Vacation rentals with a pool in Leeward Settlement

Check in was easy. Junior was easy to communicate with. Place was nice. Enjoyed our stay.

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!

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 🤣

This was a perfect spot for a family. We enjoyed the privacy of our own property and pool. The pool deck is its own separate living area. The common space of the house was great for gathering and being together. And the bathrooms and bedrooms were well appointed. The house was extremely well provisioned. The owners thought very well for making the week hospitable. Our family of 7 had a blast here together. It felt like home all week.

We had a wonderful time at the house, it was quiet when we were there, stores and food all walkable distance. There is a wagon with beach toys and chairs also which was a wonderful addition. We had a great experience here. It was clean, cozy and very easy to get to town. GPS took me down the wrong road but host was great at keeping in touch and we figured it out easily it was just one road off not a big deal. I highly recommend this location. The beach at the ritz was our personal favorite

It’s hard to put into words what an amazing trip we had and how much this wonderful place contributed to that. It was quiet, private, and even had a private beach within walking distance. Everything you needed for cooking was in the kitchen, and the rooms are nicely separated for privacy. Our favorite part was Soldier, our island dog, who loved to walk us to the beach every day and was waiting for us when we woke up. The location of this place was great and that it is close to grocery shopping, the airport and some cute restaurants. We will definitely plan to visit again. Great place with great hosts!

We had an amazing stay. The villa is so beautiful and comfortable. It had all the amenities we needed (BBQ, kitchen, beach chairs etc). It was very close to the kitesurfing beach as well as many nice restaurants. The host was very friendly and accommodating. Couldn’t have asked for a better stay!

Wow, wow, and again—WOW! One of the best vacations I’ve ever had! The villa is brand new, beautifully designed, and perfectly equipped. Two spacious bedrooms, each with its own bathroom and outdoor shower, open onto a stunning infinity pool facing the endless blue sea. The open-concept kitchen and living area between the bedrooms offers the ideal blend of privacy and togetherness—perfect for a couple, friends, or family. And the rooftop? A dream for stargazing. Every detail is thought of 3 (!) coffee machines, BBQ, Sonos, beach towels, umbrellas, chairs - you name it. The gated property and beautiful driveway add a true sense of privacy and exclusivity. And Shiri, the host, was amazing! so warm, responsive, and helpful throughout. She gave us great recommendations and even helped us book a jet ski tour that was unforgettable. As a gay man, I felt safe, welcome, and truly at home—Shiri’s allyship meant so much. I’d come back every year if I could. Truly perfect in every way.

Peter was the nicest Airbnb host I have ever had. the unit was very clean and exactly how described. The Villa is very safe and has security that walks around at night time and all around the property has cameras. The unit is one of the best options available at the Villa in my opinion as it is right next to the pool and hot tub. there is a caretaker nearby that can help with anything and he was extremely professional and very responsive when I needed help with the safe. I appreciated that they provided a bolted down safe for our passports and cash. there are several walking distance restaurants, however the host provides a rental car. the rental car place is right next to the Airbnb and they give you a ride back to the airport. the rental car was waiting at the airport for me which was extremely nice. this was definitely my favorite Airbnb experience and I will never forget it.

The place was awesome. Spacious and clean. Jason was a good host.

Our family enjoyed staying at Stephanie’s listing. This was by far one of the best stocked Airbnb’s that we’ve stayed at. Pros- walkable to the beach, well maintained amenities, plenty of pool/beach toys, stocked kitchen, plenty of towels/beach towels, etc., very well thought out list of recommendations (there are several copies at the condo). Recommendations- we rented a car for the whole duration and it was great as we wanted to explore more outside of the immediate area, restaurants are pretty pricey in comparison to in the states so we went grocery shopping for some days and breakfast. I’d recommend bringing refillable water bottles to take with you everywhere as bottled water at places/restaurants will typically cost you $8+ per bottle.

We stayed at Matt & Erin’s for our 10th wedding anniversary and it was amazing! Definitely off the beaten path and remote and peaceful. Their recommendations for excursions, restaurants, and things to do around the island were superb! We loved being able to walk out of the condo straight to the beach and enjoy morning coffee during sunrise! There is some seaweed along the beach but they thoroughly explain that it is for the overall health of the marine/sea life. There are areas not far down the beach that had little to no seaweed. We absolutely loved our time here and will hopefully be back soon!!

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!

Really nice place to stay.

This property and apartment is very clean, with all the amenities needed to make your stay comfortable and feel at home a kitchenette, pool etc. it just walking distance to the pristine sandy beach. Walking distance to bar, restaurants and shopping. I will highly recommend this property for anyone visiting the Island. Drexwell and Rick communicated very well during my stay. Awesome home.

We loved our stay so much we want to figure out when we can come back! The space was great and the location was perfect. The pool was so nice - we rented a car and drive one min to beach access only because we hauled the chairs and snorkeling gear Nancy provided. We felt at home and would stay here again and again.