Leeward Settlement Holidays

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Your Leeward Settlement Holiday

From its highlights to its hidden treasures, this city is best explored with a Leeward Settlement holiday package. Find a place to stay in Grace Bay Hills, which is good for golfing, walking and dining. Make your trip to Leeward Settlement even more fun by going sightseeing. Grace Bay Beach, Turtle Cove and Providenciales Beaches are some of the big attractions you'll want to explore. Check out Expedia's wide range of travel options and begin planning your ideal holiday to Leeward Settlement now.

Our guide on where to stay in Leeward Settlement

Find the best Leeward Settlement areas and neighborhoods for the activities you enjoy most. Learn more about Leeward Settlement
Grace Bay which includes a house, tropical scenes and a sandy beach

Grace Bay

3 out of top 10 points of interest in this area

Seated on a towel on clean white sand, you’ll be able to see world-class resorts, relaxing spa houses and snorkelers exploring the coral reef, all around one picturesque beach.

Find hotels in Grace Bay

Our pick of the best Leeward Settlement Hotel Deals

Blue Haven Resort - All-Inclusive

Blue Haven Resort - All-Inclusive

4.5 out of 5
Leeward Marina, Providenciales, Providenciales
The price is AU$1,140 per night from 8 Dec to 9 Dec
AU$1,140
8 Dec - 9 Dec
includes taxes & fees
8.8/10 Excellent! (680 reviews)
This is one of my wife and I’s favorite places to stay. It’s conveniently located across from the mangroves where we enjoy kayaking each day! The staff is very courteous and helpful, making it a must see resort!

Reviewed on 31 Oct 2025

Blue Haven Resort - All-Inclusive
The Atrium Resort

The Atrium Resort

3.5 out of 5
Governor's Road, Leeward, Providenciales, Providenciales
8/10 Very Good! (207 reviews)
Close to the beach

Reviewed on 30 Sept 2025

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The Atrium Resort
Checkers Vacation Homes

Checkers Vacation Homes

3 out of 5
63 Grace Bay Road, Providenciales, Providenciales
7/10 Good! (33 reviews)
I loved the homey feel, with the fully equipped kitchen and AC. Quiet place

Reviewed on 13 June 2025

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Checkers Vacation Homes
See all 1,674 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Leeward Settlement holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. However, how much your holiday to Leeward Settlement costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Leeward Settlement?
Travel in the low or shoulder season and you're likely to find cheap Leeward Settlement holiday packages. Keep in mind that school holiday periods and local events and festivals can impact prices, so do a little research before booking.
How many days is enough for Leeward Settlement?
The ideal length for your Leeward Settlement holiday depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to go to all the top sights and discover some hidden spots along the way.
How to find the best Leeward Settlement package deals?
Use Expedia's filter tool to help you find some of the best Leeward Settlement package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Leeward Settlement package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Leeward Settlement holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and stays individually. Better still, you can customise your Leeward Settlement getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Leeward Settlement?
Enjoy fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Leeward Settlement holiday.
How to plan a trip to Leeward Settlement?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Leeward Settlement.
  2. Set a budget: Factor in expenses such as food, flights and transportation when working out how much to save for your trip to Leeward Settlement. Then, pick a hotel that matches your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Decide how long to go for: Now that you're up to speed on Leeward Settlement, you can figure out the ideal length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Combine your airfare and accommodation: After you've settled on your travel dates and duration, book the ideal Leeward Settlement holiday package for you.

Discover the most popular places to visit in Leeward Settlement

Grace Bay Beach showing a sandy beach

Grace Bay Beach

Stretch out on fine white sands and marvel at the intense turquoise blue of the Caribbean waters on this pristine and photogenic stretch of shore.

Grace Bay Beach

The Regent Village

You can enjoy retail therapy at The Regent Village during your trip to Providenciales. Stroll along the beautiful beaches or discover the spectacular coral reefs in this relaxing area.

The Regent Village

Our Lady of Divine Providence Church

Our Lady of Divine Providence Church is just one of the places to see in Providenciales, so why not enjoy the other things to explore during your travels? Discover the spectacular coral reefs and top-notch restaurants in this romantic area.

Our Lady of Divine Providence Church

Activities

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)

AU$185
per adult
96% of travellers recommend
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)
Private Mangrove Cay Tours

Mangrove Cay Tour

AU$198
per adult
78% of travellers recommend
Mangrove Cay Tour
Clear Kayak Tour in Turks & Caicos Islands

Clear Kayak Tour in Turks & Caicos Islands

AU$175
per adult
Clear Kayak Tour in Turks & Caicos Islands
See all activities in Providenciales
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.