Leeward Settlement Vacations

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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

Grace Bay

3 out of top 10 points of interest in this area

This picturesque stretch of white sand and warm, turquoise water is home to luxury resorts, restaurants and one of the world’s largest barrier reefs.

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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 ₩1,901,450 per night from May 5 to May 6
₩1,901,450
₩1,901,450 total
May 5 - May 6
includes taxes & fees
9/10 Wonderful! (727 reviews)
Bar and staff were phenomenal, rooms can use an upgrade but definitely not horrible. It’s just hard to track what activities and restaurants are open since we get a paper print out of the info and mine went swimming day one. I’ll definitely be back!

Reviewed on Apr 10, 2026

Blue Haven Resort - All-Inclusive
The Atrium Resort

The Atrium Resort

3.5 out of 5
Governor's Road Providenciales Providenciales
8.2/10 Very Good! (214 reviews)
Clean condo, nice pool. Missing daily maintenance and providing necessities.

Reviewed on Apr 10, 2026

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The Atrium Resort
Checkers Vacation Homes

Checkers Vacation Homes

3 out of 5
63 Grace Bay Road Providenciales Providenciales
7.6/10 Good! (56 reviews)
ok place for the price only complain no direct access to beach as the ad describes. headache to check in

Reviewed on Apr 9, 2026

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Checkers Vacation Homes
See all 1,711 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.

Frequently asked questions

How much does a Leeward Settlement vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. However, how much your vacation 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 vacation packages. Keep in mind that school vacation 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 vacation 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 vacation package as soon as possible.
Is it cheaper to book a Leeward Settlement vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and stays individually. Better still, you can customize 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 vacation 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 vacation.
How to plan a trip to Leeward Settlement?

  1. Choose the ideal time to travel: Your schedule, favorite 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 accommodations: After you've settled on your travel dates and duration, book the ideal Leeward Settlement vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.