
Holiday rentals with a pool in Leeward Settlement
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Top-rated rentals with a pool in Leeward Settlement
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Popular amenities for Leeward Settlement rentals with a pool
House rentals with a pool

Tropical Carabas Villa!
Check in was easy. Junior was easy to communicate with. Place was nice. Enjoyed our stay.

Gated Villa w Pool. Walk to GraceBay Beach & Shops
We really enjoyed our stay. It was a great location & walkable to beach, grocery & restaurants.

2 Bedroom Spectacular Views
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!

“The Lighthouse”, Private Pool, Ocean Views, Beach
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!

The Sapphire Villa. Tropical Oasis. Make memories
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!

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views
Sea la vie is a quiet and relaxing place. The unit is as advertised and super clean. The long bay beach is a few minutes walk from the property has beautiful sunrise, paddle board, kayaks, portable chairs and umbrella are complementary by sea la vie.Majid the Host was helpful to answer any question we had.

Caya Villa 2 - 2 Bedroom View Attractions
We stayed in Caya Villa 2 for 1 week. The house is beautiful & exactly as shown in the pictures. It was spacious, comfortable & clean. They even provided a mid-week cleaning which was great. The bathrooms are awesome & the mattresses are comfortable. The location was decent. It is just a short 10 minute ride into the heart of Grace Bay. However, several of the roads are not paved & there are a fair amount of stray dogs. Although the house is so close to Long Bay Beach, there is no access to the beach (unless you drive for 10+ minutes), so we could not walk to the beach. The major disappointment was that we could not use the beautiful outdoor spaces of the house as we expected because the no-see-ums were really bad (we each had bw 60-100 bites) & the pool was not heated. There is a lot of vacant land in the neighborhood with overgrown vegetation which must contribute to the bugs. The pool was simply too cold for my kids (I was okay w/the temps). Overall, we had a nice week.

Sea More Getaway
I would like to express my sincerely gratitude. This was the first time I stayed at an Airbnb in Turks. It was wonderful foe my family and I. The place was well stocked with amenities and we utilized all the offerings. From the kitchen, to the pool, to the laundry area. Thank you so much!
Apartment rentals with a pool

Allies Rest - Seaflowers townhome
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!!

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝
We had a wonderful 7-day stay at this spacious and clean condo in Turtle Cove. Traveling with two teenagers and a friend, we found there was more than enough room for the four of us to relax comfortably. Very minimalist vibe, which I love. No clutter! The condo was very well-equipped with everything we needed—including a coffee pot, tea kettle, air fryer, toaster, beach towels, chairs, and floats. One of our favorite features was the balcony overlooking the pool—it was perfect for keeping an eye on the kids while enjoying the beautiful view of the ocean. Safety was also a priority for me, especially traveling with only women and children. I really appreciated that the gates remained secured 24/7 with access by code, and that there was on-site security each night when we returned. It gave me peace of mind throughout our stay. Overall, we loved our experience and would definitely recommend this condo to anyone visiting the island!

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED
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.

Amazing Ocean views -Modern Condo -Balcony - Pool
Jacinthe was a great host and her condo was gorgeous! Very responsive to any questions and accommodations I had, definitely will book again!

🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞
Condo is in a great location. Was very quiet. Walking distance to a couple of restaurants. Had everything we needed for our week long stay. Would recommend a car though to see & explore other places.

Couple’s Retreat with ocean view,pool and hot tub!
We felt comfortable and at home in Matt & Erin’s place. It was clean, had everything we needed and very private. It was off the beaten path which is exactly what we wanted. The location is perfect. The private beach is unmatched. The pool being right in front of the condo is perfect. There is a hot tub as well but we didn’t use it. Matt is very responsive and accommodating. We would love to stay with them again. Thank you, Matt & Erin!

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
We enjoyed staying at your place. Clear and accurate directions were provided so it was easy to find. The place was clean and close to local restuarants and shops Would definitely stay here again!
Quick stats about holiday rentals with a pool in Leeward Settlement
Total rentals
280 properties
Nightly prices starting at
₹9,520 before taxes and fees
Total number of reviews
4.9K reviews
Family-friendly rentals
230 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Destinations to explore
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