Leeward Settlement Holidays from £1,576

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Your Leeward Settlement Holiday

Say farewell to planning hassles and hello to a Leeward Settlement holiday package. With your travel details organised 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 holiday is just clicks away with Expedia.

Price found within the past 48 hours. Click for updated prices.
Dream Villas Provo

Dream Villas Provo

4 out of 5
Save 100% on your flight
per person
12 Oct - 18 Oct
found 1 day ago
Return flight included
London (LON) 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 29 Jul 2025

South Bank

South Bank

5 out of 5
Long Bay
Save 100% on your flight
per person
12 Oct - 18 Oct
found 1 day ago
Return flight included
London (LON) to Providenciales (PLS)
9.8/10 Exceptional! (9 reviews)
Wonderful experience.

Reviewed on 3 Jul 2025

Windsong on the Reef

Windsong on the Reef

4.5 out of 5
Grace Bay
Save 100% on your flight
per person
12 Oct - 18 Oct
found 1 day ago
Return flight included
London (LON) to Providenciales (PLS)
9.2/10 Wonderful! (1,000 reviews)
It’s a wonderful place to stay , very calm and fantastic beaches

Reviewed on 8 Aug 2025

Point Grace

Point Grace

4.5 out of 5
Grace Bay
Save 100% on your flight
per person
12 Oct - 18 Oct
found 1 day ago
Return flight included
London (LON) to Providenciales (PLS)
9.6/10 Exceptional! (282 reviews)
It was small and intimate. Sometimes the attitude at front desk was not kind at all.

Reviewed on 3 Aug 2025

Bungalows at Windsong on the Reef

Bungalows at Windsong on the Reef

4 out of 5
Grace Bay
Save 100% on your flight
per person
12 Oct - 18 Oct
found 1 day ago
Return flight included
London (LON) 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 2 Aug 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 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

Top hotels in Leeward Settlement

Blue Haven Resort - All Inclusive

Blue Haven Resort - All Inclusive

4.5 out of 5
Leeward Marina, Providenciales, Providenciales
The price is £535 per night from 31 Aug to 1 Sept
£535
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (672 reviews)
"It is a great place to relax and to enjoy nature."

Reviewed on 25 Jul 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 30 Jul 2025

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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 10 Apr 2025

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Beach Enclave
See all 1,622 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Leeward Settlement travel package cost?
Go from looking to booking with our Leeward Settlement travel packages, which start from a low £1,576. Choose the hotels and flights that suit your travel plans. Then, add on a few tours or experiences for an incredible adventure.
If I'm not able to travel, can I cancel my Leeward Settlement travel package?
You sure can, and we're here to help. You may be able to change or cancel your Leeward Settlement travel package for free if you booked in the last 24 hours. However, you may be charged a fee by your hotel, airline or car rental company if your booking is older than that. If your circumstances unexpectedly change, have a look at our Customer Service Portal for further information.
How do I get a cheap travel package to Leeward Settlement?
If you love landing a bargain, combine your bookings into a Leeward Settlement holiday package. Whether you're looking for flights, hotels, rental cars or activities, you can browse and book everything in one place. You'll have plenty of choice at your fingertips as well. Expedia has over 550 air carriers and 1,000,000 hotel options around the world to pick from. Fly with who you prefer, find a room where you like and save a bundle — now that's the perfect getaway!
Does Expedia offer Book Now, Pay Later Leeward Settlement holidays?
Your bank balance shouldn't prevent you from going on holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book an incredible getaway without hurting your hip pocket. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that suit all types of budgets, so you can take that well-deserved holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your holiday in multiple transactions.
  • Low deposit holidays: Hitting the "book now" button is much easier with this option. Just put down a small deposit on your escape and then start packing your suitcase.

Where should I stay in Leeward Settlement?
You'll want to stay where the action is. Many visitors book hotels around popular sights, such as Grace Bay Beach, The Regent Village Shopping Mall and Salt Mills Plaza.
What are the top hotels in Leeward Settlement?
If it's your very first time in Leeward Settlement, reserve a room at The Sands at Grace Bay or Windsong on the Reef. Both offer comfortable beds and are favourites with many travellers.
How far in advance should I book my Leeward Settlement holiday?
It can be tricky to know when the best time is to book your holiday to Leeward Settlement. But usually the earlier you book, the lower the prices. Sometimes, you can book your flights and hotels up to 12 months prior to departure. If you're considering a last-minute getaway, no need to stress! There are terrific deals posted on Expedia all the time.
What does an Expedia Leeward Settlement travel package include?
Expedia has everything you need to lock in Leeward Settlement getaway, but what goes into your package is your choice. Choose from any combination of hotels, rental cars and flights. Searching for some activities to keep you on the go? Once you've made your booking, you can add them on too. No matter your budget, there's a deal to meet your needs.
What should I know before booking a Leeward Settlement travel package?
You'll pick up impressive savings when you bundle your flights, hotels and rental cars into a package. Not only that, booking everything together makes trip planning much easier. So why waste money or time? Whether you're putting together a fancy romantic getaway or a low-cost family break, take a look at our package deals today.
Can I choose my airline with a Leeward Settlement Expedia travel package?
Yes, you're in charge. Expedia has access to more than 550 airlines worldwide, so you can tailor your Leeward Settlement getaway according to your needs and budget.

Popular places to visit

Grace Bay Beach showing a sandy beach

Grace Bay Beach

5/5(3 reviews)

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
Grace Bay Beach featuring tropical scenes, outdoor eating and general coastal views

Providenciales Beaches

Why not spend a lazy afternoon at Providenciales Beaches during your trip to Grace Bay? Amble around this romantic area's beautiful beaches or seek out the snorkelling spots.

Providenciales Beaches

Things to do

Clear Kayak Drone Photoshoot

Clear Kayak Drone Photoshoot

£108
per adult
80% of travellers recommend
Clear Kayak Drone Photoshoot
Clear Kayak Tour in Turks & Caicos Islands

Clear Kayak Tour in Turks & Caicos Islands

£86
per adult
Clear Kayak Tour in Turks & Caicos Islands
Shipwreck Adventure in Providenciales

Shipwreck Adventure in Providenciales

£160
per traveller
88% of travellers recommend
Shipwreck Adventure in Providenciales
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. Flight-inclusive packages are ATOL protected.