Leeward Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

Top Flight + Hotel Deals in Leeward

Price found within the past 48 hours. Click for updated prices.
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou
Price was €5,814, price is now €5,424 per person
€5,424
per person
21 Jul - 24 Jul
found 20 hours ago
Return flight included
Dublin (DUB) to Gustavia (SBH)
9.6/10 Exceptional! (242 reviews)
Awesome property , peaceful and beautiful views

Reviewed on 5 Jun 2026

Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Saint-Jean
Price was €6,004, price is now €5,527 per person
€5,527
per person
21 Jul - 24 Jul
found 20 hours ago
Return flight included
Dublin (DUB) to Gustavia (SBH)
9.8/10 Exceptional! (120 reviews)
As usually, Simply Perfect stay in every aspect.

Reviewed on 21 May 2026

Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was €6,254, price is now €5,831 per person
€5,831
per person
21 Jul - 24 Jul
found 20 hours ago
Return flight included
Dublin (DUB) to Gustavia (SBH)
9.4/10 Exceptional! (71 reviews)
365 degrees of beauty the eye wanders off to more and more beauty! The staff is excellent, kind and so so lovely! The concierge took care of our every need! We’re definitely going to stay again!

Reviewed on 16 Mar 2026

Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Toiny
Price was €6,921, price is now €6,558 per person
€6,558
per person
21 Jul - 24 Jul
found 20 hours ago
Return flight included
Dublin (DUB) to Gustavia (SBH)
9.8/10 Exceptional! (50 reviews)
Property is beautiful. The staff is very courteous. The concierge was excellent with restaurant and site seeing suggestions. Truly enjoyed our stay.

Reviewed on 8 Jun 2026

Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Grand Cul-de-Sac
Price was €8,426, price is now €8,032 per person
€8,032
per person
21 Jul - 24 Jul
found 20 hours ago
Return flight included
Dublin (DUB) to Gustavia (SBH)
9.8/10 Exceptional! (88 reviews)
Amazing hotel / resort!!! I really can’t stop telling everyone great things about this place! The service is by far the best service I have ever had. It’s so clean, amazing layout, perfect location! Such nice people, everyone is so eager to help you with your every wish. The food is delicious, drinks on point… this place is a dream come true. Recommended 20/10!

Reviewed on 26 May 2026

Top hotels in Leeward

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Le Colombier St. Barthelemy
The price is €681 per night from 1 Jul to 2 Jul
€681
1 Jul - 2 Jul
includes taxes & fees
9.8/10 Exceptional! (97 reviews)
"Beautiful"

Reviewed on 16 Jun 2026

GYP SEA Saint Barth
Fouquet's Saint-Barth

Fouquet's Saint-Barth

5 out of 5
Rue des Normands, Lieu Dit Lurin St. Barthelemy Leeward
The price is €1,276 per night from 16 Jul to 17 Jul
€1,276
16 Jul - 17 Jul
includes taxes & fees
9.8/10 Exceptional! (35 reviews)
"Great location, luxury and very comfortable room with great terrace and best view in St Barts. Will be back!"

Reviewed on 25 May 2026

Fouquet's Saint-Barth
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058 St. Barthelemy French West Indies
The price is €567 per night from 17 Jun to 18 Jun
€567
17 Jun - 18 Jun
includes taxes & fees
9.4/10 Exceptional! (201 reviews)
"Pearl Beach Hotel is one of a kind. We went for my girlfriends birthday and loved every minute of our stay. The staff was amazing throughout our time there - they were attentive, patient and helpful. The manager and front desk staff were awesome and always pleasant. The room was immaculate and spacious. ..."

Reviewed on 8 Jun 2026

Pearl Beach Hotel
See all 1,454 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.

Frequently asked questions

How much does a Leeward holiday package cost?
The most affordable Leeward holiday package is €5,424, so the trip of your dreams can become a reality — without burning a hole in your pocket. Combine flights, hotels and car rentals to customize a package that matches your travelling style.
How do I get a cheap travel package to Leeward?
Crafting your own Leeward holiday package with Expedia is one of the best ways to save. We offer access to over 550 air carriers and 1,000,000 properties across the globe. With such an amazing range to select from, you'll have no trouble pulling together your perfect getaway.
How far in advance should I book my Leeward holiday?
Get rewarded with the widest variety and the cheapest prices by booking your Leeward adventure early. Air carriers generally release flight tickets around a year before departure, so reserve your spot as soon as you can. That said, Expedia is committed to giving you the best deals around, so it's always a good time to book your dream holiday!
What does an Expedia Leeward travel package include?
Hotels, flights and a shiny set of wheels for all your fun road trip adventures. Simply choose your favourite bundle and gain access to great discounts. Once you've made your booking, add on a couple of experiences and tours and watch your savings grow. When it comes to creating your Leeward escape, you're the one in control!
What should I know before booking a Leeward travel package?
A package can be easier on the bank balance than separately booking all you need for your trip. For example, combine your flights, hotels and rental cars and save a packet. No matter your holiday plans, there's bound to be a package that best suits your budget.
Can I choose my airline with a Leeward Expedia holiday package?
Yes, you're in control. We offer more than 550 partner airlines globally, so you can customize your Leeward holiday according to your needs and budget.
If I'm not able to travel, can I cancel my Leeward holiday package?
Don't worry if you're rethinking your Leeward holiday package — you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We get that your circumstances can suddenly change, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.