Leeward Settlement Holiday Rentals from AU$380: Search Short-Term Rentals

Q: 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 30% Off Thanksgiving - Private Pool, Walk to Beach! .

Check Leeward Settlement holiday rental availability

Holiday Rentals in Leeward Settlement

Outdoor pool, pool umbrellas, pool loungers

"The layout of the property was ideal. The amenities were within close proximity and well maintained. The parking facilities were also great. Overall, I would definitely recommend and return if possible. My experience at the front desk was also warm and welcoming. However, my only gripe somewhat is, the stairs leading up to the reception is difficult with heavy bags. I would recommend a ramp that would help reduce the strain on customers, and would also be conscious of persons with different...

"Very quiet and clean "

On the beach, sun-loungers, beach towels

"Property was perfect. Ben was amazing and super friendly. Loved the comfortable beds. The view is stunning. The water toys are perfect. "

"My family and I stayed for seven days at this beautiful home. The host was very accommodating and had great communication. We had wide range of needs as we had a one year old toddler to a 80-year-old grandmother. The home is at advertise we had an overall great day. Location was near site we wanted to visit. And the neighborhood felt safe."

Beach nearby, white sand, sun-loungers, beach umbrellas

"This is our second consecutive year visiting the TCI and staying at the Inn at Grace Bay. Ariel and Jane, the property managers are not only amazing humans but also incredibly good at their jobs, making you feel welcome and supported. Within walking distance we had access to shopping, restaurants, bars, a gourmet supermarket, beautiful Grace Bay beach, spas, Potcake Place, and The Bight where we enjoyed the Fish Fry festivities. You won't regret it. "

"We had a wonderful stay. It was our third visit to the island, but our first time staying at The Somerset. We will be back! The staff is warm, friendly and caring. The grounds are beautiful and clean. Foster and Winston in particular made this stay very special. They went above and beyond with their kindness and helped me figure out some travel issues I encountered with success. "

includes taxes & fees

7 Dec - 8 Dec

"The best location near the most beautiful beach we’ve ever seen!! "

includes taxes & fees

1 Dec - 2 Dec

"It is a lovely property that offers a vacation-style experience. However, no staff is available after 7 p.m."

includes taxes & fees

20 Dec - 21 Dec

"Grace Bay Beach Ocean Villas needs to be on your target list of exceptional facilities if you want a romantic spot for vacationing. The Villas have everything you want/need and the grounds are pristine and relaxing. A paved walkway to your private beach from which you can walk 20 minutes west to Smiths Reef or 40 Minutes east to the Bite – both great snorkeling. Have meals in your Villa (Great IGA a short drive away)or dine on Conch at the Shark Bite and other restaurants only a 7 minute walk...

includes taxes & fees

5 Dec - 6 Dec

"Good place Car required "

"Loved the location!!!! We love this Hidden Gem resort. It was nice being able to walk everywhere and not need to get a taxi for most things we did. Staff was extremely nice & helpful with helping us make the most of our trip. Property could use a little updating and nicer bedding, but we loved this little place & highly recommend it to others! Hope to be back someday soon. "

"This is a long story, but due to delays, we missed our flight to Grand Turk. We scrambled to find a place to stay, but located this villa allowing a one night booking. I found this villa on Expedia and it was just what we needed. The host and owner was very nice. The favorite part of our stay was the hospitality of the host. We had everything we needed!"

includes taxes & fees

8 Dec - 9 Dec

"It wasn't too far away from everything, but was far enough that it felt like you weren't in the middle of all the touristy spots. "

Family Villa, 2 Bedrooms, Ocean View, Beachfront | Beach

"The place is beautiful it’s clean and has everything you need and having the beach in your backyard is so relaxing sitting out while the sun rises "

"It was a lovely experience , we will be back someday"

"Most clean beach & water"

"This is a pretty place. Easy to get away. The room was very nice and the common area around the small pool was pretty (get your mosquito spray out). Luckily, I found the place on my own. 2 taxi drivers were lost trying to get there. As well, I stumbled onto and into the room; I finally was able to call someone and 45 minutes later, a nice lady, Luz, showed up to say hi. Good that I was in the correct room. But, it is away - it isn’t close to the downtown bustle of Grace Bay and the...

includes taxes & fees

3 Dec - 4 Dec

"The house was well equipped and comfortable with plenty of gathering space for our family. The deck, pool area and dock were all nice spaces with spectactular views. We enjoyed watching the sunrise and sipping coffee overlooking the sound. We had a maintenance issue with the pool, but property manager and maintence man addressed it immediately. We truly enjoyed our stay and are thankful to have made wonderful memories on Chalk Sound."

"2 Families shared this home for a week. Absolutely beautiful home, great location to the beach, plenty of space for everyone to spread out in the house. Communication with the Owner and Property Managers was quick and always helpful. We all enjoyed having the refreshing pool to jump in whenever we wanted. Highly recommend this home and location. "

2-Bedroom Oceanfront (2212) | Beach/ocean view

"My family of 4 stayed at Coral Gardens for in early June 2024. We loved the location and the amount of space. We loved all of the room and the amazing ocean view we had at Coral Gardens! Coral Gardens was very clean, the A/C worked well, and the staff were friendly and helpful. There were plenty of chairs with umbrellas on the beach and fresh towels were provided at the desk by the beach. Snorkeling by the resort is amazing! It was nice not having to drive or take a boat anywhere else to...

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Other types of properties in Leeward Settlement you may be interested in

"Everyone is so friendly, and the food is fantastic. The property is clean and well tended. "

includes taxes & fees

25 Nov - 26 Nov

"The layout of the property was ideal. The amenities were within close proximity and well maintained. The parking facilities were also great. Overall, I would definitely recommend and return if possible. My experience at the front desk was also warm and welcoming. However, my only gripe somewhat is, the stairs leading up to the reception is difficult with heavy bags. I would recommend a ramp that would help reduce the strain on customers, and would also be conscious of persons with different...

"We loved our time at Villa Kendara and plan to return to Turks & Caicos. Thanks for sharing your home with us."

Find out more about Leeward Settlement

Everything you need to know about Leeward Settlement holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Leeward Settlement holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leeward Settlement holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Leeward Settlement holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leeward Settlement. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Leeward Settlement holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Leeward Settlement holiday rentals we have selected for you start as low as AU$380 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Leeward Settlement rentals

At Expedia, we put the best Leeward Settlement holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Leeward Settlement rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leeward Settlement holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leeward Settlement. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Leeward Settlement Holiday Home Travel Info

Number of holiday homes	160
Popular accommodation	Leeward Settlement villas
Known landmarks	Grace Bay Beach, Providenciales Beaches and Turtle Cove
International airport	Providenciales (PLS-Providenciales Intl.)

Recent reviews of Leeward Settlement properties

Villa Kendara~BK 1/25-2/1 & 4/5 ON~Private~Gated~SeaFront Guest~Panorama View

5/5 Excellent

Beautiful Retreat

"We loved our time at Villa Kendara and plan to return to Turks & Caicos. Thanks for sharing your home with us."

A verified traveller stayed at Villa Kendara~BK 1/25-2/1 & 4/5 ON~Private~Gated~SeaFront Guest~Panorama View

Posted 3 days ago

5/5 Excellent

"The in room coffee was terrible! (lol) We used the shuttle daily, it it would be good to have a shuttle that traveled further west and to the grocery store. The staff was lovely and helpful! We felt very safe! Our room was clean and well maintained. The lobby needs updating. The landscaping needed attention. Overall, those were small details that would improve a nice place. The location isn’t great for active young people, but it is great for families and those not interested in night life and partying! "

A verified traveller stayed at Ocean Club Resort

Posted 4 days ago

5/5 Excellent

"Highly recommended. Recently stayed here for four nights on our first visit to Turks and Caicos. Paid extra for ocean view room, which was well worth it. Rooms are actually condos, so it doesn’t have that hotel feel; instead, it’s smaller, less crowded, less impersonal. Staff mainly very friendly and helpful. Excellent stretch of beach, small but nice pool, plenty of cabanas and loungers to go around, and free non-motorized water sports ($5 per day for snorkeling gear), which is a BIG plus; I went out on the Hobie Cat four times. If you don’t know how to sail, crew will take you. Only downside is that food and beverages are eye-wateringly expensive (same as everywhere in T&C). Best to avoid eating or drinking here (particularly on the beach; nearly $100 for two cocktails and two appetizers!!), which is why we bought supplies at nearby Graceway IGA supermarket. Will stay here again if we come back - preferred over big chain hotels further up the beach."

A verified traveller stayed at Windsong on the Reef

Posted 7 days ago

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 30% Off Thanksgiving - Private Pool, Walk to Beach!.

How many holiday rentals will I find in Leeward Settlement?

With 48 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.

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Leeward Settlement Holiday Rentals

Check Leeward Settlement holiday rental availability

Holiday Rentals in Leeward Settlement

The Atrium Resort

The Atrium Resort

Checkers Vacation Homes

Checkers Vacation Homes

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

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

Villa Tropica - Near Grace Bay Beach - Newly Remodelled

Villa Tropica - Near Grace Bay Beach - Newly Remodelled

Inn at Grace Bay

Inn at Grace Bay

The Somerset on Grace Bay

The Somerset on Grace Bay

South Fleetwood Grace Bay

South Fleetwood Grace Bay

H2O LifeStyle Resort

H2O LifeStyle Resort

Grace Bay Beach Ocean Villas

Grace Bay Beach Ocean Villas

Sea Grape Studios

Sea Grape Studios

Island Club Turks

Island Club Turks

Villa Serenity by the water

Villa Serenity by the water

Dream Villas Provo

Dream Villas Provo

Caribbean Sea Breeze Villas

Caribbean Sea Breeze Villas

Harbour Club Villas & Marina

Harbour Club Villas & Marina

The Tuscany on Grace Bay

The Tuscany on Grace Bay

Grace Bay Beach Ocean Villas, Bougainvillea Villa. Rated #1 On Trip Advisor.

Grace Bay Beach Ocean Villas, Bougainvillea Villa. Rated #1 On Trip Advisor.

WOW! Waterfront Chalk Sound Oasis w/ Infinity Pool. Kayaks & Canoe

WOW! Waterfront Chalk Sound Oasis w/ Infinity Pool. Kayaks & Canoe

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

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

Coral Gardens on Grace Bay

Coral Gardens on Grace Bay

Other types of properties in Leeward Settlement you may be interested in

Blue Haven Resort - All Inclusive

Blue Haven Resort - All Inclusive

The Atrium Resort

The Atrium Resort

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

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

Black Friday: Members save 30%+

Find out more about Leeward Settlement

Find out more about Leeward Settlement

Leeward Settlement Holiday Home Travel Info

Recent reviews of Leeward Settlement properties

Recent reviews of Leeward Settlement properties

Villa Kendara~BK 1/25-2/1 & 4/5 ON~Private~Gated~SeaFront Guest~Panorama View

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions