
Holiday rentals with outdoor seating in Leeward Settlement
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Top-rated rentals with outdoor seating in Leeward Settlement
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Popular amenities for outdoor seating rentals in Leeward Settlement
House rentals with outdoor seating

Beach Landing Villa
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.

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

Hopewell Villa East/Pool & walk to Gracebay Beach
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.

“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.

2 Bedroom Stunning Views
Beautiful location and overall an amazing place to stay if your looking to relax and enjoy the views.

Vision Kite- Longbay beach house
Wow! This place was perfect for my husband, myself, and our one year old. It’s so close to everything and allowed us to easily jump around to all the different beaches. The house is stunning and view is to die for! Highly highly recommend!!! Also, David is really great to rent from. He was super helpful and flexible with us, which were super grateful since we had our son with us and babies need flexibility ha! Thank you so much for such a wonderful experience!!!
Apartment rentals with outdoor seating

OCEAN ORCHID
Ocean Orchid was absolutely amazing. My family (wife, 4 y/o and 3 mos old), plus grandparents, stayed here for a full week. Nearby beach is super peaceful (like no one ever) and great for little kids. The backyard pool and sandpit was a big hit with our oldest, who just couldn't get enough of the table in the water and the big boat. Won't lie, I had fun watching the fish from the infinity pool. Karen was a wonderful host. Went above and beyond A+ hospitality. Upon arrival, there were some great snacks. She even went out and got us some super soft linens and an infant bath chair for our baby. All in all, would highly recommend staying here. Great location if you want to be away from the hussle and bussle, but still 15-20 minute to anything on the island, clean and always cool inside. Views were great from the decks (yes, two decks). If this is available during your travels, don't hesitate.

Gracebay, Heated Pool, Gated.
Nice place to stay, very clean and responsive host. 10/10 recommend! We will be back.

Unwind, Swim & Dine Nearby
Eddy was very responsive and helpful, the space was clean and had everything you need (including beach chairs and an umbrella), pool was clean and never crowded, the condo complex was quiet and within an easy drive to restaurants, beaches, and the marinas.

Poolside Tiny House
Wilbert and Christine were wonderful hosts who took very good care of us! They drove us to the supermarket and to the rental car place and always made sure we had what we needed. The best hosts I've ever had on airbnb!

Beautiful Studio SMALL CAR Inclusive
Great stay! The location was very central, quiet, and safe. Danielle provided us with many great recommendations and was extremely responsive throughout our entire stay. You definitely need a car to fully enjoy the island so it was amazing have one included with the stay, as well as the beach chairs and umbrella. We felt safe the entire time and the location is very quiet and peaceful. We would stay again!

Spacious Studio Villa - Excellent Value for Money
Keno is very responsive and gave clear instructions. I would come back again

Beautiful Sunset Villa with Infiniti Pool
My wife and I really enjoyed our stay at Beautiful Sunset. We had so much fun with the private pool and scenery from the pool and patio area. I would definitely book again!

Hidden Gem features a lovely 1 Bedroom Studio
Well this place is absolutely amazing cute you have everything you need for your Vacation Claudia and Floyd are super nice and Claudia makes you feel that just like home if we go back to Turks were definitely going back here if it's Available thanks again Claudia Mark&Lise
Apartment rentals with outdoor seating

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!!

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 🌞
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!

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.

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!

Amazing Grace Bay Views, Terraces Pools & Location
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.

Paradise Nest Penthouse-Million Dollar Ocean Views
From the time of booking to check out Janus was extremely responsive and provided great communication. The condo was a perfect fit for our family of 5. The patio view was amazing to enjoy our early morning coffee or late afternoon drinks before dinner. The trade winds during the stay on the patio were nice. The condo description and photos depicted on airbnd is what we saw on arrival. We appreciated that beach chairs and a cooler were provided for use during the trip. We were fortunate to arrive on a Tuesday and we ended up arriving early. Janus, was accommodating with early check in.
Quick stats about holiday rentals with outdoor seating in Leeward Settlement
Total rentals
170 properties
Nightly prices starting at
₹12,116 before taxes and fees
Total number of reviews
4.3K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
150 properties have a pool
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