Leeward Vacation Rentals

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Top Vacation Rentals in in Leeward

Villa Rosebud, 2BR, 2BA, (Sleeps 2-4), on the beach of Anse Des Cayes

9.8 out of 10, Exceptional, (45)
"Second time at Villa Rosebud. Wonderful house in a great location. Great communication before and during our stay. "
Villa Rosebud, 2BR, 2BA, (Sleeps 2-4), on the beach of Anse Des Cayes

🏝REAL BEACH VILLA ON THE BEACH !🏝CLOSE TO FLAMANS-ST JEAN BEACH CITY.REST.BARS

10.0 out of 10, Exceptional, (82)
"Great villa in an amazing location on the beach."
🏝REAL BEACH VILLA ON THE BEACH !🏝CLOSE TO FLAMANS-ST JEAN BEACH CITY.REST.BARS

Villa Vue mer Panoramique, à 5 Minute de la Plage !

9.8 out of 10, Exceptional, (6)
"Wonderful stay! "
The price is CA $2,248
CA $2,845 total
includes taxes & fees
Sep 1 - Sep 2
Villa Vue mer Panoramique, à 5 Minute de la Plage !

Located on the famous island of St. Barts, Villa Eugenie is a charming house.

10.0 out of 10, Exceptional, (5)
"Fabulous stay at a lovely villa with a great host, who made everything comfortable and seamless including assistance with a rental car and providing some great insights into the island. Would certainly stay again. "
Located on the famous island of St. Barts, Villa Eugenie is a charming house.

WATERFRONT PRIVATE ESTATE ! CHECK OUR REVIEWS 95% RETURNING GUESTS WALK TO BEACH

10.0 out of 10, Exceptional, (64)
"We came over from our place on St. Martin for a few days and had a wonderful time."
WATERFRONT PRIVATE ESTATE ! CHECK OUR REVIEWS 95% RETURNING GUESTS WALK TO BEACH

Appartement Vina, un Cocon Entre mer D'azur et Végétation Luxuriante

Appartement Vina, un Cocon Entre mer D'azur et Végétation Luxuriante

Lovely Villa Rose des cayes in Saint Barthélémy with parking and private pool

10.0 out of 10, Exceptional, (2)
"Loved our 10 days in St. Barths. Villa Rose des Cayes was the perfect home base to explore the beaches, visit the towns and go shopping. It's a beautiful house, fully equipped in a quiet yet central location. The owner is very nice. He met us at the airport and was available to address any issue."
Lovely Villa Rose des cayes in Saint Barthélémy with parking and private pool

Villa Privilege | Water View - Located in Beautiful Gustavia with Private Pool

Villa Privilege | Water View - Located in Beautiful Gustavia with Private Pool

On the Beach, in Saint Barth... Villa Mellow Mood

10.0 out of 10, Exceptional, (5)
"Great location! Beautiful sunsets over the harbor.. clean villa I will definitely be back!"
On the Beach, in Saint Barth... Villa Mellow Mood

Beautiful 2-bedroom apartment in Gustavia with harbor view in Saint Barthélémy

10.0 out of 10, Exceptional, (4)
"Very good location "
Beautiful 2-bedroom apartment in Gustavia with harbor view in Saint Barthélémy

Luxury villa with magnificent sea view

10.0 out of 10, Exceptional, (26)
"We had an absolutely wonderful stay at this beautiful villa. The views are gorgeous, the pool is great (and warm), and our every last need was taken care of (thank you Clement!) The location is pretty perfect too: central, and close to beaches and town. We truly hated to leave...and will definitely return."
Luxury villa with magnificent sea view

Saint Barths: brand new, luxury, architect-designed villa

10.0 out of 10, Exceptional, (22)
"Very nice, solidly constructed, very well appointed, great view and pool. Spacious, perfect for four. Would come back again."
Saint Barths: brand new, luxury, architect-designed villa

🏝 BEACH VILLA CENTRAL LOCATION BETW ST JEAN 🏖 FLAMMANS BEACH 4 min TO CITY

10.0 out of 10, Exceptional, (9)
"We had a wonderful stay at this beautiful place on the beach. Joce was very friendly and helpful - he even drove some of us to the airport when we couldn't fit all of our bags in the car. The place is so relaxing and beautiful, we had trouble leaving even to see other parts of the island."
🏝 BEACH VILLA CENTRAL LOCATION BETW ST JEAN 🏖 FLAMMANS BEACH 4 min TO CITY

SUNSET VILLA ANGEL ****

10.0 out of 10, Exceptional, (13)
"Great View and modern property. Private pool and large deck area. Car is a must for this location."
SUNSET VILLA ANGEL ****

Villa VOGUE - Panoramic Ocean View - St Jean

10.0 out of 10, Exceptional, (20)
"This is our 3rd time to the island, we previously stayed at Cheval Blanc but wanted to try out a villa. We could not have had a better experience. Sarah was amazing and communicating all details, Nicolas helped us on the spot when we could not find the house in our Moke. Villa Vogue is beautiful, well decorated, clean, each room has privacy. The view is unmatched. Sarah gives us a recommendation for Chef Julie who was outstanding. We will absolutely return."
Villa VOGUE - Panoramic Ocean View - St Jean

Villa Vogue (5 bedrooms)

Villa Vogue (5 bedrooms)

IXORA VILLA ST. BARTH

9.6 out of 10, Exceptional, (22)
"Very comfortable, clean and well outfitted for a couple to enjoy the island on a reasonable budget!"
IXORA VILLA ST. BARTH

Villa Cinnamon sunset and sea view

Villa Cinnamon sunset and sea view

Villa King Gustaf

Villa King Gustaf

Unique style loft, With spa-150 mètres to the beach

10.0 out of 10, Exceptional, (18)
"Wonderful property and host! the loft was perfect and had everything you could need - including snorkels and masks, umbrellas and chairs for the beach. A speaker to play music and a backgammon board and all kitchen utensils and coffee items. The deck and jacuzzi made the loft - such a beautiful setting and quiet too. Perfect location - safe and convenient to town and beach. Rudy our host was there at a moments notice and friendly and polite. "
Unique style loft, With spa-150 mètres to the beach
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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Top Leeward Hotel Reviews

Find out more about Leeward

Find out more about Leeward

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 CA $2,248 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia