Leeward Settlement Vacations

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Find the Best Leeward Settlement Vacation Packages

Leeward Settlement Hotel Deals

Blue Haven Resort - All Inclusive
Blue Haven Resort - All Inclusive
4.5 out of 5
Leeward Marina, Providenciales, Providenciales
8.8/10 Excellent! (655 reviews)
"It’s a quiet peaceful resort. Great service and nice accommodations."

Reviewed on 27 March 2025

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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! (192 reviews)
"This is our 2nd time at the Atrium. It's very quiet, peaceful and beautiful. Our room this time had a couple of issues which is why we are giving it 4 stars instead of 5. Air conditioning wasn't working properly and the washing machine had some issues. All in all, we love the Atrium."

Reviewed on 25 February 2025

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The Atrium Resort
Villa Kendara~BOOK JUNE ON~Private~Gated~SeaFront GuestHouse~Panoramic View
Villa Kendara~BOOK JUNE ON~Private~Gated~SeaFront GuestHouse~Panoramic View
Long Bay
9.8/10 Exceptional! (91 reviews)
Ideal Getaway
"Carol and Tom’s little piece of paradise is fabulous. Villa Kendra provides a quiet, peaceful, private space to relax while also offering easy access to all the beaches and adventurous excursions. As the pictures suggest, the views of the beautiful turquoise waters are outstanding from the pool and ..."

Reviewed on 2 April 2025

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Villa Kendara~BOOK JUNE ON~Private~Gated~SeaFront GuestHouse~Panoramic View
See all 1,541 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 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.

Discover the most popular places to visit in Leeward Settlement

Turtle Cove showing general coastal views and a bay or harbor

Turtle Cove Marina

4.5/5(342 reviews)

Explore the waterfront in Providenciales with a trip to Turtle Cove Marina. Stroll along the seaside in this romantic area, or check out its top-notch restaurants.

Turtle Cove Marina
Pelican Beach

Pelican Beach

4.5/5(84 reviews)

Why not spend a carefree afternoon at Pelican Beach during your travels in Turtle Cove? Discover the coral reefs while you're in the area.

Pelican Beach
Chalk Sound

Chalk Sound

4.5/5(179 reviews)

Explore the great outdoors at Chalk Sound, a lovely green space in Providenciales. Stroll along the seaside in this romantic area, or seek out the snorkeling spots.

Chalk Sound