
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!
Junior's place was as described. Ideal location with convenient features, we enjoyed our stay. ACs in the living room and bedrooms were good. Kitchen had plenty of utensils for us to use. Hosts were very responsive to all our questions, queries and requests. They even got us a replacement beach umbrella ! Thanks for having us Junior

2 BR Ocean View- Private Pool- Flame Tree Villa #2
Our stay at Eric’s property was absolutely phenomenal! The property is a perfect blend of modern elegance and cozy comfort, with stylish decor, plush beds, and a spotless, well-maintained space that felt like a luxury retreat. The fully equipped kitchen, high-speed Wi-Fi, smart TV, and serene outdoor area with a pool were just a few of the standout amenities that made our stay effortless and enjoyable. Every detail, from the pristine cleanliness to the thoughtful touches like fresh pastries delivered every morning was excellent. The kids were looking forward every morning to checking to see if Eric had dropped off the pastries! The location was ideal, offering easy access to the beaches (Grace Bay beach etc), restaurants, and shops while maintaining a peaceful atmosphere perfect for relaxation. The Eric’s outstanding communication and warm hospitality elevated the entire trip, even accommodating check out preference. We highly recommend this gem to anyone. You wont regret it!

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.

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!
Condo 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!!

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.

🏖🏝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!

Grace Bay Luxury Gated 1400 sq ft 2 Bedroom Condo
James was very responsive and left clear instructions for us. The Airbnb was the cleanest we have ever stayed in, and the location is perfect. Slightly away from the hustle and noise of the main resorts but still within 5 min walking distance to the beach and plenty of restaurants. The Turks Kabob and CocoVan are quick, inexpensive places to get food and the resort restaurants and Coco Bistro. The grocery store across the street has everything you need and was the deli there was very economical for lunch food. We were very happy with our stay!

🌴 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!

Amazing GraceBay Views, Pools,Location PH Studio
Roberto was a fabulous host and his place was just what I needed! Great location, clean, spacious, tons of amenities and safe. Roberto was very quick to respond to any inquiries I had prior to my trip and while I was there. He had lots of great recommendations for spots to check out yummy places to eat and more! If you need a place in TCI to stay, Roberto’s is it! I will definitely be back for another stay. Thank you again, Roberto!

Sea Dreams - Jr 1 bdrm with Panoramic Ocean views!
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!
Quick stats about holiday rentals with a pool in Leeward Settlement
Total rentals
280 properties
Nightly prices starting at
$182 NZD 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
- Grace Bay Holiday rentals
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