Villa vacation rentals in Leeward Settlement
Find and book unique villas on Airbnb
Top-rated villa rentals in Leeward Settlement
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Leeward Settlement villa rentals
Private villa rentals
Villa in Leeward Settlement
4.98 out of 5 average rating, 55 reviewsUnique, Modern Cozy & Private | 2 minutes to Beach
The villa was very comfortable and clean. I appreciated the yoga mat and weights for daily exercise routine. There are Smart TV’s in bedrooms to catch up on your Netflix programs and a regular TV with cable stations in the main room. The pool was wonderful, clean, refreshing. Lots of white, plush bath towels and beach towels in lovely bathroom areas in both bedrooms. We love the Leeward location because it is quiet and off the beaten path yet easy to access downtown and Grace Bay Beach. A rental car is necessary. Pelican Beach is a quick drive away or an easy walk. The beach is absolutely beautiful with awesome sunsets … My husband and I had a wonderful, restful vacation in this well appointed villa. Rochelle was easily reachable to answer questions and responded promptly.
Villa in Providenciales
4.96 out of 5 average rating, 69 reviewsSapodilla Bay - Walk to the Beach!
I stayed at Ari’s place with my husband for our first time in TCI. The place matched the photos and was very clean. The only issue we ran into was that the villa had somewhat of a musty smell, the outdoor shower only got to room temp, and indoor shower was extremely hot. None of these “issues” bothered us enough to ask the host to come by for a fix. The bed was very comfy and the pool was nice to have. The host wasn’t sure what toiletries/amenities were available so we did come prepared with our own soap etc although it wasn’t needed. The Chalk Sound/Sapodilla Bay Area of the island is a true gem. We used the beach cart available and brought the cooler and towels to the beach for the five min walk. It should be noted that the host does not provide beach chairs. There are two captain’s chairs, but these are not really suitable for lounging on the beach. Thus, we rented loungers from the vendors each day for $20. Overall I highly recommend this place and we would love to return someda
Villa in Providenciales
4.92 out of 5 average rating, 52 reviews‘My Little Hideaway’ at Lucayan Cays
Tiajuana’s place was beautiful!! She gave us so many ideas and recommendations on where to go to eat and affordable places on the island. Tiajuana was quick to respond and made sure to check up on us if we needed anything. The place was clean and perfect for us newly weds. The views from the house are beautiful and is right in front of the ocean. Loved how private the house is from everything , it felt very safe and peaceful. Would definitely stay again!
Villa in Long Bay Hills
4.97 out of 5 average rating, 29 reviewsOcean Dream Studio Blue
Ocean Dream was amazing! The location is perfect, right on the water in a quiet section of Long Bay but still incredibly close to downtown Grace Bay, beautiful beaches, and restaurants. The studio was beautiful, even better than the photos. Great stay all around, we will definitely be returning to this property. Tip: Having car is a major plus rather than having to rely on car services.
Villa in Providenciales
4.96 out of 5 average rating, 52 reviewsRockspray Villa | On Point in Ocean | Waterfront |
We LOVED this place!!! It was exactly what we hoped it would be!! Very private and the view is incredible!! Just like the photos and MORE!!! We enjoyed the deck with amazing scenery every single morning, through out our day and every single evening!!! The two nearest public beaches were beautiful and within walking distance too!! We also had a couple of nearby restaurants we went to a few times as well!! We were looking for a beautiful, peaceful, private and relaxing time and we got that at Rockspray!!! The home was absolutely beautiful and had everything we needed! We also LOVED going out on the kayaks they provide!!! I would also like to add that the hosts were excellent about responding when we needed something and extremely helpful!! Also very kind when we had a mix up getting a rental and were a little late getting to the place our first day. Excellent hosts for sure!!! Thank you for a perfect 10 year anniversary location, home and view with Rockspray!! HIGHLY recommend!!!!
Villa in Long Bay Hills
4.81 out of 5 average rating, 16 reviewsThe Haven
Wonderful place and hosts! They really were responsive and thoughtful. We had a wonderful time at the AirBnB. Would come back
Villa in Providenciales
5 out of 5 average rating, 14 reviewsSardinia- Beach front Luxury Villa
Our stay at the SulMar Villa was wonderful. Jillian and staff were exceptional. We visited October 2024. The Villa is very clean and stocked with all the amenities needed. We went the IGA grocery store and stocked up for the week. We grilled a few evenings and it was so perfect. The upper balcony is perfect for morning coffee and watching the sunset with a glass of wine. The Villa sits directly on Taylor Bay Beach which is less than .50 miles long and shallow . You can walk out to where it meets the ocean. The kayak & paddle board was a lot of fun. We kayaked around the corner to the left & hugged the shore line which was shallow as well. Enjoyed looking at the homes along the ocean and was able to view Sapodilla Beach. The location is very secluded. When you drive anywhere you are driving with the locals who drive very fast. There's not a lot around the area. The Brewery is fun to visit and Omar's. You will need to drive over to Grace Bay for shopping & restaurants.
Luxury villa rentals
Villa in Providenciales
5 out of 5 average rating, 49 reviewsWALK TO BEACH IN 2! RECLINE … RELAX … RECHARGE …
Mandy's home is the most perfect location on the island. My boyfriend and I love Sapodilla Bay. I was thrilled to find Sapodilla by the Sea. I could not believe the beauty of the home and neighborhood. We were overjoyed when we pulled into the driveway. There are gorgeous trees and flowers and spacious parking. The deck was pristine and pool was so inviting. We used the barbeque a few nights as well and were able to enjoy the outdoor table. Inside was immaculatey clean and had some many amenities. We appreciated having laundry as well. The beds were very comfortable. We loved walking to the beach. Mandy provided a wagon, chairs, umbrellas and various floats. It was a very short walk to the beach. Mandy was very reponsive and provided info about medical care as I had ear pain from the airplane. She provided many recommendations for places to eat and activities available. We had a fantastic stay. We hope to get back to Sapodilla by the Sea in the future!
Villa in Providenciales
4.97 out of 5 average rating, 35 reviewsVilla Bashert
The view was absolutely incredible in this clean, peaceful, private sanctuary. So many separate areas to sit and relax outside provided variety throughout the week with the opportunity for everyone to relax and read or gather to hang out. Sleeping accommodations, linens, pool, kitchen were all top notch. The drive to Grace Bay wasn't bad, but if you're looking for a social scene, this is not the area (think private luxury with a fantastic beach across the street). We swam in the Sound and the pool daily and loved both (shallow water in the sound, but we were fine with that). Property manager great. Traveling with 3 teenage sons and all gave 2 thumbs up. We hope to return!
Villa in The Bight Settlement
4.96 out of 5 average rating, 27 reviewsVilla Blu - A contemporary 3 BDR/BTH Villa minutes
Our stay at Villa Blu was perfection! Our trip was 5 girls for a birthday celebration and the accommodations were on point! The walk to the beach along with the beach accessories was a HUGE highlight. George our concierge was lovely, fast to answer texts and offered local recommendations. We also appreciate told the suggested taxi driver, made us feel safe knowing this person was recommended and he was there whenever we asked. The kitchen was fully stocked, we were able to have breakfast everyday at the villa and a few grilled dinners. If I ever get to return to Provo I would 100% stay here.
Villa in Providenciales
4.84 out of 5 average rating, 81 reviewsBeachHaus Villa with ocean view and private pool
Dallas was an incredible host and had a stunning place. His house has a great layout and is so private. Our kids loved the pool, it was a great spot to just relax and enjoy our time in the sun. Walking to the beach was easy, and you weren’t far from amenities. Everything was intentional, and available. We loved the kitchen and had some meals sitting around the island, enjoying family time. We loved the primary bedroom with its vaulted ceilings, our own ensuite and beautiful balcony. Our kids loved their rooms and their gorgeous bathroom. We enjoyed movie nights with the huge TV and cozy couch and blankets. Having laundry was extremely helpful for us. Dallas gave us incredible recommendations and truly made our experience off the charts! He went above and beyond and we would absolutely stay there again! Also a very private, quiet and serene location which was what we were looking for! Thank you Dallas!
Villa in Long Bay Hills
5 out of 5 average rating, 28 reviewsHang Five Surf Villa in Long Bay
My family and I really enjoyed our time at Katie's place. The location was private but still close to great beaches and restaurants. The place itself was clean and organized with great amenities. Katie provided great instructions/recommendations and she was very responsive. The only downside was the ongoing construction around the property. Overall 10/10 would definitely recommend this place to anyone coming to beautiful Turks and Caicos!
Villa in Cooper Jack Bay Settlement
4.93 out of 5 average rating, 15 reviewsVilla Tayo Canal Front with Pool 5BR
Brian is AMAZING! We could not have picked a better home or location for our very first visit to Turks. Our group enjoyed the home’s amenities and the fact that it was close to all the places we chose to visit! We had an unforgettable trip! We 5would definitely come back and stay at Villa Tayo! Thank you Brian! 5Star all the way!
Villa in Providenciales
4.98 out of 5 average rating, 86 reviewsVilla Jayla
A breathtaking view! Everything is perfect! The location is amazing the excellently well-equipped kitchen the kayaks allowed us to discover the surroundings. Every morning and night we had two rays that visited us by the dock. A little further by kayak we could observe the turtles. A bonus for the bedding we found extraordinary. Really a dream spot!!
Villa in Grace Bay
4.85 out of 5 average rating, 13 reviewsCoco Palm Villa
Wonderful experience from check in to check out. Brian was great with anything we needed. He even cut down coconuts for us from the tree. The airbnb was very clean, safe, and had everything we needed including a cooler we took to the beach and beach towels. Location was great as it was walking distance to the beach and we had access to beach chairs and umbrellas right on the beach in the front. Highly recommend staying here.
Villa rentals with a pool
Villa in Venetian Road Settlement
5 out of 5 average rating, 3 reviewsFlamingo Lake view villa at Harbour Club Villas
Marta's place was just what we wanted for a nice getaway...peaceful, beautiful view of the lagoon, short drive to the beach, a great space to relax. We sat out in our own little private space/chairs each day for a bit, morning, afternoon, and night, enjoying the views and weather. Bob's Bar is a short walk away, with good food and drinks, and is a perfect spot to watch the sunset. Marta greeted us as we drove in and showed us around the place, making sure everything was in order and that there was nothing else we needed. She also arranged a local car rental for us, which included a pickup from her spot in the end to drive us to the airport. She was an amazing host, giving us local recommendations on the first day and available the whole time for any questions. We highly recommend staying at her place, and we hope to be back ourselves!
Villa in Whitby
4.75 out of 5 average rating, 12 reviewsPelican Beach Villas 2
This Airbnb was incredible. The host was amazing - responsive, friendly and so helpful! One of the guests in our groups had been to North so had a really good idea of what we’d be getting into - but exceeded all expectations! We were the only people on the beach and it was so peaceful and relaxing!! A few helpful tidbits for north newbies - grab groceries on Provo before coming over (we brought cooler bags and bought ice for transport) and got all of our water from the local store and filled up throughout the week, went out on captain D’s boat (excellent)! Try to bring an umbrella (zero shade by the pool) and bug spray when lounging by the pool (which is expected). AC worked great and we were up with the sun (curtains were thin) but that’s was fine by us, we just made sure to go to bed early. Can’t say enough great things about this place! But if you are looking for fancy touristy resort, stay on Provo (please), if you want relaxing paradise - come to North but keep it a secret 🌴
Villa in Grace Bay
4.75 out of 5 average rating, 20 reviewsThe White House TCI Guests house
This surpassed my expectations. It was perfect for the entire family including the kids. I will definitely be rebooking in the future.
Villa in Leeward Settlement
5 out of 5 average rating, 4 reviewsNew Listing! Modern Comfort! Private Pool!
My family stayed at this beautiful property for a “bucket list” vacation. It couldn’t have been more perfect…great location and close to the grocery store, awesome restaurants and most important Grace Bay beach. We were never more than 20 minutes from anywhere we wanted to visit. The property was more than we had expected. The kitchen was fully stocked with everything needed. There were ample amounts of bath and beach towels. The outdoor patio and pool area were beautiful, private and quiet and we really enjoyed it after a day at the beach and before dinner. We really appreciated having 4 beach chairs and 2 umbrellas for the beach. The beds were probably the most comfortable we have ever slept in ! Wendy and Bianca were very responsive throughout the whole process and whenever we had questions. Bianca stopped by after we had arrived to welcome us, which is something we have never experienced with other properties. I would highly recommend staying here…you won’t be disappointed !!!
Villa in The Bight Settlement
5 out of 5 average rating, 18 reviewsWalk to Grace Bay Beach ~ 3 bedroom en-suite
Beach Please Villa was excellent and Stephanie was a tremendous host providing lots information and suggestions for chefs, restaurants and a car service as well as things to make sure we see. The villa was very well appointed, comfortable and perfect for a birthday celebration! We will look to book another trip to T&C and at Beach Please! I should awesome beach with excellent snorkelling right of the beach!!
Villa in Providenciales
4.76 out of 5 average rating, 46 reviewsCanal Front Luxury Villa!
We had the pleasure of staying at this breathtaking Villa nestled right on the water, and it was nothing short of amazing. From the moment we arrived, we were captivated by the serene beauty of the surroundings and the impeccable design of the property. The location was perfect for us as we were seeking tranquility and natural beauty. It sat right on the edge of the canal, offering panoramic views that truly took our breath away. The accommodations themselves were equally impressive. The interior was elegantly furnished with a blend of modern amenities and cozy touches that made us feel right at home. The bedrooms were spacious and comfortable, with large glass doors in the master bed that allowed for stunning views of the water from the comfort of my bed. Lori's hospitality was exceptional. She paid attention to detail and was ensured that all our needs were met. A beautiful home away from home that we can't wait to book again! Thanks for everything Lori, you made our stay memorable!
Villa in Long Bay Hills
4.71 out of 5 average rating, 7 reviews4BR 4Bth: ocean view, walk to Long Bay Beach, pool
Karen and Jack were very welcoming. They were sure to check in on us through the week to make sure our stay was amazing. The house was beautiful and we sure wasn't ready to leave it yet😔. If you're visiting Turks this is the house and host you would want to book with! Thank you again Karen and Jack!!!
Villa in Providenciales
4.94 out of 5 average rating, 16 reviewsTurks & Caicos Oceanfront Villa w/Pool and Dock
I’ve stayed at many places and this was by far my favorite house. There is a gorgeous view from every room. We used the kayaks and paddle board and the water was perfect for my 11 and 12 year old to swim and we saw fish! Las Brisa’s restaurant is down the street with amazing food all day, gas station close with everything you need, and Chalkies delivers yummy food to the house. The house is private and has parking and amazing air condition. 3 bathrooms and omg the pool was incredible with the changing lights. We really didn’t even need to leave this house and if I ever go back I will stay here again.
Quick stats about villa rentals in Leeward Settlement
Total rentals
140 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
130 properties are a good fit for families
Rentals with a pool
130 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
- Grace Bay Vacation rentals
- Grand Turk Vacation rentals
- Taylor Bay Vacation rentals
- North Caicos Vacation rentals
- Long Bay Beach Vacation rentals
- Sapodilla Bay Vacation rentals
- Chalk Sound Vacation rentals
- Turtle Cove Vacation rentals
- Salt Cay Vacation rentals
- Santo Domingo Vacation rentals
- Santiago de los Caballeros Vacation rentals
- Las Terrenas Vacation rentals
- Villa rentals Turks and Caicos Islands
- Villa rentals Providenciales
- Villa rentals Grace Bay
- Rentals with a kayak Leeward Settlement
- House rentals Leeward Settlement
- Rentals with a washer and dryer Leeward Settlement
- Rentals with a fire pit Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Family-friendly rentals Leeward Settlement
- Apartment rentals Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- Luxury rentals Leeward Settlement
- Beachfront rentals Leeward Settlement
- Fitness-friendly rentals Leeward Settlement
- Rentals with a fireplace Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with beach access Leeward Settlement
- Pet-friendly rentals Leeward Settlement
- Monthly Rentals Leeward Settlement
- Rentals with pools Leeward Settlement
- Waterfront rentals Leeward Settlement
- Villa rentals Caicos Islands
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes