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Leeward Settlement Holiday Rentals

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Holiday Rentals in Leeward Settlement

The Atrium Resort

3.5 star property
8.2 out of 10, Very good, (190)
"Super modern & beautiful property. Loved the kitchen and the jacuzzi, certainly my two favorites things. "
The Atrium Resort

Beach Enclave

5.0 star property
10.0 out of 10, Exceptional, (2)
"Beach Enclave was stunning. Satheesh our butler was amazing and went over the top to make our stay great. If you are looking for quiet and calm shallow water I’d stay in long bay. If you want deeper water with waves I’d stay on the grace bay side."
Beach Enclave

Checkers Vacation Homes

3.0 star property
7.0 out of 10, Good, (32)
"Very quiet and clean "
Checkers Vacation Homes

Villa Tropica - Near Grace Bay Beach - Newly Remodelled

9.8 out of 10, Exceptional, (120)
"Overall stay was great. Very Clean and Open and bright.Quiet area which was perfect for our family. I highly recommend walking (very short walk) to sunset beach..2 blocks. Very safe area!"
Villa Tropica - Near Grace Bay Beach - Newly Remodelled

Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2

9.8 out of 10, Exceptional, (153)
"We rented both houses on the property to celebrate our anniversary with our family and friends. Everything was perfect. Kitchen had everything we needed to cook and prepare meals. We could easily walk to the shore club hotel on long bay beach for bars and restaurants. The kiting was fabulous we launched right from the private beach . . And there was lots to keep our non kiting friends entertained .. stand up paddle, kayaks , swimming pool, comfy bed in shade etc.our hosts were very responsive...
Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2

Newly Renovated Suite just 2 mins away from Grace Bay Beach with Beach Chairs

9.8 out of 10, Exceptional, (6)
"We stayed a week in Grace Bay and my experience was exceptional! The host made a point to get in touch with me days before my scheduled arrival and the property manager greeted us on site for a tour. Clean showers, rooms, kitchen, functioning Wi-Fi, AC, etc, all of the accommodations were on point. What made our experience perfect was the property manager. I have NEVER had a host as attentive as Dean! He was available at all hours by phone to give us recommendations on restaurants, taxis, and...
Newly Renovated Suite just 2 mins away from Grace Bay Beach with Beach Chairs

Inn at Grace Bay

3.0 star property
9.4 out of 10, Exceptional, (566)
"The Inn was a great place to stay for our week in Turks. The Grace Bay Area has so many restaurants in walking distance and the grocery store was also walkable. The condo was clean and quiet. The pool area was tropical and quiet. It was an easy walk to the beach and it felt safe around the area. We only rented a car one day to explore the island. The rest of the time we walked. It was nice to have the excellent croissants at the poop each morning. The Inn manager was available daily and...
Inn at Grace Bay

Coral Gardens on Grace Bay

3.5 star property
8.8 out of 10, Excellent, (290)
"We visited in November 2024, the location is absolutely the best. Having the beach right at your doorstep can’t be beat. The staff are extremely friendly and helpful. "
The price is AU$1,677
includes taxes & fees
5 Mar - 6 Mar
Coral Gardens on Grace Bay

Northwest Point Resort

3.0 star property
8.4 out of 10, Very good, (139)
"Loved the remoteness and privacy. Walks on the beach were fantastic each day. Exploring the national park and reefs, so close to the property, were an added bonus ~ with turtles! We loved the location of the unit, view from our balcony and easy walk to the beach. The unit was very well stocked so made cooking very easy. "
The price is AU$1,008
includes taxes & fees
5 Mar - 6 Mar
Northwest Point Resort

The Somerset on Grace Bay

5.0 star property
9.6 out of 10, Exceptional, (164)
"A favorite spot we visit yearly. Beautiful property with excellent service."
The price is AU$2,412
includes taxes & fees
21 Mar - 22 Mar
The Somerset on Grace Bay

The Tuscany on Grace Bay

4.0 star property
10.0 out of 10, Exceptional, (178)
"I really do not know where to start. This was the most exciting and beautiful properties that my family and I have ever stayed in! To tell my whole experience would be a the page letter! All I can say is management and the house staff were amazing!!! It was like a home away from home! We were greeted with the friendliest people in the world! So needless to say... we will be back! If you want a lovely place to stay and relax.. please inquire!!! You won't regret it!"
The Tuscany on Grace Bay

South Fleetwood Grace Bay

3.0 star property
8.4 out of 10, Very good, (159)
"This was an absolute gorgeous Villa, we stayed in studio 2 and really enjoyed it. The beach is 2 min away and within 5 min you are downtown and have dining an shopping options. The studio offered beach chairs, and an umbrella. While you don’t need it for grave bay beach (they have beach chairs) we used them for the other beaches we went to. We would definitely rent this gem again. "
South Fleetwood Grace Bay

Harbour Club Villas & Marina

3.0 star property
10.0 out of 10, Exceptional, (29)
"The villas have everything you need and want for a relaxing and comfortable stay. It was nice to be away from the resort areas; a car is required. Walking distance to a local bar and grill. "
Harbour Club Villas & Marina

H2O LifeStyle Resort

4.0 star property
9.4 out of 10, Exceptional, (73)
"Amazing Hotel. Clean, friendly stuff and very accommodating. Julie the GM was very friendly and polite. Adrian was very informative and friendly. Love it!!!!"
The price is AU$1,294
includes taxes & fees
23 Feb - 24 Feb
H2O LifeStyle Resort

Sea Grape Studios

3.0 star property
8.8 out of 10, Excellent, (67)
"Clean private quiet "
Sea Grape Studios

The Venetian on Grace Bay

4.0 star property
9.8 out of 10, Exceptional, (72)
"Great place. Fabulous views. "
The Venetian on Grace Bay

Dream Villas Provo

4.5 star property
8.6 out of 10, Excellent, (23)
"Beautiful views, highly recommend! "
Dream Villas Provo

Palm Jewel - Luxury villa, private outdoor oasis w/pool, walk to SAPODILLA BEACH

10.0 out of 10, Exceptional, (86)
"Great house for families. Everything you need for a family with teens and young kids. Location perfect. Well stocked and very clean. We loved it"
Palm Jewel - Luxury villa, private outdoor oasis w/pool, walk to SAPODILLA BEACH

Oceanview Oasis w/ pool, gym, king bed, wifi, AC & walk to restaurants & beach

9.6 out of 10, Exceptional, (4)
"Great central location on island, clean, easy process."
The price is AU$390
includes taxes & fees
22 Mar - 23 Mar
Oceanview Oasis w/ pool, gym, king bed, wifi, AC & walk to restaurants & beach

Caribbean Sea Breeze Villas

3.0 star property
9.2 out of 10, Wonderful, (87)
"The property is just perfect for our stay, beach front, silent, near to everything what we need (restaurants, grocery stores). Even though the communication with the property is slow/late response, the housekeeper, Ms. Lita, explained everything to us, she even recommend where to shop and eat, she keep our place very clean, thank you!"
Caribbean Sea Breeze Villas
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Leeward Settlement you may be interested in

Blue Haven Resort - All Inclusive

4.0 star property
9.0 out of 10, Wonderful, (648)
"We spent our honeymoon at Blue Haven and were pleased. The staff was helpful and fun providing ideas on how to experience the island. Mikkaela (front desk) and Smiley (Acticites) were helpful and added to the experience. The onsite activities were a limited to a few water sports, and 2 or 3 daily afternoon 'games', but no group activities such as yoga, or fitness experiences. As for the room, there were a few items in the room that could use some updates, but overall a great stay and view....
Blue Haven Resort - All Inclusive

The Atrium Resort

3.5 star property
8.2 out of 10, Very good, (190)
"Super modern & beautiful property. Loved the kitchen and the jacuzzi, certainly my two favorites things. "
The Atrium Resort

Villa Kendara~BOOK APRIL 5th ON~Private~Gated~SeaFront GuestHouse~Panoramic View

10.0 out of 10, Exceptional, (168)
"Couldn’t imagine a better view on the island than the one from the pool. The above garage unit doesn’t have much of one, but it is well very appointed (kitchen, bath, desk, grill, etc.). Great for a couple. Could easily be a 5 with more comfortable couch, chairs and poolside lounges. We would go back!"
Villa Kendara~BOOK APRIL 5th ON~Private~Gated~SeaFront GuestHouse~Panoramic View
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a holiday rental in Leeward Settlement?

Yes, there are holiday rentals close to the most popular sights in Leeward Settlement, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Leeward Settlement has to offer?

Villa Serenity by the water: This holiday home rental outside Leeward Settlement is located in the historical district, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities such as a microwave and kitchenware can make your holiday run smoothly. Another good choice for your trip to Leeward Settlement is Romantic Getway Steps from the Beach.

How many holiday rentals will I find in Leeward Settlement?

With 51 Expedia holiday rentals, you're guaranteed to find just the right place for your Leeward Settlement stay.

What’s there to see and do in Leeward Settlement?

Grace Bay Beach and Leeward Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Long Bay Beach and Providenciales Beaches are other places worth a visit.

What’s a holiday rental in Leeward Settlement like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Leeward Settlement. Holiday rentals feature extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for family gatherings.