Leeward Settlement Holidays from £1,812

Book a Hotel + Flight or Car together to unlock savings

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.
Windsong on the Reef

Windsong on the Reef

4.5 out of 5
Grace Bay
Price was £2,503, price is now £1,812 per person
£1,812
per person
3 Dec - 6 Dec
found 1 day ago
Return direct flight included
London (LON) to Providenciales (PLS)
9.2/10 Wonderful! (1,310 reviews)
This resort is small, boutique feel, but boy do they go above and beyond! The staff is so so amazing, can’t say enough good things about them! Room and grounds are spotless and pool area always being cleaned! Food was good too! You can use your continental breakfast credit for the restaurant breakfast menu which tasted amazing !

Reviewed on 26 Oct 2026

Dream Villas Provo

Dream Villas Provo

3.5 out of 5
Blue Hills
Save 100% on your flight
Price was £9,692, price is now £6,042 per person
£6,042
per person
27 Dec - 3 Jan
found 1 day ago
Return direct flight included
London (LON) to Providenciales (PLS)
9.4/10 Exceptional! (82 reviews)

Beach Enclave

Beach Enclave

5 out of 5
Leeward Settlement
Save 100% on your flight
Price was £29,743, price is now £20,252 per person
£20,252
per person
27 Dec - 3 Jan
found 1 day ago
Return direct flight included
London (LON) to Providenciales (PLS)
8/10 Very good! (11 reviews)

SulMare at Taylor Bay Luxury Villas

SulMare at Taylor Bay Luxury Villas

4 out of 5
Price was £6,316, price is now £4,582 per person
£4,582
per person
7 Jan - 14 Jan
found 1 day ago
Return direct flight included
London (LON) to Providenciales (PLS)
10/10 Exceptional! (5 reviews)

Le Vele Resort

Le Vele Resort

4 out of 5
Grace Bay
Price was £4,615, price is now £3,475 per person
£3,475
per person
7 Jan - 14 Jan
found 1 day ago
Return direct flight included
London (LON) to Providenciales (PLS)
9.2/10 Wonderful! (69 reviews)
Clean room. Beautiful beach. Beautiful beach view from balcony. Very friendly staff

Reviewed on 23 Oct 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
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
The price is £580 per night from 27 Nov to 28 Nov
£580
27 Nov - 28 Nov
includes taxes & fees
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! (220 reviews)
"Although this property is beautiful, we were fooled into thinking our room had a view like shown on their reservation site. We had a view of the elevator. It was a ghost town, no snack bar, no drink bar, no room service and a tricky AC unit that wouldn’t function on cold for long. I would suggest ..."

Reviewed on 9 Aug 2026

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The Atrium Resort
Barefoot Luxury – Silver Palms Cottage # 1, Beachfront with Pool on Long Bay

Barefoot Luxury – Silver Palms Cottage # 1, Beachfront with Pool on Long Bay

providenciales Caicos Islands
Get rates
Barefoot Luxury – Silver Palms Cottage # 1, Beachfront with Pool on Long Bay
See all 1,746 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 £1,812. 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.

Stay near popular Leeward Settlement attractions

A beach with turquoise water, white sand, and rocky outcrops.
Photo by Staci Partlo
Open Photo by Staci Partlo

Leeward Beach

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

2 Hour Champagne Sunset Cruise from Grace Bay, Providenciales

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

£91
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

£121
per adult
94% of travellers recommend
Half-Day Snorkeling Cruise
Mangrove Cay Tour

Mangrove Cay Tour

£79
per adult
90% of travellers recommend
Mangrove Cay 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. Flight-inclusive packages are ATOL protected.