Leeward Settlement Holidays

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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
A beach with clear turquoise water, white sand, and a few footprints. There are houses and palm trees in the background.

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.

Find hotels in Grace Bay

Top hotels in Leeward Settlement

Blue Haven Resort - All-Inclusive

Blue Haven Resort - All-Inclusive

4.5 out of 5
Leeward Marina Providenciales Providenciales
9/10 Wonderful! (786 reviews)
"What an excellent resort!!! The staff are amazing (to mentione a few, Nathalie, Cadet, Pedro, Shameka, Yatiana or Tayiana were highlights of excellent staff) but I can’t give enough credit and thank you for all staff that made us feel welcome and at home. The resort is clean and in an area that offers ..."

Reviewed on 7 Jul, 2026

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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

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The Atrium Resort
Beach Enclave

Beach Enclave

5 out of 5
47 Joe Wood Drive Providenciales
7.8/10 Good! (10 reviews)
"Beach Enclave offers a private beachfront experience with only 5-6 rooms, creating a quiet atmosphere less than 10 minutes from Grace Bay. Guests should know there is no traditional front desk. Arrival must be coordinated in advance via email, and communication is handled primarily through WhatsApp ..."

Reviewed on 5 Jun, 2026

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Beach Enclave
See all 1,749 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.

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.

Stay near popular Leeward Settlement attractions

A beach with clear turquoise water, white sand, and palm trees under a bright blue sky.

Leeward Beach

9.2/10 (962 reviews)
Why not spend a care-free afternoon at Leeward Beach during your travels in Grace Bay? Amble around this relaxing area's seaside or seek out the snorkelling spots.
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Things to do

Half-Day Snorkeling & Conch Cruise with Beach Picnic

Half-Day Snorkeling Cruise

S$209
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)

S$157
per adult
96% of travellers recommend
2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales (Adult Only)
4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

S$188
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.