
House vacation rentals in Leeward Settlement
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Top-rated house rentals in Leeward Settlement
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Popular amenities for Leeward Settlement house rentals
House rentals with a pool

2 BR Ocean View- Private Pool- Flame Tree Villa #2
We had the perfect week at Eric’s villa in Long Bay. This was our 8th time to the island so we knew exactly where we wanted to be location wise. The house is everything you need. Very large, kitchen fully equipped, 2 full baths, laundry, TV/internet, and your own private pool. There is another identical house next to this one where you would share the driveway but no one was there our week. Eric went above and beyond letting us check in early and leave late, bringing extra pillows, and delivering fresh pastries every morning from his bakery on the island. We were spoiled. He even rescued us when we needed some help disassembling some kite gear - showed up immediately with a full tool box. As with all of Provo, there are many dogs on the island and these neighborhood dogs loved to bark at night but that isn’t unique to this property necessarily. Driveway is gated which added extra comfort. Lastly the 2 sets of double doors that fully open with screens were perfection.

2b/2b BEACH HOUSE STEPS to GRACE BAY! WiFi,AC,Pool
Just returned from eight days at Nina and Dale's beautiful home. From the time of booking throughout our stay, Nina and Dale were very responsive to all communications. The home is lovely, and the photos of the property are very accurate. It was easy to find from the hosts' detailed instructions, and we felt very safe there. The beds and pillows were comfortable; the air conditioning was cold; ample towels and toiletries are provided; and we particularly appreciated their reverse osmosis 5-gallon water cooler! We didn't use the pool, but we did enjoy the outdoor shower & spigot to rinse off before going in the house. The keypad for entry worked flawlessly, and the gate remote was very convenient. Several grocery stores are a few minutes' drive away, and we had everything we needed in the kitchen for cooking/grilling. Bight Reef/Coral Gardens was a few minutes walk, and the home is also very close to Grace Bay and Smith's Reef. Really an all positive experience. Thank you!

2 Bedroom Spectacular Views
This villa was even better than the photos depicted. Absolutely perfect in every way. Chalk Sound is a truly special place as are the nearby beaches (Sapodilla Bay, and a particular favorite was the very unique Taylor Bay Beach). A rental car for this location is a must, and the short trip to Grace Bay is very worth it (both the town and the beach). You can bring the beach chairs Terri provides or easily rent chairs and umbrellas there. Felt like a luxury hideaway, but with easy access to all of the hot spots around the island. Would give 6 stars if we could!

Caribbean Villa with Pool and Beach Access
I cannot say enough great things about the beautiful home and Patricia and Marvin. They were so helpful . Gave us suggestions of popular restaurants, and local activities. We felt very comfortable in the home. It was like a 3 min walk across the street to the beach. Patricia and Marvin have 5 beach chairs on the beach marked Turks Haven Villas. We had a rental car and every thing was just like 15 min or less to get to. Perfect location. We did have a few questions while there and Patricia was always so responsive and helpful. Beautiful seating area on second floor outside of master bedroom. I enjoyed sitting there in the morning watching the sunrise. The pool was perfect. We felt like we were in a five star resort. Fresh flowers on the kitchen counter when we arrived and on the side tables on the patio. We can hardly wait to go again.

1 BR Apt w/pool - Long Bay Hills #2
Do yourself a favor & book this place!! Spotless home with perfect AC units (I'm usually VERY picky with cleanliness), very WFH friendly (desk, chair, very good wifi, etc), and very safe location! I stayed here as a solo female traveler & never felt the need to even lock my door! Perfect place to stay long term, too - comes with everything you need, it's away from all of the resorts/noise (& fratty people). Incredible price, too! I will only come back to TCI if this home is available! I stargazed in the pool every single night. Jim & Maria are incredible hosts who were so helpful in every way. For example, I'm pretty sure Maria took the batteries out of her fire alarm to put into mine, so she suffered all night, but I didn't have to. They also lent me their paddleboard, gave me endless tips/tricks, & were so kind! Really made the island feel special. Thank you SO much for everything!

SunSeaSand 3Bdrm Oceanview Home -Long Bay Hills
This was the perfect place to stay! it was clean and big and everything about staying there was so easy!

Sea More Getaway
I would like to express my sincerely gratitude. This was the first time I stayed at an Airbnb in Turks. It was wonderful foe my family and I. The place was well stocked with amenities and we utilized all the offerings. From the kitchen, to the pool, to the laundry area. Thank you so much!

Hummingbird Villa - Large pool steps from beach
Loved our stay there! One of the best vacation experiences! Super easy and beautiful!
Weekly house rentals

Casa de Isle, Taylor Bay, Chalk Sound area
Debbie and Dan were exceptional hosts! They clearly care about their villa and maintain it very well. The villa was stocked with a full usable kitchen with all the tools one would need to cook in. The beds were comfortable, the house was very clean and can’t beat the location just a short walk to the beach. We enjoyed the quick walk to Taylor Bay and the villa was equipped with lots of extras like pool/beach toys, towels, etc, and even had a washer and dryer! Debbie and Dan are a wealth of knowledge and had lots of useful recommendations. Thank you for a wonderful stay at Casa De Isle, we will return!

Brighter Days Villa
My mom and I booked extremely last minute and were welcomed right away. The instructions were very clear and the house was easy to find. Beds were very comfortable and we had everything we needed. The only downside was that we could not get the stove/ oven to turn on and weren’t able to cook the food we bought.

Waterfront House - Upstairs
Kaian’s place was spectacular! Very large and had so much room— more than pictures show! Central to the best beaches and right in the middle of everything. The host was so gracious and kind and made us feel like family. This place is a steal grab it while you can!

@Villa 360! Private, Gorgeous Views Near airport
OMG...this home is beautiful inside and out..this is perfect place to rent for your next getaway... the host will reply back quickly if you have any questions or concerns... when I come back I'll most definitely check here first to see if available.

Shalom Cottage
I had a great experience staying at this unit over the weekend. The place was clean, well-maintained and exactly as described in the listing. The host was responsive and made check-in/out super easy. It was the perfect spot for a relaxing weekend and I would definitely recommend it to others. I’d be happy to stay here again! ☺️

Sea Chelles Villa TCI
My husband and have been Airbnb'ing in the Carribean countries for 5+ years in different places and this is spot is the best/our favorite among all those we have visited. The pool and surrounding gardens at Chelle's place are lovely and private. The location is in a great part of the island, close to everything but not too busy or noisy. The ACs in the two rooms made the Villa very comfortable quickly and is well set up for your needs. I know sounds odd for vacation, but we really enjoyed the kitchen and grill to cook when we opted to not restaurant and just hang by the pool for the evening. The beach is short walk from the property. Chelle, the host, is very responsive and has great recommendations for restaurants and activities in TCI. We will definitely be back and hope you all enjoy, but don't tell everyone about TCIs best AirBNB!

Secluded Getaway, Hot Tub & Scenic Water Views
Dawnette’s greeted us as we arrived to the house, gave us a tour, and some recommendations on what to do around the area. The house is nice and sets right on the water of chalk sound. There’s a nearby beach that’s great for families and Las Brisas which offers a good dining experience and kayaks onto chalk sound. The area is nice and quiet, but still plenty to do since nothing is too far. We rented a car for the stay. Dawn was an excellent host and the house was very comfortable. When we come back, this will definitely be the place we stay!

3Bed Gated Villa w Pool, Easy Walk to Beach, Shops
Great place with a great host and property manager. The host and manager were very responsive to any messages sent. Beach is close by and the house is in the middle of everything you would need. The house location was surprisingly quiet for being in the middle of Grace Bay. Great place for kids. They loved the upstairs loft and pool. If we ever return, we would rent this place again.
Private house rentals

Flamingo's Nest at Whitby Beach (North Caicos)
Our stay at Flamingo’s Nest was phenomenal. This house is perfect for an island escape. The house is comfortable and well appointed. The beach is a stone’s throw away, less than a 2 minute stroll. It’s a fantastic beach and we had it almost entirely to ourselves— so different from the crowded beaches of Provo. There is a convenient store (KJs) about a 3 minute drive. North Caicos itself is amazing and worth the extra effort to get to. Everywhere we went we were just about the only visitors there. Can’t recommend both the island and the house enough.

June Plum Hideaway Cottage in Grace Bay, TCI
This place was amazing and Matthew was so attentive and helpful during our stay. Great recommendations and was so responsive and on top of everything! Made the stay so seamless. Highly recommend it here.

Chez Moi Villa, Beach & Pool
Our stay at the villa was absolutely fantastic! From the moment we arrived, we were impressed by how clean and beautifully maintained the property was. The villa itself was outstanding, with elegant decor and all the comforts of home. One of the best parts was its prime location—just a short walk to downtown Grace Bay, where we enjoyed great dining, shopping, and the incredible beach. The gated property gave us an added sense of security, allowing us to fully relax and enjoy our time. We couldn’t have asked for a better place to stay and would highly recommend it to anyone looking for the perfect getaway!

Colibri Gardens Villa - Great value in Grace Bay
The house is fully equipped and has everything you might need. Highly recommended, unless you have any walking limitation. The house is near the grace Bay Area, but the road leading to it is unpaved. So if you plan to walk from and to it, just make sure you have no problem taking short walks on unpaved roads. Our group had some kids and a baby, and that was a bit of a hassle. But other than that, the house is spacious, fully equipped, beds comfortable and location is convenient.

ParadiseONE 2 Suites 3 Bedrooms
Definitely recommend! Host was friendly and the space was enough to accommodate our large family! We enjoyed our stay and would absolutely book again. Pros: Host was extremely kind and helpful to us. Insect repellent and other helpful items were provided to help with our stay. Security cameras etc on property gave us a sense of safety. Water fountain with drinkable cold water provided. Area is pretty central and close to a lot of stuff. Cons: Lots of mosquitoes. Cell phone reception was pretty poor in the units. It does have a lot of bush / trees in the area which causes you to have to be super cautious at night when leaving/entering the property.

Central Hideaway/Kg+Qn Bd/4K 55”TV Ntflx/BchNearby
We enjoyed our week stay at Sandy's place. We rented a small SUV and drove all around Provo. The roads out to North West Point is rough but doable if you go slow and have a high clearance vehicle, we packed our own gear, saw sea turtles and lots of tropical fish right off the beach. We took a ferry to explore North and Middle Caicos on a day trip which was great. There are 2 large IGA grocery stores close by to get anything you want to prepare your own food. The beds were very comfortable, AC units are slim systems which are quiet and very effective air management. Having a washer and drying helped us to pack light and not deal with checked luggage.

Sun and Sea Villas (both) - Family friendly Villas
Being in Turks and Caicos its important to be laid back and go with the flow. We had some hiccups along the way with some things…. but when we reached out they were close by and came to fix everything immediately. The pool was great and we enjoyed it a lot. We didn’t utilize the golf carts because they were not working the first half of the trip and after they were fixed we realized it was easier to just drive to the beach access. Over all decent place to stay.

Coastal Vibes Villa Near Sapodilla Beach
The house was exactly as described and super clean when we arrived! Good amenities.
Quick stats about house rentals in Leeward Settlement
Total rentals
90 properties
Nightly prices starting at
ﺩ.ﺇ588 before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
70 properties have a pool
Destinations to explore
- Grace Bay Vacation rentals
- Grand Turk Vacation rentals
- Long Bay Hills Vacation rentals
- North Caicos Vacation rentals
- The Bight Settlement Vacation rentals
- Chalk Sound Vacation rentals
- Turtle Cove Vacation rentals
- Sapodilla Bay Vacation rentals
- Cooper Jack Bay Settlement Vacation rentals
- Venetian Road Settlement Vacation rentals
- Santo Domingo Vacation rentals
- Las Terrenas Vacation rentals
- Family-friendly rentals Leeward Settlement
- Apartment rentals Leeward Settlement
- Rentals with a fire pit Leeward Settlement
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- Beachfront rentals Leeward Settlement
- Rentals with a washer and dryer Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Waterfront rentals Leeward Settlement
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- Luxury rentals Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with pools Leeward Settlement
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