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 $1,096 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.

Top Holiday Package Deals in Leeward Settlement

Price found within the past 48 hours. Click for updated prices.
Le Bleu Bed and Breakfast

Le Bleu Bed and Breakfast

3 out of 5
Price was CA $1,522, price is now CA $887 per person
CA $887
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Providenciales (PLS)
7.2/10 Good! (89 reviews)
The setting is pleasant, and the staff are very courteous. The only downside: I didn’t find a restaurant at the hotel.

Reviewed on Feb 6, 2026

Dream Villas Provo

Dream Villas Provo

4 out of 5
Price was CA $7,770, price is now CA $3,609 per person
CA $3,609
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Providenciales (PLS)
9/10 Wonderful! (53 reviews)
Clean and modern room. Equipped with full kitchen. Friendly staff.

Reviewed on Dec 21, 2025

The Park in Grace Bay

The Park in Grace Bay

4 out of 5
Grace Bay
Price was CA $5,664, price is now CA $3,274 per person
CA $3,274
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Providenciales (PLS)
No reviews
Kokomo Botanical Resort - Caribbean Family Cottages

Kokomo Botanical Resort - Caribbean Family Cottages

4 out of 5
The Bight
Price was CA $3,292, price is now CA $1,958 per person
CA $1,958
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Providenciales (PLS)
9/10 Wonderful! (294 reviews)
We booked this hotel because the rates were reasonable, the cottages had two bedrooms, and the location, while not on the beach, was central. The grounds are beautiful, the on-site restaurant was good and the staff were very accommodating. They have a shuttle to a beautiful and quiet beach on Grace Bay next to the Wymara where you can get a delicious lunch at their oceanfront restaurant. The shuttle runs on a regular schedule but the driver was always available to take us to and from the beach as needed. We had amazing massages at the spa. I only gave it four stars because the cottages are in need of updating - especially the bathrooms - but other than that we were happy with our decision to stay there. I definitely recommend renting a car - you will need it to explore the island and to get to off-site restaurants.

Reviewed on Jan 26, 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 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 $1,680 per night from Mar 9 to Mar 10
CA $1,680
CA $1,680 total
Mar 9 - Mar 10
includes taxes & fees
8.8/10 Excellent! (700 reviews)
The resort was so relaxed and the staff so friendly, I highly recommend it to anyone looking for a low key place to stay. And the ability to use their sister hotel on Grace Bay Beach gives you the best of both worlds!

Reviewed on Jan 31, 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! (210 reviews)
Pool is beautiful and well maintained. Location was convenient to everything we wanted to do and beach was an easy 5 minute walk

Reviewed on Dec 29, 2025

Get rates
The Atrium Resort
Beach Enclave

Beach Enclave

5 out of 5
47 Joe Wood Drive Providenciales
10/10 Exceptional! (3 reviews)
Our recent stay at Beach Enclave North Shore was absolutely unforgettable. From the moment we arrived, we were captivated by the breathtaking beauty of the surroundings. The villa itself was stunning – spacious, luxurious, and impeccably maintained. The private pool and beach was a highlight, offering ...

Reviewed on Apr 10, 2025

Get rates
Beach Enclave
See all 1,727 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 $887 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

4/5(19 reviews)

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

Leeward Beach

Provo Conch Farm

5/5(2 reviews)

You can learn about the history of Providenciales with a visit to Provo Conch Farm. Stroll along the seaside or discover the beautiful coral reefs in this romantic 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)
Half-Day Snorkeling & Conch Cruise with Beach Picnic

Half-Day Snorkeling Cruise

CA $201
per adult
94% of travellers recommend
Half-Day Snorkeling Cruise
4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

CA $199
per adult
98% of travellers recommend
4-Hour Catamaran Sail and Snorkel Tour from Grace Bay
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.