A beach with thatched umbrellas and a clear blue sea.

Leeward Settlement Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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.

The Latest Leeward Settlement Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 17 - Jan 21

    Dream Villas Provo + Flight

    Blue Hills
    4 nights
    3.5 star property
    9.4/10 - Exceptional (82 reviews)
    Roundtrip • Ottawa (YOW) - Providenciales (PLS)
    YOW - PLS • Nonstop PLS - YOW • Nonstop
    Save 100% on your flight
    CA $4,550
    CA $2,561
    per traveller
    found 1 day ago
    Dream Villas Provo
  • Jan 16 - Jan 22

    Long Bay Beach Club + Flight

    Long Bay Hills
    6 nights
    5.0 star property
    10/10 - Exceptional (4 reviews)
    "."
    Reviewed August 3, 2026
    Roundtrip • Ottawa (YOW) - Providenciales (PLS)
    YOW - PLS • 1 stop PLS - YOW • 1 stop
    CA $25,543
    CA $13,138
    per traveller
    found 1 day ago
    Long Bay Beach Club
  • Jan 16 - Jan 22

    Rooftop Villa Collection + Flight

    Grace Bay
    6 nights
    5.0 star property
    Roundtrip • Ottawa (YOW) - Providenciales (PLS)
    YOW - PLS • 1 stop PLS - YOW • 1 stop
    Save 100% on your flight
    CA $22,030
    CA $13,234
    per traveller
    found 1 day ago
    Rooftop Villa Collection
  • Jan 17 - Jan 21

    Bungalows at Windsong on the Reef + Flight

    Grace Bay
    4 nights
    4.0 star property
    9.0/10 - Wonderful (101 reviews)
    "We had an AMAZING stay. The property is well maintained. Amenities convenient. Food GOOD. Staff EXCEPTIONAL! Shout Out to Raheem!"
    Reviewed August 6, 2026
    Roundtrip • Ottawa (YOW) - Providenciales (PLS)
    YOW - PLS • Nonstop PLS - YOW • Nonstop
    Save 100% on your flight
    CA $6,238
    CA $3,852
    per traveller
    found 1 day ago
    Bungalows at Windsong on the Reef
  • Jan 17 - Jan 21

    Beachfront at Windsong on the Reef + Flight

    Grace Bay
    4 nights
    5.0 star property
    9.4/10 - Exceptional (224 reviews)
    Roundtrip • Ottawa (YOW) - Providenciales (PLS)
    YOW - PLS • Nonstop PLS - YOW • Nonstop
    Save 100% on your flight
    CA $4,611
    CA $2,889
    per traveller
    found 1 day ago
    Beachfront at Windsong on the Reef

Where to stay in Leeward Settlement

Find the best Leeward Settlement areas and neighborhoods for the activities you enjoy most.

Grace Bay

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.

The Bight

Travelers to The Bight praise its stunning beaches. If you've got some more time to explore, be sure to make a stop by Grace Bay Beach and Turtle Cove Marina.

Long Bay Hills

While visiting Long Bay Hills, you might make a stop by sights like Long Bay Beach and Providenciales Beaches.

Turtle Cove

If you're spending some time in Turtle Cove, Turtle Cove Marina and Providenciales Beaches are top sights worth seeing.

Venetian Road Settlement

While visiting Venetian Road Settlement, you might make a stop by sights like Providenciales Beaches and Turtle Tail.

Discover the most popular places to visit in Leeward Settlement

Leeward Settlement Hotel Deals

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?

Offering great value package deals from CA $2,561 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.

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