Some info has been automatically translated. Show original language

Holiday rentals with a pool in Leeward Settlement

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Leeward Settlement rentals with a pool

House rentals with a pool

Guest favourite
Home in Grace Bay
4.92 out of 5 average rating, 113 reviews

Tropical Carabas Villa!

AlbertRating, 5 stars1 month ago
Check in was easy. Junior was easy to communicate with. Place was nice. Enjoyed our stay.
Guest favourite
Home in Grace Bay
4.88 out of 5 average rating, 110 reviews

Gated Villa w Pool. Walk to GraceBay Beach & Shops

MicheleRating, 5 stars6 days ago
We really enjoyed our stay. It was a great location & walkable to beach, grocery & restaurants.
Top guest favourite
Home in Providenciales
5 out of 5 average rating, 22 reviews

2 Bedroom Spectacular Views

MissyRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in TC
4.98 out of 5 average rating, 182 reviews

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

AllisonRating, 5 stars1 month ago
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!
Guest favourite
Home in Islands
4.99 out of 5 average rating, 106 reviews

The Sapphire Villa. Tropical Oasis. Make memories

ZhenghaoRating, 5 stars2 weeks ago
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!
Superhost
Home in Providenciales
4.91 out of 5 average rating, 107 reviews

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views

SafieddineRating, 5 stars5 months ago
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.
Superhost
Home in Providenciales
4.87 out of 5 average rating, 39 reviews

Caya Villa 2 - 2 Bedroom View Attractions

ChristinaRating, 5 stars5 months ago
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.
Superhost
Home in TC
4.88 out of 5 average rating, 126 reviews

Sea More Getaway

Stephanie Rating, 5 stars1 month ago
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

Top guest favourite
Apartment in Turtle Cove
4.93 out of 5 average rating, 114 reviews

Allies Rest - Seaflowers townhome

DeannaRating, 5 stars1 week ago
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!!
Guest favourite
Apartment in Turtle Cove
4.95 out of 5 average rating, 180 reviews

🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝

ChasityRating, 5 stars4 days ago
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!
Guest favourite
Apartment in Turtle Cove
4.9 out of 5 average rating, 108 reviews

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

ErinRating, 5 stars1 month ago
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.
Superhost
Apartment in Providenciales
4.95 out of 5 average rating, 191 reviews

Amazing Ocean views -Modern Condo -Balcony - Pool

AprilRating, 5 stars1 week ago
Jacinthe was a great host and her condo was gorgeous! Very responsive to any questions and accommodations I had, definitely will book again!
Guest favourite
Apartment in Providenciales and West Caicos
4.87 out of 5 average rating, 441 reviews

🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞

KorrieRating, 5 stars1 day ago
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.
Guest favourite
Apartment in Wheeland Settlement
4.95 out of 5 average rating, 124 reviews

Couple’s Retreat with ocean view,pool and hot tub!

Roxanne FaithRating, 5 stars1 month ago
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!
Guest favourite
Apartment in Turtle Cove
4.98 out of 5 average rating, 110 reviews

Shore to Please - Large Studio Condo with Patio

ChuchuRating, 5 stars2 months ago
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.
Superhost
Apartment in Turtle Cove
4.81 out of 5 average rating, 132 reviews

Paradise Stay Studio-Beaches-Nature-Relax-Central

MarieRating, 5 stars1 week ago
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