Leeward Settlement Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 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 Holiday

From its highlights to its hidden treasures, this city is best explored with a Leeward Settlement holiday package. Find a place to stay in Grace Bay Hills, which is good for golfing, walking and dining. Make your trip to Leeward Settlement even more fun by going sightseeing. Grace Bay Beach, Turtle Cove and Providenciales Beaches are some of the big attractions you'll want to explore. Check out Expedia's wide range of travel options and begin planning your ideal holiday to Leeward Settlement now.

Our guide on 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

Seated on a towel on clean white sand, you’ll be able to see world-class resorts, relaxing spa houses and snorkelers exploring the coral reef, all around one picturesque beach.

Find hotels in Grace Bay

Our pick of the best 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 AU$2,186 per night from 10 June to 11 June
AU$2,186
10 June - 11 June
includes taxes & fees
9/10 Wonderful! (743 reviews)
T Ange, Winchell were absolutely great, friendly and helpful. Overall lovely property but only thing I’d change is the menu option limitations however the food available was delicious..

Reviewed on 9 May 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 10 Apr 2026

Get rates
The Atrium Resort
Checkers Vacation Homes

Checkers Vacation Homes

3 out of 5
63 Grace Bay Road Providenciales Providenciales
7.6/10 Good! (56 reviews)
ok place for the price only complain no direct access to beach as the ad describes. headache to check in

Reviewed on 9 Apr 2026

Get rates
Checkers Vacation Homes
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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Leeward Settlement holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. However, how much your holiday to Leeward Settlement costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Leeward Settlement?
Travel in the low or shoulder season and you're likely to find cheap Leeward Settlement holiday packages. Keep in mind that school holiday periods and local events and festivals can impact prices, so do a little research before booking.
How many days is enough for Leeward Settlement?
The ideal length for your Leeward Settlement holiday depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to go to all the top sights and discover some hidden spots along the way.
How to find the best Leeward Settlement package deals?
Use Expedia's filter tool to help you find some of the best Leeward Settlement package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Leeward Settlement package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Leeward Settlement holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and stays individually. Better still, you can customise your Leeward Settlement getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Leeward Settlement?
Enjoy fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Leeward Settlement holiday.
How to plan a trip to Leeward Settlement?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Leeward Settlement.
  2. Set a budget: Factor in expenses such as food, flights and transportation when working out how much to save for your trip to Leeward Settlement. Then, pick a hotel that matches your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Decide how long to go for: Now that you're up to speed on Leeward Settlement, you can figure out the ideal length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Combine your airfare and accommodation: After you've settled on your travel dates and duration, book the ideal Leeward Settlement holiday package for you.

Activities

Half-Day Snorkeling & Conch Cruise with Beach Picnic

Half-Day Snorkeling Cruise

AU$226
per adult
94% of travellers recommend
Half-Day Snorkeling Cruise
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales

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

AU$169
per adult
96% of travellers recommend
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)
Airport Fast Track Arrival Service - SkyPass Caribbean

Airport Fast Track Arrival Service - SkyPass Caribbean

AU$106
per adult
100% of travellers recommend
Airport Fast Track Arrival Service - SkyPass Caribbean
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.