Leeward Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Vacation Rentals in in Leeward

Villa Vue mer Panoramique, à 5 Minute de la Plage !
Property grounds
Villa Vue mer Panoramique, à 5 Minute de la Plage !
10.0 out of 10, Exceptional, (1)
"We LOVED our stay at Villa Nagabaaja! It's one of those places where the reality is actually better than the photos! The renovations are spectacular, the kitchen is very well stocked with everything you can imagine and the new, modern bathrooms are fabulous! The welcome drinks and beach bags/totes were a special added touch, the view out of this world, outdoor space very well furnished and comfortable, and overall just a perfect stay. We'll definitely return!"
Villa Vue mer Panoramique, à 5 Minute de la Plage !
Superb studio for two, great location, fantastic sea view, affordable rate
Outdoor pool
Superb studio for two, great location, fantastic sea view, affordable rate
9.6 out of 10, Exceptional, (45)
"This property was a fantastic find. From the moment we entered the condo, a mood was set with music playing and an amazing view toward the beach beckoning us onto the patio. While modest in size, the unit had everything we needed. The view was stunning, the foliage and landscaping magical, and the location was an easy drive to anything we needed or wanted. The owner and manager were great communicators with us long before we even got to the property. A great umbrella, comfortable beach...
Superb studio for two, great location, fantastic sea view, affordable rate
Villa King Gustaf - Ocean & harbour view
Outdoor pool
Villa King Gustaf - Ocean & harbour view
10.0 out of 10, Exceptional, (1)
"We loved our stay here ! The location is great, the villa is beautiful and clean. "
Villa King Gustaf - Ocean & harbour view
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
SUNSET VILLA ANGEL ****
Terrace/patio
SUNSET VILLA ANGEL ****
10.0 out of 10, Exceptional, (11)
"Great View and modern property. Private pool and large deck area. Car is a must for this location."
SUNSET VILLA ANGEL ****
VILLA - POOL WITH DIVING VIEWS OVER THE OCEAN
On the beach, beach towels
VILLA - POOL WITH DIVING VIEWS OVER THE OCEAN
9.0 out of 10, Wonderful, (2)
"It was nice.. Had a great view. Manager always responded to my needs."
VILLA - POOL WITH DIVING VIEWS OVER THE OCEAN
IXORA VILLA ST. BARTH
Beach
IXORA VILLA ST. BARTH
9.6 out of 10, Exceptional, (22)
"Very nice property. Wonderful host."
IXORA VILLA ST. BARTH
Luxury villa with magnificent sea view
Dining
Luxury villa with magnificent sea view
10.0 out of 10, Exceptional, (19)
"We loved our stay at Villa Jali! The home is beautiful, and it was so nice having the pool on property. We enjoyed being able to escape the crowds and retreat to a quiet neighborhood, especially since our children were with us. And Clement was so helpful. He was just a call or text away at all times."
Luxury villa with magnificent sea view
On the Beach, in Saint Barth... Villa Mellow Mood
Beach/ocean view
On the Beach, in Saint Barth... Villa Mellow Mood
10.0 out of 10, Exceptional, (3)
"We stayed as a family with 2 children. I hope they were not too noisy. We loved our stay. The house was beautifully decorated, very well organized and very clean, it had everything we needed. We enjoyed watching sunset and boats every evening and our kids loved the cat that walked outside the house. The location was perfect for us, right on the beach! Would definitely come back!!"
On the Beach, in Saint Barth... Villa Mellow Mood
Villa Rose des Cayes in Saint Barthelemy with parking and private pool
Exterior
Villa Rose des Cayes in Saint Barthelemy with parking and private pool
10.0 out of 10, Exceptional, (1)
"Anniversaire de mariage, 40 ans, et Fan de Johnny Hallyday, anniversaire de sa mort, déjà 6 ans. Rencontre avec Laetitia. Découverte de cette très belle île."
Villa Rose des Cayes in Saint Barthelemy with parking and private pool
Located on the famous island of St. Barts, Villa Eugenie is a charming house.
Property grounds
Located on the famous island of St. Barts, Villa Eugenie is a charming house.
10.0 out of 10, Exceptional, (3)
"The villa was perfect and only a short distance from Gustavia. The yard and jacuzzi were very relaxing. Laurent and Axel were wonderful and so helpful. I highly recommend this property. Karen"
Located on the famous island of St. Barts, Villa Eugenie is a charming house.
beautiful architect villa
Outdoor pool, a heated pool
beautiful architect villa
9.8 out of 10, Exceptional, (21)
"As a family of five with a 16 year old teen, and 2 twenty somethings, my husband and I rented the villa to celebrate a special anniversary. Upon arrival we were greeted by Clement who accompanied us to the villa and helped us with our baggage. When we arrived, we were stunned by the beautiful infinity pool against the gorgeous ocean. The villa had 4 beautiful bedrooms and baths, each room the same size, 2 up and 2 down. The bedrooms had nice air conditioning to sleep comfortably. The open space...
beautiful architect villa
Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool
Beach nearby
Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool
10.0 out of 10, Exceptional, (4)
"We had an amazing time staying at this appointments. It has everything what you need. Also it has an absolute gorgeous view on the island from the main floor and stunning long window. From a bedroom . It was super clean, convenient and stylish . We would love to come back again and stay there. Definitely one of the gems"
Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool
Villa VOGUE - Panoramic Ocean View - St Jean
Terrace/patio
Villa VOGUE - Panoramic Ocean View - St Jean
10.0 out of 10, Exceptional, (15)
"Sarah is a superhost!! We had an incredible trip, and our housekeeper and Sarah were absolutely amazing team. They provided all the help we could need. We traveled with a toddler and four adults, and this house was a perfect fit! The property, which was gorgeous, had all the essentials - and more! Overall, I would highly recommend staying at Villa Vogue. Our favorite restaurants were Bonito and La Case at Cheval Blanc."
Villa VOGUE - Panoramic Ocean View - St Jean
Ocean views villa Lo Scoglio
Pool
Ocean views villa Lo Scoglio
Ocean views villa Lo Scoglio
Beautiful, secluded studio minutes from the beach
Property grounds
Beautiful, secluded studio minutes from the beach
Beautiful, secluded studio minutes from the beach
Beautiful, beach-front, two-bedroom villa
Property grounds
Beautiful, beach-front, two-bedroom villa
Beautiful, beach-front, two-bedroom villa
Unique style loft, With spa-150 mètres to the beach
Outdoor spa tub
Unique style loft, With spa-150 mètres to the beach
10.0 out of 10, Exceptional, (9)
"Our stay was just perfect. The accommodation is in such a great location. We were able to walk to everywhere in Gustavia. If we needed a taxi, our incredible host, Rudy sorted us one. All the amenities were fantastic and made for such a great stay. Rudy was just fabulous throughout. I honestly cannot recommend this property more. We will be back! "
Unique style loft, With spa-150 mètres to the beach
Villa Natanya (2 bedrooms)
Property grounds
Villa Natanya (2 bedrooms)
10.0 out of 10, Exceptional, (1)
"All went very well."
Villa Natanya (2 bedrooms)
Private, hill-side getaway 1 bedrooms with amazing views
Property grounds
Private, hill-side getaway 1 bedrooms with amazing views
Private, hill-side getaway 1 bedrooms with amazing views
Luxury Retreat in Paradise
View from property
Luxury Retreat in Paradise
Luxury Retreat in Paradise
Don't see what you're looking for?
See all available 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.

Everything you need to know about Leeward vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Leeward vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leeward vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Leeward vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leeward. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Leeward vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Leeward vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Leeward rentals

At Expedia, we put the best Leeward vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Leeward rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leeward vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leeward. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Leeward Vacation Rental Travel Info

Vacation rentals
24
Popular accommodation
Leeward villas
International airport
Gustavia (SBH-Gustaf III)

Recent reviews in Leeward
Expedia verified reviews

GYP SEA Saint Barth

GYP SEA Saint Barth

5/5 Excellent
"Property had the most gorgeous views of St Barths and had a gym as well as an excellent beach inclusion. Only difficulty is that the beach is about a 10 minute drive from the hotel and you need a car (which most people need a car anywhere they stay in St Barths anyways). Otherwise excellent stay and staff was fabulous (shout out to Manon who made our stay very welcoming!)"
A verified traveller stayed at GYP SEA Saint Barth
Posted 3 days ago
GYP SEA Saint Barth