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.
Bungalows at Windsong on the Reef

Bungalows at Windsong on the Reef

4 out of 5
Grace Bay
Price was CA $5,550, price is now CA $2,470 per person
CA $2,470
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Providenciales (PLS)
9/10 Wonderful! (75 reviews)
The majority of the staff was very friendly. The restaurant on- site has a limited menu and your experience will depend on who your server is. Some were not happy people. This resort needs an activity night every night or some fun things to do l, especially with kids. The rooms were beautiful, clean and the washer / dryer was a plus! Very nice resort but food and activity choices need some improvements.

Reviewed on Aug. 2, 2025

Long Bay Beach Club

Long Bay Beach Club

5 out of 5
Long Bay
Price was CA $16,498, price is now CA $7,300 per person
CA $7,300
per person
Oct 31 - Nov 5
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Providenciales (PLS)
10/10 Exceptional! (3 reviews)
Villa private Pool Long bay Hill

Villa private Pool Long bay Hill

2 out of 5
Long Bay
Price was CA $8,349, price is now CA $3,875 per person
CA $3,875
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Providenciales (PLS)
No reviews
Dream Villas Provo

Dream Villas Provo

4 out of 5
Price was CA $5,109, price is now CA $2,609 per person
CA $2,609
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Providenciales (PLS)
9/10 Wonderful! (45 reviews)
Jono the property manager made our stay peaceful! Amazing place with a. Great view, would come back again

Reviewed on Jul. 29, 2025

Point Grace

Point Grace

4.5 out of 5
Grace Bay
Price was CA $9,399, price is now CA $5,027 per person
CA $5,027
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Providenciales (PLS)
9.6/10 Exceptional! (286 reviews)
The staff was absolutely amazing. Especially , Locresha and Jim. I appreciated the hospitality and accommodation!

Reviewed on Aug. 21, 2025

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 showing a house, a sandy beach and tropical scenes

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 $995 per night from Aug 28 to Aug 29
CA $995
CA $995 total
Aug 28 - Aug 29
includes taxes & fees
8.8/10 Excellent! (674 reviews)
"Very relaxing. Beautiful property"

Reviewed on Aug. 20, 2025

Blue Haven Resort - All Inclusive
The Atrium Resort

The Atrium Resort

3.5 out of 5
Governor's Road, Leeward, Providenciales, Providenciales
8.2/10 Very Good! (204 reviews)
"Really beautiful property. Everyone is really nice. Bed very comfy. Had everything we needed for the week. About a 10 minute a walk to Sunset beach. You do want to rent a car as it is in Leeward beach area. Short drive to Grace Bay. Pool area is super nice with jacuzzi."

Reviewed on Jul. 30, 2025

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The Atrium Resort
Barefoot Luxury – Silver Palms Cottage, Beachfront with Pool on Long Bay

Barefoot Luxury – Silver Palms Cottage, Beachfront with Pool on Long Bay

providenciales, Caicos Islands
9.8/10 Exceptional! (80 reviews)
"We had an amazing stay at this cottage! It’s just steps from the beach, and we loved spending our days paddle boarding and searching for sea shells. The cottage itself was beautiful and perfectly maintained. Ben was incredibly helpful and made our stay even better. Highly recommend!"

Reviewed on Aug. 15, 2025

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Barefoot Luxury – Silver Palms Cottage, Beachfront with Pool on Long Bay
See all 1,619 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Leeward Settlement vacation package cost?
Offering great value package deals from CA $2,470 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

Leeward Beach

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
Grace Bay Beach which includes a beach

Grace Bay Beach

Stretch out on fine white sands and marvel at the intense turquoise blue of the Caribbean waters on this pristine and photogenic stretch of shore.

Grace Bay Beach
Turtle Cove which includes a bay or harbour and general coastal views

Turtle Cove Marina

At this picturesque cove, stroll by the yacht-filled marina, enjoy fresh seafood from one of the local restaurants and take part in a range of exciting watersports.

Turtle Cove Marina

Things to do

Clear Kayak Drone Photoshoot

Clear Kayak Drone Photoshoot

CA $187
per adult
80% of travellers recommend
Clear Kayak Drone Photoshoot
Clear Kayak Tour in Turks & Caicos Islands

Clear Kayak Tour in Turks & Caicos Islands

CA $158
per adult
Clear Kayak Tour in Turks & Caicos Islands
3HR Emerald reef snorkeling, iguana island and shipwreck tour

3HR Emerald reef snorkeling, iguana island and shipwreck tour

CA $154
per adult
3HR Emerald reef snorkeling, iguana island and shipwreck tour
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.