Vacation rentals with a pool in Leeward Settlement

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.

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

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 🤣

We really enjoyed our stay. It was a great location & walkable to beach, grocery & restaurants.

The house was perfect for 3 of us over Spring Break, having the beach chairs, umbrellas, cooler and snorkellng gears were a huge help. We loaded up the car everyday and headed to our favorite Leeward beach. The house was in a quiet area with a fence gate. Coconut Bistro was the nearest restaurant and was walkable but for more restaurants/shopping it would be maybe 15-20 mins walk, luckily we had a car. We had a great time on this beautiful island and would love to come back one day.

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!

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!

Absolutely perfect stay! This place exceeded all our expectations — beautifully decorated, spotless, and just steps from the beach. The hosts were incredibly responsive and thoughtful, making sure we had everything we needed for a relaxing getaway. Can’t wait to come back!

Ulma’s place was perfect! The central location to everything was great since we went everywhere. At the house they had beach chairs, coolers, umbrellas, snorkel gear and quite a bit of other items we did not use. The pool was basically right out the back gate! The AC worked wonderfully, the house was stocked with everything we needed, it was incredibly clean, and the lay out for us was great. Highly recommend staying here!!

Jason's place is very nice, clean, and comfortable. We really enjoyed our stay. He was attentive to us the whole time, asking if we needed anything. The restaurants and beaches are very close. We will definitely go back.

Loved staying here and would absolutely rent again. The place has everything you need for a stay, and it's great central location for exploring the island. The condo is quiet, spacious, and clean. The view from the balcony patio is gorgeous! The pool is fabulous. The nearby restaurants are good, you can walk to get a coffee in the morning if you don't make your own. This place has all the extras that elevate your beach vacation: in-unit washer and dryer, beach chairs, beach umbrella, cooler. He even provides a bucket you can fill with water to wash the sand off your feet before entering the unit. I had to leave my reservation early due to a family emergency and the local manager was immediately responsive and kind. I can't wait to stay here again!

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!!

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.

Great location in Turtle cove, one block from Marina for diving! Gemma was very accommodating and flexible, which was great with our schedule! Check out Viator website for activities! Definitely need a rental car for transit on the island!

Marcia’s condo was perfect for a quick getaway! The location was perfect and we were 10mins from the main attractions. We really enjoyed our time there and will be back to visit.

We had a great stay at La Vista Azul. Roberto was super attentive and gave us great recommendations so we knew how to plan our vacation. We loved the location it was easy walking distance to a few great restaurants, we could easily walk to Smith’s reef from this location for some great snorkeling (and turtle sightings) , and the location made it easy for us to travel to all of the beaches we wanted to see. It was a very quiet location and felt very safe with a gated entrance and security guards on site. The pools and views were amazing! I would absolutely return to this location and highly recommend Roberto as a host.