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
Blue Hills
CA $4,569
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Providenciales (PLS)
9.4/10 Exceptional! (81 reviews)
We had an incredible experience from booking to checkout! The Villas are located in an area that allows you privacy, but the convenience of still being close to dining, and other necessities. The check in and check out process were super simple, and they even made slight accommodations to help us when we had a flight delay. The villa has everything you might need in the kitchen if you choose to prepare meals there. We especially enjoyed the ability to walk steps off our sidewalk onto a beautiful beach, with included loungers, and water activity toys. Host response was always prompt, and again, accommodating to our changing needs. We wouldn’t hesitate to book this location again if we return to T&C.
Reviewed on Sep 24, 2026
Point Grace
Grace Bay
CA $5,399
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Providenciales (PLS)
9.6/10 Exceptional! (344 reviews)
The minute we arrived, we were greeted. All the staff were super friendly. Everything was super clean and really close to everything downtown!
Reviewed on Sep 24, 2026
Ambergris Cay Private Island - All-Inclusive
CA $12,884
per person
Dec 17 - Dec 24
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Providenciales (PLS)
9.8/10 Exceptional! (30 reviews)
Excellent place, excellent staff and beautiful private island. I cannot say a single bad thing about this place. We are planning to go back here every year. Thank you Ambergris Cay!
Reviewed on Sep 28, 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
4 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.
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
1 out of top 10 points of interest in this area
While visiting Long Bay Hills, you might make a stop by sights like Long Bay Beach and Providenciales Beaches.
Turtle Cove
2 out of top 10 points of interest in this area
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.
Leeward Settlement Hotel Deals
Blue Haven Resort - All-Inclusive
Leeward Marina Providenciales Providenciales
CA $1,279
CA $1,279 total
Nov 8 - Nov 9
includes taxes & fees
The Atrium Resort
Governor's Road Providenciales Providenciales
8.2/10 Very good! (220 reviews)
"Although this property is beautiful, we were fooled into thinking our room had a view like shown on their reservation site. We had a view of the elevator. It was a ghost town, no snack bar, no drink bar, no room service and a tricky AC unit that wouldn’t function on cold for long. I would suggest ..."
Reviewed on Aug 9, 2026
Barefoot Luxury – Silver Palms Cottage # 1, Beachfront with Pool on Long Bay
providenciales Caicos Islands
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 $3,117 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?
- 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.
- 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.
- 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.
- 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.
Stay near popular Leeward Settlement attractions
Photo by Staci Partlo
Leeward Beach
9.2/10 (962 reviews)
Why not spend a carefree afternoon at Leeward Beach during your travels in Providenciales? Amble around this relaxing area's seaside, or seek out the snorkeling spots.
Pelican Beach
9.2/10 (667 reviews)
Why not spend a carefree afternoon at Pelican Beach during your travels in Providenciales? Amble around this relaxing area's seaside and enjoy its top-notch restaurants.
Things to do
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)
CA $170
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.