Leeward Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

Top Leeward Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Saint-Jean
Price was £6,024, price is now £4,869 per person
£4,869
per person
18 Dec - 23 Dec
found 1 day ago
Return flight included
London (LON) to Gustavia (SBH)
9.8/10 Exceptional! (135 reviews)

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Colombier
Price was £5,668, price is now £4,930 per person
£4,930
per person
18 Dec - 23 Dec
found 1 day ago
Return flight included
London (LON) to Gustavia (SBH)
9.8/10 Exceptional! (105 reviews)

Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Toiny
Price was £8,464, price is now £7,417 per person
£7,417
per person
18 Dec - 23 Dec
found 1 day ago
Return flight included
London (LON) to Gustavia (SBH)
9.8/10 Exceptional! (57 reviews)
My husband and I stayed here for our honeymoon and had the most beautiful villa! When we checked into our villa there was the most wonderful welcome gift and card. It was the perfect peaceful and quiet oasis to end our trip. We loved the shuttle that takes you down to their beach club and beach where you can have lunch and enjoy the ocean views. The beach was rocky so we didn’t swim, but there is a pool down by the beach as well. We absolutely loved that everything was Le Toiny branded. The private pool at our villa was amazing too! We will definitely be back. The staff was super friendly and accommodating as well!

Reviewed on 24 Oct 2026

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou
Price was £7,797, price is now £6,861 per person
£6,861
per person
18 Dec - 23 Dec
found 1 day ago
Return flight included
London (LON) to Gustavia (SBH)
9.6/10 Exceptional! (265 reviews)
Excellent stay for couples

Reviewed on 10 Nov 2026

Leeward Essential Information

Language
French
Currency
Euros
Local Welcome
Salut / Bonjour
Local Goodbye
Au revoir / À bientôt
Closest Airport
Gustaf III Airport (SBH)

Top hotels in Leeward

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Le Colombier St. Barthelemy
The price is £822 per night from 16 Nov to 17 Nov
£822
16 Nov - 17 Nov
includes taxes & fees
GYP SEA Saint Barth
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes St. Barthelemy
The price is £859 per night from 16 Nov to 17 Nov
£859
16 Nov - 17 Nov
includes taxes & fees
9.4/10 Exceptional! (71 reviews)
"Lovely, “barefoot chic” hotel that is top class in all respects"

Reviewed on 27 Apr 2026

Hotel Manapany
Reve de Saint Barth

Reve de Saint Barth

Les Hauts de Flamands, Merlette St. Barthelemy
9.8/10 Exceptional! (71 reviews)
"I would like to thank Ninon for an great experience while visiting the property at Rêve de St. Barth. We appreciated the innovative architectural design and felt like we were special how the staff treated us. Lovely setting in the hills of St.Barth with a view of the ocean from the second floor bedroom. ..."

Reviewed on 30 Sept 2026

Get rates
Reve de Saint Barth
See all 1,437 properties in Leeward
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.
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Frequently asked questions

How much does a Leeward travel package cost?
From as little as £4,869. Yes, you read that correctly. Our Leeward travel packages are an easy way to make your dollars go much further. Bundle your hotels, flights and rental car and explore this vibrant destination.
If I'm not able to travel, can I cancel my Leeward travel package?
Plans can change unexpectedly, so yes. You may be able to amend or cancel your Leeward travel package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still make changes, but your car rental company, airline or hotel may charge additional fees. Looking for more information? Look up our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Leeward?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Flights, hotels, rental cars and activities — we've got it all. Pick the combination that suits your style and see your savings grow. Of course, a package deal is never a one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 hotels across the world, which lets you customize your Leeward adventure.
Does Expedia offer Book Now, Pay Later Leeward holidays?
Yes. Expedia has teamed up with online lender Klarna to help you easily pay for your holiday in instalments. Simply select the payment plan that works for you during checkout and take the stress out of budgeting for your next trip. Be sure to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all budgets, so you can lock in that well-deserved holiday sooner.
  • Pay in instalments holidays: If you'd like to pay off your getaway in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Pressing the "book now" button is much easier with this payment plan. Just put down a small deposit on your holiday and then start working on your travel plans.

How far in advance should I book my Leeward holiday?
Reserving your flights early with Expedia means one less thing to worry about. Most carriers display prices up to 12 months prior to departure dates. This is generally the cheapest time to book. If circumstances have left you booking late, low prices to Leeward are still known to appear a few weeks before departure.
What does an Expedia Leeward travel package include?
Much of that is up to you. You can choose from a range of Leeward bundles, such as a flight, rental car and hotel. You can also book a flight and a hotel, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your Leeward trip looks like, you're sure to save!
What should I know before booking a Leeward travel package?
A travel package can be tailored to your budget and is a great way to make your budget go further. How much you include is totally up to you. Rental cars, hotels and flights — decide on a combination that suits your style.
Can I choose my airline with a Leeward Expedia travel package?
Most definitely. Expedia has access to more than 550 partner airlines around the world, so you can design your Leeward adventure according to your style and budget.

What to do in Leeward

St Maarten Beach hopping tour

St Maarten Beach hopping tour (Orient beach and Maho beach combo)

£45
per adult
St Maarten Beach hopping tour (Orient beach and Maho beach combo)
Seaview Beach Hotel Pool Pass/Cabana Rental

Seaview Beach Hotel Pool Pass/Cabana Rental

£15
per adult
Seaview Beach Hotel Pool Pass/Cabana Rental
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

£119
per adult
92% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
See all activities in Leeward

* 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.