
Holiday rentals with a patio in Leeward Settlement
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Top-rated rentals with patio in Leeward Settlement
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Popular amenities for rentals with patio in Leeward Settlement
Flat rentals with a patio

Gracebay, Heated Pool, Gated.
Nice place to stay, very clean and responsive host. 10/10 recommend! We will be back.

Island's Eye Twin Bed Studio Room
Rosie was awesome ! Very kind and very helpful.

1 Br Condo | Ocean Vista | Pool
We had such a peaceful time here. Bright sunlit unit with ocean views and comfortable new looking fit out. Owner mentioned to us he had just put in a brand new AC and definitely appreciated how well it worked after some struggles with another unit. And Mike was so friendly and responsive. Thanks for letting us stay at your beautiful condo, we hope to visit again!

Unwind, Swim & Dine Nearby
Eddy was very responsive and helpful, the space was clean and had everything you need (including beach chairs and an umbrella), pool was clean and never crowded, the condo complex was quiet and within an easy drive to restaurants, beaches, and the marinas.

Poolside Tiny House
Wilbert and Christine were wonderful hosts who took very good care of us! They drove us to the supermarket and to the rental car place and always made sure we had what we needed. The best hosts I've ever had on airbnb!

Spectacular view 2 bedroom condo Grandview 205
Truly enjoyed our stay. Very clean property that is represented accurately in their photos. Matthew was an absolute pleasure to work with throughout the process. Location is very quiet. Never had any issues getting a lounger and umbrella at the beach. The pool was comfortable and clean. Overall a great stay.

Blue Mountain Garden TCI 2Bdr Suite
5🌟🌟🌟🌟🌟would never be enough for Our stay at Montbleu . Adriano and his family went over and beyond even before We arrived for Our stay . By the end of Our stay We made lifelong friends and cannot wait to rebook this AirBnb again . We have stayed all over the world & by far this was Our favorite Host & stay . Adriano is amazingly responsive , kind , warm & makes sure everything is perfect every minute of your stay . The accommodation was perfect for my kids & I . The location is amazing close to everything . You have everything you need ( including beach towels / snorkeling / paddle board / chairs ) and if you don’t have something He immediately gets it ( We weren’t missing anything ) . Our stay included gorgeous flowers from his garden as a surprise & a beautiful , thoughtful going away gift . We were truly treated like royalty . Best yet he gives you a million suggestions for restaurants/ beaches / things to do anything you ask you get a reply immediately. Cannot wait to return

Cozy & Relaxing Beach Condo with 2 SUPs
This was a wonderful place to stay and for us... a definite 5 star! Yvetka had all the essentials for enjoying the beach! The condo was comfortable, clean, and had a very workable washer and dryer which was an awesome addition. Loved the kitchen as we brought food with us and also bought food in T&C for cooking! The condo also gets a BIG 5 stars for location, location, location! Fabulous for an easy walk from the condo to the cafe for great coffee (Turks Wave Cafe), wonderful restaurants, and the beach! An easy drive to Grace Beach downtown area. The location was also excellent for getting around the island with our car rental, as we visited many beaches that were mostly within 10-20 minutes away. Highly recommend checking out different beaches as each has it's own character. One of our favorites was Long Bay Beach! Thanx, Yvetka for your quick response to our questions and for sharing your wonderful place! We would definitely come back! Jeffree and Lidija
House rentals with a patio

Beach Landing Villa
Colton and Mallory were gracious hosts. We appreciated the welcome snacks and beverages when we arrived. The beach chairs were super helpful and we loved having the bikes to ride into town for dinner a few nights. While the home is nice, one of the bedroom AC units seemed to have issues the entire time we were there…leaking down the wall and all over the floor. We followed all of the guidelines with not leaving doors or windows open when running it, but I think it needs to be replaced possibly as the other two worked beautifully. And again, nice house and having the pool was a hit with our kids but we paid more than my husband and I think it was likely worth. So much so, I had a hard time enjoying our vacation as I was a bit sick to my stomach we had spent so much for a home on a busy street with construction next door. Again, great hosts but I’m not sure we’d pay that much to stay there 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!

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.

2b/2b BEACH HOUSE STEPS to GRACE BAY! WiFi,AC,Pool
This was a ladies trip and we felt safe and comfortable the whole time! Great communication from the hosts! Very easy walk to the beach and Coral Gardens. The home had everything we needed. AC was great and all beds were super comfortable. The beach gear was wonderful and easy to have! Highly recommend this location. I’ve been to the island many times and always stay on the beach however, this house is only a short walk to the beach and I felt like I was close enough to the beach where it didn’t matter. I would highly recommend!!

Private beach, Pool & Master Suite
We stayed at this beautiful place for our honeymoon. It was the perfect private location with the pool and beach. We used the kayaks and paddle boards provided and enjoyed the beautiful Chalk Sound. My favorite beach, Sapodilla was just a 1 minute car ride / 5 min walk. We will stay here again!

Grace Bay/ New Luxurious home 3+ Bedrooms & Pool
A great place to stay when in Grace Bay! Tons of space with more bathrooms than you’d really need. Was here with 3 friends and we all had our own rooms and full bathroom each, but you could easily have a larger group or entire family stay here. The outdoor area with the private pool was fantastic and the fact that it came with free, easy parking was a great perk. Easily walkable to the beach, however, a car was a good idea to carry things like coolers since the walk is about 20 mins and in the heat there can feel like a lot. Close beach though with easy parking by the beach and no cost to park. Plenty of towels, cooler, etc. included. Only thing I might suggest is having some beach chairs for people to bring to the beach since the sunbeds at the beach are for hotel guests and can be expensive if you aren’t one. Great stay and will most certainly recommend/be back!

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!

Luxe Villa | Infinity Pool, Rooftop & Sunset Views
Absolutely breathtaking! The home and the view were exactly what my husband and I needed for our getaway. Shiri was responsive from beginning to end, and gave great dining suggestions. The property manager, Jonathan, was great as well! We visited Grace Bay and Sapodilla beaches, and found Sapodilla to be our favorite, so Maresia Villa is the perfect location! Hope to visit again soon!
Apartment rentals with a patio

Inn at Grace Bay - Casa Eden
We had a fantastic stay! The location is excellent—just a few minutes' walk to a beautiful, quiet beach with TCI’s turquoise waters, plus shops for groceries, clothes, and gifts and several restaurants, including an excellent Italian spot. The complex is beautiful, with lush gardens and a gorgeous pool that we often had to ourselves. The unit was clean, well-decorated, and exceptionally well-equipped. The kitchen had every appliance and tool imaginable, along with items like tea, coffee, spices, condiments, paper towels, soap, and laundry detergent—far more than other guests we spoke to, who had none of these conveniences. We also had umbrellas and shelter for the beach, avoiding high rental fees, plus coolers and inflatables for the pool. We loved the ground-floor location, making it easy to wander in and out to the pool, and its peaceful spot at the end of the complex. In our opinion, it's the best unit in the complex. Amazing accommodation in a perfect location. Highly recommend!

Grace Bay Hideaway. 1 bedroom, central Grace Bay.
This spot couldn’t be anymore perfect.. A gem seriously. The Airbnb is very spacious, extremely clean, high ceilings, modern, and amazing lighting for pictures :). Comfy bed and pillows. Five minute walk to restaurants, coffee shops, the Ritz, Cocovan, Coco Bistro, Patty Place, and Graceway Gourmet (less than two minutes). Check in and check out was a breeze. The visitor guide provided by Paul was very well throughout and helpful. I did the puppy rescue walk, which was suggested in the guidebook. Truly amazing for the pups. Quick walk down the path to direct beach access. If you don’t feel like lugging the beach chairs and umbrella, you can purchase chairs and an umbrella on the beach for 40 dollars for three hours. Hands down 10/10. I will be returning!!!!!

Crystal Vista Suite
Loved the stay! Easy walk to Shark Bite and Hideaway Cafe. Beach is an easy walk and all the beaches are close drive. Big balcony! Comfortable furniture. Helpful amenities. I cannot hear neighbors. Two pools are great and very close to room. Would stay again.

Amazing GraceBay Views, Pools,Location PH Studio
Lovely 4 nights stay. The beaches are walking distance and so as the restaurants. Robert is so nice and very fast to response. Highly recommended!

NEW! Romantic Getaway, 3 Mins to the Beach !
We enjoyed a week at Mark’s place. Kiki and Mark were great at communicating with us, including helpful recommendations. The location was quiet, yet close to everything in the Grace Bay area. Less than a mile to Sunset Beach which is beautiful and not crowded. Great place to watch the sunset. Would definitely stay here again.

Shore to Please - Large Studio Condo with Patio
Mark’s place was the perfect fit for us! It’s quiet and peaceful, you can see a bit of the ocean from within the studio through the patio. Mark provided great recommendations and was super proactive with all of my questions. It was also great that we got to use the snorkel fins and beach chairs they provided.

Paradise Stay Studio-Beaches-Nature-Relax-Central
Just as advertised. Clean and very close to Smith Reef Beach. as others have mentioned, a car is a must. we had a great trip.

Darcy's place at Golf Course
The condo was exactly as pictured. Clean and comfortable with lots of amenities. The location was excellent with the beach at Rickie’s just a few blocks away and a short drive to shops, restaurants and beaches. Jana was very warm and informative. She was very proactive in her communication and arranged to meet us at the rental unit for check in and check out. Beds were firm and very comfortable, furniture was all in good condition and the place is nicely decorated. The showers had hot water and good water pressure. The AC worked fine. Overall we had a wonderful time at Darcy’s Place and highly recommend this home.
Quick stats about holiday rentals with a patio in Leeward Settlement
Total rentals
250 properties
Nightly prices starting at
₹10,286 before taxes and fees
Total number of reviews
5.4K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
210 properties have a pool
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