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Top Holiday Rentals in Leeward Settlement

The Atrium Resort
3.5 star property
8.2 out of 10, Very good, 152 reviews
"Great stay, peaceful not too far from the action but you’ll need your own transportation. "
The Atrium Resort
Checkers Vacation Homes
3.0 star property
7.0 out of 10, Good, 32 reviews
"Very quiet and clean "
Checkers Vacation Homes
Villa Tropica - Near Grace Bay Beach - Newly Remodeled
10.0 out of 10, Exceptional, 110 reviews
"Communication with property manager was excellent! The home was absolutely incredible. We had a group of five couples. The layout of the home fit our group perfectly. The pool area was amazing. House was stocked with essentials that lasted us the week. Need towel racks or hooks in the upstairs bathroom. No place to hang wet towels. Other than that, no complaints. Highly recommend this home!!"
Villa Tropica - Near Grace Bay Beach - Newly Remodeled
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Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2
9.8 out of 10, Exceptional, 138 reviews
"What an incredible place. Right on the beach in pretty much your own private cove, pictures don’t do justice as to how beautiful this is. We had some overcast days and some wind which was expected. Way awesome watching the kite surfers. The few days where it cleared up and the wind died down, not sure you can find anything better. Quiet, tranquil, absolutely stunning. Wesley and Tatum stopped by to welcome us, Ben was there if you needed anything and gladly did a couple of fires for us. The...
Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2
H2O LifeStyle Resort
4.0 star property
9.4 out of 10, Exceptional, 54 reviews
"This property is amazing and extremely quiet clean and beautiful I would definitely visit and stay here again"
The price is £471
includes taxes & fees
6 Jun - 7 Jun
H2O LifeStyle Resort
Inn at Grace Bay
3.0 star property
9.4 out of 10, Exceptional, 522 reviews
"We has the best time here. Ariel was amazing and I couldn’t say enough about how he hooked us up for all kinds of deals for day trips and jet skis. He seriously is very dedicated and passionate about the guests. The only issue we had was a water leak through the wall when we gad some torrential rain that should be looked at asap. Ariel was great and got the place cleaned up and the tv on the wall replaced asap. Thank you for a great stay!"
Inn at Grace Bay
Neptune Villas
3.5 star property
9.2 out of 10, Wonderful, 215 reviews
"The view of Chalk Sound is beautiful! Every meal we had at Las Brisas was delicious and we loved the beach at Sappdilla Bay."
The price is £295
includes taxes & fees
11 Jun - 12 Jun
Neptune Villas
The Tuscany on Grace Bay
4.0 star property
10.0 out of 10, Exceptional, 148 reviews
"Extremely convenient stay with all the luxuries we could want. We could hear and see the beach right in front of our balcony. We could walk to the pool and the beach with minimal steps. Some Pool and beach floaties are provided as well as beach towels. They give you a local phone to use if needed. The place was a condo but they also had housekeeping daily. During the day the restaurant next door does rounds and takes orders for food and drinks they will deliver to your chair. I would definitely...
The Tuscany on Grace Bay
Sea Grape Studios
3.0 star property
9.0 out of 10, Wonderful, 57 reviews
"The property was in close proximity to Grace Bay, dining, and also the airport."
Sea Grape Studios
The Venetian on Grace Bay
4.0 star property
9.8 out of 10, Exceptional, 63 reviews
"Liked that it was away from other busy hotels, which we intentionally wanted, but did require a 30 minute walk or a taxi ride at $6-$20 per person, depending on time of day/night to get to busier area with restaurants and casino. "
The Venetian on Grace Bay
South Fleetwood Grace Bay
3.0 star property
8.6 out of 10, Excellent, 137 reviews
"Great time at the South Fleetwood!! Good location, nice villa, nice pool. Kitchen if u wish to cook! Great neighbors too we all enjoyed our time."
South Fleetwood Grace Bay
The Somerset on Grace Bay
5.0 star property
9.4 out of 10, Exceptional, 151 reviews
"We stayed had a great vacation at The Somerset with our kids who are 12 and 14. It is a quiet resort, the grounds are very nice, the beach is beautiful and all of the staff we great! The condo we stayed in was very spacious and cleaned daily including turn down service each night. I would highly recommend staying here."
The price is £520
includes taxes & fees
16 Jun - 17 Jun
The Somerset on Grace Bay
Grace Bay Beach Ocean Villas
3.5 star property
8.8 out of 10, Excellent, 123 reviews
"I would have given 5 stars but office manager wasn’t always accessible. The water would also go in and out at random times so we didn’t have water for showers. I did like that the beach was private and it’s a one minute walk. It was very quiet and secluded in comparison to the resorts. Very clean as well and we had our own pool. Would still highly recommend it. Wish the AC was stronger in the room as well. "
The price is £293
includes taxes & fees
7 Jun - 8 Jun
Grace Bay Beach Ocean Villas
Island Club Turks
3.0 star property
9.4 out of 10, Exceptional, 114 reviews
"We enjoyed our stay. The staff was friendly. It’s a good walk to the beach but we loved how close restaurants and shops are. It was nice to have 2 rooms. "
Island Club Turks
Northwest Point Resort
3.0 star property
8.4 out of 10, Very good, 124 reviews
"I enjoyed it so much I stayed twice , the report is beautiful , remote , quiet , the beach is great for long walks and the on site restaurant was so convenient for lunch and dinner , Lisa the manager was very helpful and responded to help us with car rentals and day tripping , I highly recommend the resort , "
The price is £455
includes taxes & fees
7 Jun - 8 Jun
Northwest Point Resort
Harbour Club Villas & Marina
3.0 star property
10.0 out of 10, Exceptional, 21 reviews
"I absolutely loved this amazing quiet oasis. Marta and Mike were so friendly & accommodating. The villas were private, clean, & fully equipped with necessities to cook or eat out. Was able to have an in Villa massage by Phenomenal Mobile Massage. Close to the airport, activities, stores, & restaurants. Will be staying here again. "
Harbour Club Villas & Marina
Caribbean Sea Breeze Villas
3.0 star property
9.2 out of 10, Wonderful, 75 reviews
"The outlets needs to be fixed. "
Caribbean Sea Breeze Villas
Dream Villas Provo
2.5 star property
8.4 out of 10, Very good, 8 reviews
"We just got back from our stay at Dream Villas Provo! We loved it. We stayed in unit 3B and it was on the second floor with a roof top splash pool. The unit was cozy and perfect for two people! We spent most of our time in the splash pool! We saw turtles from our balcony and the horses go by a couple times a day! You need a car and it’s not located in the best neighborhood but we felt safe and had no safety concerns. Our host Charlene was great and she helped my husband with Roses for our...
Dream Villas Provo
La Vista Azul Modern Condo Ocean Views
3.5 star property
8.0 out of 10, Very good, 13 reviews
"Fantastic room! Excellent communications! No problems at all!!"
La Vista Azul Modern Condo Ocean Views
Coral Gardens on Grace Bay
3.5 star property
8.8 out of 10, Excellent, 284 reviews
"Private friendly and well located to reef and excursion pick up."
Coral Gardens on Grace Bay
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See all available properties in Leeward Settlement
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.

Leeward Settlement Holiday Rental Travel Info

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

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, 614 reviews
"I liked the property. I wish they'd make eating accommodations for guest arriving between 4-6pm. Also guest services personnel could use some training on being more helpful when asked questions they dont know how to answer. Other than that it was a good trip."
The price is £858
includes taxes & fees
7 Jun - 8 Jun
Blue Haven Resort - All Inclusive
The Atrium Resort
3.5 star property
8.2 out of 10, Very good, 152 reviews
"Great stay, peaceful not too far from the action but you’ll need your own transportation. "
The Atrium Resort
Villa Kendara~BK AUG/SEP DEAL~Private~Gated~SeaFront Guesthouse~Panoramic View
10.0 out of 10, Exceptional, 160 reviews
"Villa Kendara was the perfect peaceful private getaway with a gorgeous ocean view of Long Bay from the pool. The sunning deck by ocean was great with a convenient ladder to step into crystal clear, warm water and no more than chest deep for at least a half mile out. I know because I walked out to the floating tiki bar! Which was fun but drinks were pricey! Actually all food in TCI is pricey! Definitely bring food from home. The bay was perfect for floating and swimming. The villa was secluded...
Villa Kendara~BK AUG/SEP DEAL~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.

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, apart-hotels, 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 favorite 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 depends 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 £293 per night. Entering your travel dates in the search wizard you might find 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. 

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.

How many holiday rentals will I find in Leeward Settlement?

With 60 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?

Leeward Beach and Long Bay Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Grace 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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