
Waterfront vacation rentals in Leeward Settlement
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Top-rated waterfront rentals in Leeward Settlement
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Waterfront apartment rentals

Sunny Daze - Condo By the Water
We thoroughly enjoyed our stay, the restaurants within walking distance were some of our favorites even compared to many in Grace bay itself. The morning view and big sliding glass doors were fantastic.

Oceanview Studio: Steps away to Grace Bay Beach
Oscar gave very clear instructions. The place was extremely easy to find and you feel right at home right away. the apartment is stocked with everything you can think of and the view from the balcony is simply amazing. Highly recommend for anyone with a small family or a couple !!

Amazing Secluded 1BR Garden Villa Beach Front+Pool
This is a hidden gem. If you want to unplug and get away, then this is your place. You don't have to leave if you don't want to, this place has everything you need. Grace bay is a short drive also if you want to get out.

Spectacular view 2 bedroom condo Grandview 205
This place is a dream. The views were spectacular, the beach was RIGHT THERE! The pool was nice and never crowded. The set up on the beach was amazing - so many lounge chairs and beautiful white umbrellas. And you could walk to anywhere in grace bay ON THE BEACH. The walk to the Ritz was no more than 15 min for example. I just can't say enough about this place. Also Matthew was fantastic. gave us great recommendations, always attentive. Will definitely be back !

Dorado Duplex: Oceanfront condo
Brads place was a an ideal location for our stay in North Caicos. His co-host, Regine, sent us a lot of useful information in order to best prepare is for our stay. She also met us at the ferry dock and we followed her in our rental car to the property. Regine showed us around and gave us a brief orientation of the condo as well. The property itself is just as described and sits on a beautiful, secluded beach. We felt spoiled with the beauty that surrounded us and were sad to leave. The bedrooms were spacious with AC and beds were comfy. We especially enjoyed sitting in the living room with the screened patio door open so we could hear the sounds of the ocean. Don't hesitate to book of you're looking for a spot on North Caicos. You won't regret it.

Clean and Private Apartment near Beach, Golf, Food
Alanzo was so kind and responded site. He answered any questions we presented and was quite helpful. He offered suggestions for places to see - to eat- and companies to utilize if we wanted to do excursions. He and Charlene have a lovely place with much attention to detail. They have many of the things needed to reside somewhere for a week and want to rest and relax. The beach was close by and easy to access. It was a spectacular holiday and we are grateful that they allowed us to rent their home. I would absolutely recommend their place to anyone wishing to be near the beach but not in the middle of all the hustle and bustle of Grace Bay.

Tara Brezza at Northwest Point
Really enjoyed the condo! It’s a very calm complex with a lot of full time and seasonal residents, so it lacks a touristy feel. Also felt very safe. The beach was good enough and the pool was amazing, and it was very easy to drive everywhere on the island. We thought it was a wonderful value for the price paid too. Pamela was very sweet and welcoming as well. Overall extremely happy both with the property and the island as a whole!

Cozy Beachside Retreat by Chalk Sound Lagoon
The clean and cozy house has a beautiful view of the sound with a private gazebo out back to take in the sunset. Patricia was a great host, very helpful and always responsive. Highly recommend!
Waterfront house rentals

Flamingo's Nest at Whitby Beach (North Caicos)
This was our 4th time at Flamingo's nest with our family of 4, and everything was perfect as always, many thanks to Holly and Hope on making our experience amazing just the same or better than our previous visits. From the detailed instructions and helpful tips on local attractions, to helping out with car rentals and other information, Holly and Hope made us feel like we had a home on North! We can't recommend this place and thank our hosts enough!

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.

Beach-side oasis- heated POOL w/ SLIDE - KING BEDS
What a wonderful gem! The location is absolutely perfect! Description was spot on, a 1 minute walk to one of the prettiest beaches on the island! We are a family of 5 (3 kids age 8,9,12)…all the pool and beach toys and accommodations were perfect for a day at the beach (paddle board, wagon, chairs and umbrella)…there are a couple of beach bars and a restaurant at the other end of the beach, so you can walk down and grab drinks but walk back to the more private end of the beach. The house was great. Anything that popped up unexpectedly (example fire pit was out of propane) Amy was very quick to resolve. Kids all had their own space but we could cook and play game on the balconies as a family. Washer and dryer for laundry was used every day for kids stuff, which was very convenient. Plenty of beach towels for beach and pool days. I would highly recommend this house to anyone looking to enjoy TCI.

Villa View - Sapodilla Beach & Chalk Sound
I loved the closeness to the beach, the views were amazing from all over the house and balcony! We loved the amenities, and felt very safe. Although there was a dock/ work yard nearby that was busy constantly and very noisy, while this didn’t really bother me it could be problematic for a light sleeper. We also went over the electrical allowance with only 2 people, when our trip was originally planned for 4-6 people, we did take advantage of the laundry and cooked in the kitchen. Although we were not excepting a $100+ electric bill at checkout especially considering we were hot in the bedrooms downstairs. I cannot fathom how much we would’ve gone over with more people. (There was a meter the host showed us how to read upon arrival, but he advised us with 2 people we likely wouldn’t go over so we didn’t bother to pay attention to this and apparently should have)

Coastal Vibes Villa Near Sapodilla Beach
The view from the villa is beautiful. It is well appointed, the beds and pillows are very comfortable. The kitchen is stocked with many essentials. They have laundry facilities although we did not use them, we had intended to and then didn’t need to. The view of Chalk Sound is stunning and the beaches within walking distance are definitely the best on the island. We loved the beaches that were close by. Chantal and Dave have chairs and coolers for use at the beach which was wonderful. You definitely need a rental car as it is quite remote from most of the restaurants. Las Brisa’s is right next door which was very handy and we did eat there are few times. The first night on the island we ate there and the food was wonderful. Our next few experiences there were not as good and we wished we hadn’t continued to go back. Thank you for allowing us to stay in your home, it was very relaxing for our family

Luxurious Villa: Amazing Infinity Pool & Rooftop
Fabuleuse Villa!! Tranquille , propreté et que dire de la belle vue . Air conditionner partout! Piscine avec deux chaises dans l’eau! Déjeuner tout les matins sur la terrasse, cuisine complète pour nos repas à la villa. 2 machines café pour débuter matin bu bon pied. Belle plage 3 min de jeep : sapodilla Amener les chaises et parasol que le airbnb nous offre. La literie es propre, les deux salle de bains , le salon et l’extérieur. le rooftop pour prendre un café le matin ou bien regarder les coucher de soleil. Sécurité! Un système alarme et système de barrière. 10-15 min des restaurent en ville WOW!!!

Aventine Villa
Just spent an AMAZING week here and have no complaints! We had 4 college aged teens with us and they loved being close to the water and having access to the kayaks was a HUGE plus. They kayaked everyday and explored the small islands in the sound. The house is located in the more quiet part of the island which we aim for...we like to explore on our own and get immersed in the culture/people of the island. The bedrooms/bathrooms were all great size and perfect for our family. The house was close to 2 amazing public beaches and we felt completely safe the entire time. For those that are nervous, the house comes with a home alarm system. They had beach chairs/umbrellas/snorkel gear there for your use and they really helped us out. Would recommend this house to anyone interested.
Waterfront condo rentals

Beachfront condo at Northwest Point
Ana's place was clean, spacious, and well equipped. We really appreciated having some beach equipment (small cooler, umbrella, beach chairs), and the resort's paddle boards and kayaks. The pool is great, the area is quiet and peaceful, and we felt like we had a private beach!! Of note, there was no laundry detergent and there is quite a bit of sea grass in the water. You can walk a little ways down and avoid it, or keep going and find the national park with some cool sights and beaches. Definitely need a rental car, and groceries here. Was perfect for our family, who like to avoid the heavy touristy areas and really explore the location, not just sit on the beach the whole time.

Ocean view paradise
The condo was perfect for the two of us. The location is central to everything and felt really safe throughout our stay. It’s only a short walk to the beach and great snorkeling spots, nice restaurants, and the view from the condo is just amazing. The bed was comfy, had all the basics in the kitchen and bathroom, and all the beach equipment you could ever need! Evelyne, the site manager was so accommodating that it made our stay even more enjoyable. Honestly couldn’t have booked a better place in TCI.

Ocean and Pool Front 2 Bedroom 2 Bath Condo
Beautiful, secluded. We would walk about 6 minutes to a more turquoise part of the private beach free of seaweed. We didn’t have a chance to try the on site restaurant or bar. Having a kitchen was nice to make our own breakfasts. Make sure to stop and buy your own sugar, cream, and coffee. Used coffee machine everyday. Very clean place. Comfy bed. Drawers for storage. Water was always hot even when two people showered at the same time. Ate at the Coralli at the Ritz Carlton for lunch right on the water and it was delicious. Also loved “farm” at Seven stars resort. Provali Neapolitan pizza is small but incredible!!! Host Jasmine was great and very responsive. The pool was never too busy and neither was the beach which we absolutely loved! Had the whole beach to ourselves most days! Also shopped at a local shop in Grace Bay called lemon 2 go and got some wonderful smelling perfumes and reed diffusers. Would definitely come back.

Sanctuary by the Sea
This may have been the most enjoyable Airbnb stay we've ever had. Regine was a superstar. She met us at the ferry port, helped facilitate our rental car and personally escorted us to the condo. She thoroughly walked us through everything we needed to know about North Caicos and the condo. The condo was clean and had everything we could needed and more. There was a box filled with sunscreen, bug spray, beach chairs, towels and more. It's location was beautifully located on Whitby beach, which was our favorite beach of the trip. I have nothing but great things to say about our experience. Thank you Regine!

Coral Condo on Grace Bay Beach
Allyson was very responsive and quite helpful during our stay. The condo is immaculate with great amenities. At low tide we walked into the beach at the property and saw many fish all around us without any snorkel gear. The construction noise next door can get loud on the balcony, but generally inside it is quiet. The two pools and onsite cafe were wonderful surprises.

Luxury Large 2 Bed 2 Bath at the Yacht Club
The location is fantastic—quiet, scenic, and close to a couple of great local spots. The condo itself was clean, well-maintained, and we felt very relaxed the moment we arrived. Courtney was incredibly helpful and responsive in the lead-up to our trip, and once we arrived, we were warmly welcomed by Molly, the property manager. Molly made everything seamless. We arranged for the fridge to be stocked before our arrival which was a great way to start the trip. We had a small issue with the car (a tail light wouldn’t turn off), and Molly had it taken care of promptly the next morning. The Yacht Club’s pool is beautiful and meticulously kept, and we really enjoyed meals at nearby Shark Bite and Baci—both were great and more reasonably priced than some of the Grace Bay spots. A close walk to the public beach (there is parking) and Smith's Reef as well. Rec. Sapodilla Beach for calm, shallow and gorgeous water. Highly recommend and can't wait for our next trip back!

Bliss Ocean Beach Condo, Whitby, North Caicos
The condo was on one of the most beautiful beaches I have ever stayed at. If you are looking to get away from it all, I highly recommend this place. Marilyn was responsive and took great care of us. The internet was perfect for remote work and the house had everything we needed.

Luxury Condo Somerset on Grace Bay!
Had a wonderful time!! Mark and Kiki were great host to my fiancé and myself. Grounds were beautiful including the pool and the beach was just a short walk past the pool, which led to one of the most beautiful beaches I’ve ever seen! We decided to extend our stay at very short notice and Mark was able to let us stay and enjoys couple more days. If we had any questions at all they were answered promptly and went above and beyond!! I would highly recommend Mark and Kiki’s properties and would be happy to book with them when we visit in the future!!
Quick stats about waterfront rentals in Leeward Settlement
Total rentals
60 properties
Nightly prices starting at
ﺩ.ﺇ771 before taxes and fees
Total number of reviews
910 reviews
Family-friendly rentals
60 properties are a good fit for families
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Grace Bay Vacation rentals
- Grand Turk Vacation rentals
- Long Bay Hills Vacation rentals
- North Caicos Vacation rentals
- Long Bay Beach Vacation rentals
- The Bight Settlement Vacation rentals
- Chalk Sound Vacation rentals
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- Rentals with a kayak Leeward Settlement
- Rentals with a fire pit Leeward Settlement
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