Leeward Settlement Vacation Packages

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Your Leeward Settlement Vacation

Say farewell to planning hassles and hello to a Leeward Settlement vacation package. With your travel details organized before you leave, you can focus on discovering this city, starting with Grace Bay Hills, which is great for families, watersports and coastal beaches. If your trip to Leeward Settlement includes some sightseeing, drop by much-loved attractions like Grace Bay Beach, Turtle Cove and Providenciales Beaches. Whoever you're taking time off with and whatever your bank balance, your dream Leeward Settlement vacation is just clicks away with Expedia.

Top Holiday Package Deals in Leeward Settlement

Price found within the past 48 hours. Click for updated prices.
Dream Villas Provo

Dream Villas Provo

3.5 out of 5
Blue Hills
Price was CA $3,752, price is now CA $2,300 per person
CA $2,300
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Providenciales (PLS)
9.2/10 Wonderful! (63 reviews)
Beautiful beachfront stay! Clean, relaxing, and perfect for a peaceful getaway.

Reviewed on May 8, 2026

Long Bay Beach Club

Long Bay Beach Club

5 out of 5
Long Bay Hills
Price was CA $19,543, price is now CA $10,023 per person
CA $10,023
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Providenciales (PLS)
10/10 Exceptional! (3 reviews)
Beachfront at Windsong on the Reef

Beachfront at Windsong on the Reef

5 out of 5
Grace Bay
Price was CA $4,528, price is now CA $2,838 per person
CA $2,838
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Providenciales (PLS)
9.2/10 Wonderful! (135 reviews)
We had newer room in the building, it had a lovely kitchen and the view was spectacular Gym was good, grounds were well kept. For me I feel, food selection and meals could be better. Limited and pretty basic food , nothing wow about food, we ate elsewhere on many occasions. Other than that, beautiful beach and quiet location, a bit far from the small town though .

Reviewed on May 15, 2026

Ambergris Cay Private Island - All-Inclusive

Ambergris Cay Private Island - All-Inclusive

5 out of 5
Price was CA $15,443, price is now CA $9,924 per person
CA $9,924
per person
Jul 19 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Providenciales (PLS)
9.6/10 Exceptional! (23 reviews)
We had a very nice stay. Will definitely come back

Reviewed on Mar 20, 2026

Bungalows at Windsong on the Reef

Bungalows at Windsong on the Reef

4 out of 5
Grace Bay
Price was CA $3,828, price is now CA $2,465 per person
CA $2,465
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Providenciales (PLS)
9/10 Wonderful! (90 reviews)
A wonderful reservationist at WindSong upgraded us to a beachfront unit, and it was fantastic. The staff was so welcoming and accommodating. The units are very comfortable and easy to live in. The location, and all the amenities--the white sand beach, dining in the dunes, watersports, and sparkling clean pool, are all within a very short walk of the units. WindSong is a place to rest and relax but also a great spot to have fun, and that we did! We'll be back!

Reviewed on May 16, 2026

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.

Find hotels in Grace Bay

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 CA $1,763 per night from May 19 to May 20
CA $1,763
CA $1,763 total
May 19 - May 20
includes taxes & fees
9/10 Wonderful! (749 reviews)
Very peaceful and quiet resort. Food is amazing.

Reviewed on May 17, 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
Beach Enclave

Beach Enclave

5 out of 5
47 Joe Wood Drive Providenciales
8.8/10 Excellent! (8 reviews)
Beautiful property and beautiful location. Staff was incredible, restaurant was the best we had on the island, vibe is good, super private, very elevated. Rooms are smaller than appear on the pictures but still beautiful.

Reviewed on Apr 5, 2026

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Beach Enclave
See all 1,728 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.
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Frequently asked questions

How much does a Leeward Settlement vacation package cost?
Offering great value package deals from CA $2,300 on Expedia, you'll be thrilled with how little a vacation to Leeward Settlement costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Leeward Settlement?
To pick up cheap Leeward Settlement vacation packages, organize your trip outside of busy periods such as public holidays. You'll typically find better availability and lower prices for hotels and flights.
How many days is enough for Leeward Settlement?
Leeward Settlement vacations can be as short or long as you like, but to get a real feel for this place, we think 5 days is about right. In this timeframe, you can visit top sights like Providenciales Beaches and Leeward Beach along with lesser-known spots. Don't skip neighbourhoods such as Turtle Cove and Grace Bay West either. If you plan wisely, you can even allow for a day trip or two from Leeward Settlement too.
How to find the best Leeward Settlement package deals?
Bagging a cheap Leeward Settlement package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget range, add some filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Leeward Settlement package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
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 hotels and flights separately. Better still, you can personalize your Leeward Settlement getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Leeward Settlement?
If you have your Leeward Settlement travel dates finalized, book as early as you can to grab some outstanding deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Leeward Settlement?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred time of year and the type of activities on offer will also help you decide when to vacation in Leeward Settlement.
  2. Set a budget: Consider costs such as flights, food and transportation when calculating how much to put aside for your trip to Leeward Settlement. Then, pick a property that matches your budget, whether that's a wallet-friendly stay or a swankier retreat.
  3. Decide your trip length: Consider how long you want to spend discovering Leeward Settlement. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customized Leeward Settlement vacation package.

Discover the most popular places to visit in Leeward Settlement

Beach vacation paradise woman tourist walking alone on remote island in the tuamotu islands, French Polynesia. Luxury travel destination. Panoramic banner.

Leeward Beach

Why not spend a carefree afternoon at Leeward Beach during your travels in Grace Bay? Amble around this relaxing area's seaside, or seek out the snorkeling spots.

Leeward Beach

Provo Conch Farm

You can learn about the history of Providenciales with a visit to Provo Conch Farm. Stroll along the beautiful beaches or discover the beautiful coral reefs in this family-friendly area.

Provo Conch Farm

Things to do

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales

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

CA $166
per adult
96% of travellers recommend
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)
Mangrove Clear Kayak Tour

Mangrove Clear Kayak Tour

CA $171
per adult
86% of travellers recommend
Mangrove Clear Kayak Tour
Half-Day Snorkeling & Conch Cruise with Beach Picnic

Half-Day Snorkeling Cruise

CA $222
per adult
94% of travellers recommend
Half-Day Snorkeling Cruise
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.