapodilla! UNBELIEVABLE!! Private pool! Palapas!

10.0 out of 10, Exceptional, (146)
"I had an amazing time with my wife and kids. The house was clean, comfortable, and safe. We had a great time! The kids had a great time. We were all sad when it was time to leave. We will definitely come back next year. "
Crystal Sands Villa! BEACHFRONT Sapodilla! UNBELIEVABLE!! Private pool! Palapas!

Bonefish Haven Turks & Caicos Oceanfront Villa with Pool and Dock

9.8 out of 10, Exceptional, (155)
"We had a wonderful stay at Bonefish Haven. It was away from the resort area of the island which was perfect as it was a quiet and private spot with a beautiful view, just the way wanted. Tina (owner) and Shelly (property manager) were both fantastic. They were very communicative and helpful and answered quickly to any questions. We recommend!"
Bonefish Haven Turks & Caicos Oceanfront Villa with Pool and Dock

2 Bedroom Villa With 360 Degree Views Set High On Hill On 5 Acre Estate.

9.8 out of 10, Exceptional, (89)
"Cottage was awesome, had everything we needed for our stay. Our host were the best and communication is on point."
2 Bedroom Villa With 360 Degree Views Set High On Hill On 5 Acre Estate.

Gorgeous Waterfront Villa w/ HUGE Outdoor Patio & Concierge Services!

9.8 out of 10, Exceptional, (38)
"Loved everything about this place. It was close to everything and tuck away from the hustle bustle if you want some great quality family time. A great experience overall - will definitely stay here again next time."
Gorgeous Waterfront Villa w/ HUGE Outdoor Patio & Concierge Services!

Grace Bay Beach Ocean Villas, Hibiscus Villa. Rated #1 On Trip Advisor.

9.8 out of 10, Exceptional, (61)
"We’ve just left TCI this morning and already missed Hibiscus. The villa is very clean and convenient. It has AC in all rooms. The kitchen is well equipped. The vila is short walking distance to the beach. Luz is always there whenever we need anything. We love her! Chris, the owner, is very flexible. He allowed us to check out late as our flight was not leaving TCI until 4pm. Thanks, Chris & Sarah for such a beautiful place, adding memories to our first vacation in TCI. We will be back!"
Grace Bay Beach Ocean Villas, Hibiscus Villa. Rated #1 On Trip Advisor.

Sea La Vie - Beachside 1 Bedroom Unit #6

10.0 out of 10, Exceptional, (53)
"Everything was great! Host was very helpful and attentive. Definitely would recommend. Thanks again see you soon. "
Sea La Vie - Beachside 1 Bedroom Unit #6

Sea La Vie - Beachside 1 Bedroom Unit #5

10.0 out of 10, Exceptional, (66)
"We always enjoy our stay here! Majid is the best host! "
Sea La Vie - Beachside 1 Bedroom Unit #5

C House Villa. Newly built in Long Bay Hills, Providenciales

9.8 out of 10, Exceptional, (10)
"Our stay at C House Villa was almost perfection. From the time I booked and to our check out, both the owner and property manager were immediately available regarding communication. Hadn’t experienced anything like that in prior rentals. My husband and I loathe rentals but this trip required it and we don’t regret it. The pictures captured the true reality of the house. For that we were grateful. The pool was a must and I’ve were so glad that it was the perfect size and clean. There were a...
C House Villa. Newly built in Long Bay Hills, Providenciales

Reef Tides Luxury 4 Bedroom Beach House with Private Pool. Family-Friendly!

10.0 out of 10, Exceptional, (41)
"Very impressed with this house and the owners/management. Excellent layout with multiple living areas. We had 8 family members and the 4 bedrooms with 4 king sized beds with separate bath worked perfect for us. Beautiful view right on the coast, everyday was wonderful just spending time at the house. Highly recommend staying here."
Reef Tides Luxury 4 Bedroom Beach House with Private Pool. Family-Friendly!

Byculla 4 BR Villa - Canal Front

10.0 out of 10, Exceptional, (145)
"Property and pool were absolutely fantastic. The location on the waterway allowed for fun with the provided kayaks and paddle boards as well as a probated boat chart that picked us up at the private dock. Having a rental car was great to get around. You won’t be disappointed with this house. "
Byculla 4 BR Villa - Canal Front

New Villa - Vitamin Sea on The Water - Walk to Sapodilla and Taylor Bay

9.2 out of 10, Wonderful, (11)
"Property was great - very clean and well maintained. Property manager was awesome - very helpful and easy to get in touch with when issues came up. Plus, she helped to get reservations at a few restaurants. Pool and hot tub are amazing! We used the kayaks and paddle boards daily - even our kids were able to use on the Chalk sound as there aren’t any waves and the wind was calm(er). The Sapodilla beach is a short walk (3 min) but the only down side - it was a busy road so with younger kids, you...
New Villa - Vitamin Sea on The Water - Walk to Sapodilla and Taylor Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Leeward Settlement

The Atrium Resort

3.5 star property
8.2 out of 10, Very good, (176)
"The layout of the property was ideal. The amenities were within close proximity and well maintained. The parking facilities were also great. Overall, I would definitely recommend and return if possible. My experience at the front desk was also warm and welcoming. However, my only gripe somewhat is, the stairs leading up to the reception is difficult with heavy bags. I would recommend a ramp that would help reduce the strain on customers, and would also be conscious of persons with different...
The Atrium Resort

Checkers Vacation Homes

3.0 star property
7.0 out of 10, Good, (32)
"Very quiet and clean "
Checkers Vacation Homes

Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2

9.8 out of 10, Exceptional, (147)
"Property was perfect. Ben was amazing and super friendly. Loved the comfortable beds. The view is stunning. The water toys are perfect. "
Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.