House holiday rentals in Leeward Settlement

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Popular amenities for house rentals in Leeward Settlement

House rentals with a pool

Superhost
Home in Long Bay Hills
5 out of 5 average rating, 3 reviews

1 BR Apt w/pool - Long Bay Hills #1

CatherineRating, 5 stars4 months ago
The condo was exactly as advertised! King bed was so comfortable, big shower with great water pressure. The pool and patio were lovely. The Host was proactive and responsive and had great local recommendations. This is part of a duplex - so you will have neighbors sharing the pool and patio. There are beach towels in the unit and two chairs and two snorkels to share with the other unit. Great stay 10/10 would recommend 🤣
Guest favourite
Home in Long Bay Hills
5 out of 5 average rating, 45 reviews

2 BR Ocean View- Private Pool- Flame Tree Villa #2

CarlosRating, 5 stars2 days ago
Our stay at Eric’s property was absolutely phenomenal! The property is a perfect blend of modern elegance and cozy comfort, with stylish decor, plush beds, and a spotless, well-maintained space that felt like a luxury retreat. The fully equipped kitchen, high-speed Wi-Fi, smart TV, and serene outdoor area with a pool were just a few of the standout amenities that made our stay effortless and enjoyable. Every detail, from the pristine cleanliness to the thoughtful touches like fresh pastries delivered every morning was excellent. The kids were looking forward every morning to checking to see if Eric had dropped off the pastries! The location was ideal, offering easy access to the beaches (Grace Bay beach etc), restaurants, and shops while maintaining a peaceful atmosphere perfect for relaxation. The Eric’s outstanding communication and warm hospitality elevated the entire trip, even accommodating check out preference. We highly recommend this gem to anyone. You wont regret it!
Superhost
Home in Providenciales
4.9 out of 5 average rating, 41 reviews

3 Bed Beach Oasis on Flamingo Lake w/Private Pool

JuanRating, 5 stars1 month ago
The house was beautifully decorated and is very spacious. Communication with the host was great. The neighborhood felt safe and private. Found some hair in the master bathroom so I believe more attention to details during the cleaning should be given. We also ran out of paper towels as we were only given one roll. Might consider providing a few more household items when guests stay more than just a few days. Otherwise it was an overall good experience.
Top guest favourite
Home in Long Bay Hills
5 out of 5 average rating, 30 reviews

Stunning Luxury Villa w/ Pool and Sunset Views

LisaRating, 5 stars4 weeks ago
Patricia and Marvin were amazing hosts! From check in to check out they were amazing and helpful! The villa is beautiful! They didn’t dare an expense and thought of all the creature comforts. The private pool was so nice to have after a day at the beach. We were so lucky that we chose this little piece of paradise!
Top guest favourite
Home in Providenciales
5 out of 5 average rating, 22 reviews

2 Bedroom Spectacular Views

MissyRating, 5 stars3 weeks ago
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!
Superhost
Home in Providenciales
4.87 out of 5 average rating, 39 reviews

Caya Villa 2 - 2 Bedroom - Island Fusion Home

ChristinaRating, 5 stars5 months ago
We stayed in Caya Villa 2 for 1 week. The house is beautiful & exactly as shown in the pictures. It was spacious, comfortable & clean. They even provided a mid-week cleaning which was great. The bathrooms are awesome & the mattresses are comfortable. The location was decent. It is just a short 10 minute ride into the heart of Grace Bay. However, several of the roads are not paved & there are a fair amount of stray dogs. Although the house is so close to Long Bay Beach, there is no access to the beach (unless you drive for 10+ minutes), so we could not walk to the beach. The major disappointment was that we could not use the beautiful outdoor spaces of the house as we expected because the no-see-ums were really bad (we each had bw 60-100 bites) & the pool was not heated. There is a lot of vacant land in the neighborhood with overgrown vegetation which must contribute to the bugs. The pool was simply too cold for my kids (I was okay w/the temps). Overall, we had a nice week.
Superhost
Home in TC
4.88 out of 5 average rating, 126 reviews

Sea More Getaway

Stephanie Rating, 5 stars1 month ago
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!
Top guest favourite
Home in Caicos Islands
4.92 out of 5 average rating, 13 reviews

Two Bedroom Villa, Long Bay, Providenciales - Eden

MattRating, 5 stars2 months ago
nice home, very comfortable and private. beach walk was reasonably close. home was well stocked.

Weekly house rentals

Top guest favourite
Home in Providenciales and West Caicos
5 out of 5 average rating, 62 reviews

Casa de Isle, Taylor Bay, Chalk Sound area

ChelseyRating, 5 stars1 month ago
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!
Superhost
Home in Venetian Road Settlement
4.76 out of 5 average rating, 33 reviews

Brighter Days Villa

TiaRating, 5 stars2 months ago
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.
Guest favourite
Home in Providenciales
4.98 out of 5 average rating, 41 reviews

@Villa 360! Private, Gorgeous Views Near airport

JacquelineRating, 5 stars2 weeks ago
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.
Guest favourite
Home in
4.95 out of 5 average rating, 19 reviews

Shalom Cottage

CandiceRating, 5 stars1 week ago
We had an amazing time in Providenciales and this was largely due to our wonderful accommodations! Naomi's place was definitely more than advertised, and it screams modern but comfortable stay at the same time. Although it is close to the road, once you are inside you forget about everything on the outside. From the cute amenities in each corner of the rooms, to the design of each space within, you won't want to leave the property. And Naomi?! She was an excellent host! Gave us all the info we needed before, facilitated early check in to drop off our bags so we could peruse the town, and communicated with us throughout our stay. If you're reading this, definitely stay at her place, you won't regret it, and you won't regret having Naomi as your host!
Superhost
Home in Providenciales
4.83 out of 5 average rating, 6 reviews

June Plum Hideaway Cottage in Grace Bay, TCI

AustinRating, 5 stars3 months ago
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.
Superhost
Home in Long Bay Hills
4.73 out of 5 average rating, 45 reviews

Sea Chelles Villa TCI

AlyssaRating, 5 stars1 month ago
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!
Guest favourite
Home in Grace Bay
4.95 out of 5 average rating, 19 reviews

3Bed Gated Villa w Pool, Easy Walk to Beach, Shops

AndrewRating, 5 stars1 day ago
Extremely impressed by this property! This home fulfilled all of our needs and more. Located a very short walk to the beach and shops/restaurants/grocery store this home was super comfortable and convenient. The on site pool also was a wonderful place to relax with our family. We had a two year old with us and the home had a supply of beach toys that she enjoyed every day. They even provided enough beach towels for everyone’s use. We are excited to stay here again in the future.
Superhost
Home in Grace Bay
4.88 out of 5 average rating, 17 reviews

5 minutes walk to Grace Bay Beach

CrisRating, 5 stars4 months ago
Jasmine was a wonderful host. She guided us to the property after Google led us astray. After initially booking the property, she reached out to answer any questions we might have which we had many since this was our first visit to the island. She had excellent recommendations about getting a rental car, snorkeling excursions and scuba diving. The property was immaculate and completely as described & photos. All kitchen appliances, flatware, dishes, toaster, coffee maker, pots and pans available. Beds were perfect to sleep on and ample pillows. Ceiling fans in the bedrooms and living space. They had beach towels and beach chairs available for our use as well as a convenient buggy to tote them to the beach if you don’t have or don’t want to use your car. Ample parking spots available and close enough to walk to the Thursday night fish fry and the public beach access. All in all, an extremely positive experience and enjoyable vacation stay. Highly recommend!!

Private house rentals

Guest favourite
Home in Providenciales
5 out of 5 average rating, 31 reviews

Secluded Getaway, Hot Tub & Scenic Water Views

KareeneRating, 5 stars5 days ago
Where do I begin… Dawnett was so pleasant and friendly. She made local recommendations to dine and beaches. The view in the back of the home is amazing. Dawnett cooked us a meal and we chatted. She felt like family or like we knew each a for longtime. There were plenty of towels provided including beach towels. Most Airbnbs usually provide only 1 roll of tissue but there was plenty. We had a wonderful experience, would recommend and will go to visit again.
Superhost
Home in The Bight Settlement
5 out of 5 average rating, 3 reviews

Coconut Cabana 1 King Bedroom

DarianRating, 5 stars5 months ago
Great location and the home was very peaceful, larger space than appeared in photos. Kitchen was very well stocked and grill outside in good condition. Host was very responsive for our few minor needs during the stay. Highly recommend. Our family was primarily here for direct from shore snorkeling and beach activities, which were outstanding. The coral gardens reef is steps away and perfect for young children learning to snorkel for first time. Saw stingray, flounder, lionfish, and of course many common species. For those wishing a more involved snorkeling experience, we saw many sea turtles at smith's reef about 45min walk west along the beach.
Guest favourite
Home in Grace Bay
4.87 out of 5 average rating, 15 reviews

Chez Moi Villa, Beach & Pool

BritinyRating, 5 stars2 months ago
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!
Superhost
Home in Grace Bay
5 out of 5 average rating, 4 reviews

Charming CoCo Gardens -2 bedroom island hideaway

LisaRating, 5 stars47 months ago
Robin and Donna are excellent hosts, who went above and beyond to exceed our expectations! The property is located in a quiet residential neighborhood, which is exactly what we where looking for only a 2 min drive from Grace Bay beach and the city center, with the infamous CoCo Bistro restaurant right around the corner from our villa. Robins Villa is beautifully laid out, very spacious and immaculately clean with a detailed decorative touch in every room to make it feel all the more warm and welcoming. Thanks guys for everything!!! We had an amazing stay and hope to see you again soon!
Superhost
Home in Caicos Islands
4.84 out of 5 average rating, 76 reviews

Colibri Gardens Villa - Great value in Grace Bay

TiagoRating, 5 stars1 month ago
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.
Home in Providenciales
4.79 out of 5 average rating, 19 reviews

Tropical Chalk Sound Cottage with Pool and Kayak!

ErinRating, 5 stars2 weeks ago
We just returned from the most relaxing stay at Silly Creek Cottage—and “relaxing” doesn’t begin to describe it. The view from the deck and poolside was so stunning, we skipped most dinner and day plans just to soak it in. This was our second time in Turks (previously stayed in Grace Bay), and while both spots have their charm, Silly Creek offers a peaceful, private vibe that’s truly special—yet still just 25-30 minutes to town. Jack ,the outdoor cat, was the sweetest surprise—adorable, friendly, and a polite host! (We left food and his new favorite: Bumble Bee tuna.) Kayaking to the inlet at sunrise was magical, and sunsets with wine on the dock were unforgettable. Don’t miss Taylor Bay for crystal-clear, shallow waters and a quiet beach experience. (Under 5 min drive). The hosts were incredibly responsive and helpful. After five nights here, we wished we’d stayed the full two weeks. This place is perfection—we’re already planning our return!
Superhost
Home in Providenciales
4.8 out of 5 average rating, 5 reviews

Sun and Sea Villas (both) - Family friendly Villas

HaleyRating, 5 stars2 months ago
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.
Guest favourite
Home in Grace Bay
5 out of 5 average rating, 6 reviews

#10 The Enclave

DanielRating, 5 stars4 months ago
Will definitely be back! Foluso and Eliza were great to deal with, provided very detailed instructions and Eliza was very timely with check-in and out. Amazing home with great amenities.

Quick stats about house rentals in Leeward Settlement

  • Total rentals

    90 properties

  • Nightly prices starting at

    $206 SGD 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