Vacation Rentals in Windward

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Top Vacation Rentals in Windward

NEW, INTIMATE BUNGALOW WITH POOL

Marigot
10.0 out of 10, Exceptional, (3)
"Even more beautiful than photos. Great location "
United States
Jeffrey A.
NEW, INTIMATE BUNGALOW WITH POOL

Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool

Saint Jean
9.4 out of 10, Exceptional, (11)
"The room was clean, the views spectacular!"
United States
Milton
Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool

1 bedroom cottage located a step away from Saline Beach in St-Barth.

Saint Barthelemy
9.8 out of 10, Exceptional, (22)
"Cat's villa is exactly what we were looking for - close to Saline beach and away from the busy crowds. We enjoyed waking up early morning to make coffee in the outdoor kitchen and taking a walk along the beach. Joelle was an amazing host, assisting us with everything we needed but giving us privacy to enjoy the space. We left with fond memories and would love to return again!"
United States
Manu M.
1 bedroom cottage located a step away from Saline Beach in St-Barth.

Sweet Hill Villa Alba

saint barthelemy
10.0 out of 10, Exceptional, (4)
"This was an amazing property! Very clean, beautiful view, had everything we needed, good response from the host. We have no complaints! Thank you for a wonderful stay!"
United States
Haley T.
Sweet Hill Villa Alba

BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach

Anse de Marigot
10.0 out of 10, Exceptional, (49)
"We enjoyed staying at the villa. It was perfect for our needs."
United States
D T D.
BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach

One bedroom cottage located a step away from Saline beach

Saline
10.0 out of 10, Exceptional, (25)
"Cat's cabin is cozy, safe and incredibly peaceful! Located super close to the amazing Saline beach! Perfect getaway on St. Barth's!"
United States
Kristina G.
One bedroom cottage located a step away from Saline beach

Appartement St Jean, Saint-barthélemy

St Jean
10.0 out of 10, Exceptional, (3)
"Very comfortable apartment, well-stocked kitchen. Lovely beach (St Jean) accessed via Eden Rock property several blocks away. Great price for this expensive island. L'Oasis supermarket and Le Choisy bakery (bkfst & lunch items) 1 mile away. Very busy street, lively at night, but apartment well-insulated. Parking could be challenging. Two reasonable restaurants right downstairs (Le Piment and Irish Pub). "
United States
Mara
Appartement St Jean, Saint-barthélemy

Bungalow CAZ A Saline

Grande Saline
9.0 out of 10, Wonderful, (4)
"Beautiful, peaceful , cozy cottage in a great location. Only a short walk to Saline beach and 2 nearby restaurants. Cottage was perfect for a couple and immaculate. Host is great, highly recommend for St Barthes getaway. "
United States
Russell G.
Bungalow CAZ A Saline

Indigo cosy seaside apartment 5 mn from saint jean beach swimming pool sea view

St Barthélemy
Indigo cosy seaside apartment 5 mn from saint jean beach swimming pool sea view

Villa YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat

Saint-Barthélemy
9.6 out of 10, Exceptional, (8)
"Nice front Beach property "
United States
Mariem
Villa YVANTINO OCEAN (4 bedrooms) the feeling of being on the deck of a boat

St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive

TOINY
9.8 out of 10, Exceptional, (52)
"Great house and team. Amazing views. House manger Francois will take care of your every need. We have been coming to the island for 25 years and one of the best acccomodations ever!"
United States
Brian M.
St Barts New Luxury Villa Roc E Mar, Fantastic Ocean View, Large Pool, Exclusive

Jelo House - 3 bdr - 2.5 bth - Pool & SPA - Sports & Games Room

SAINT BARTHELEMY
10.0 out of 10, Exceptional, (7)
"Our family really enjoyed our stay at Jelo! It is a wonderful place, decorated nicely with all the amenities a family would need. Patrice is an excellent concierge. "
United States
Vesna C.
Jelo House - 3 bdr - 2.5 bth - Pool & SPA - Sports & Games Room

Bungalow

Gustavia
Bungalow

Villa St Jean, 2 steps from Eden Rock (1 Bedroom)

Saint-Barthélemy
10.0 out of 10, Exceptional, (3)
"Great place. Great location. Very happy to have taken the place "
United States
Greg S.
Villa St Jean, 2 steps from Eden Rock (1 Bedroom)

Indigold - A Deux pas de la Plage Chambre Indépendante Avec Espace Détente

Marigot
9.2 out of 10, Wonderful, (5)
"Had such an amazing experience at indigo - the host was super accommodating and helpful. She went above and beyond to make sure that everything ran super smoothly. Will absolutely be coming back and staying with them again. "
United States
Kendall M.
Indigold - A Deux pas de la Plage Chambre Indépendante Avec Espace Détente

Lovely 2 bedrooms apartment, sea view and infinity pool

St Jean
9.4 out of 10, Exceptional, (13)
"A wonderful spot that i would highly recommend. And the host was fantastic. "
United States
kathleen t.
Lovely 2 bedrooms apartment, sea view and infinity pool

Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view

Saint-Jean
10.0 out of 10, Exceptional, (6)
"Had a great time staying in the villa. It’s pristine clean, great location and gorgeous views. If u come back to St Barth again, I’ll stay at the villa again! "
United States
Dinara S.
Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view

Beach 2 minutes' walk, private deck, tranquility

SAINT-BARTHELEMY (ILE)
10.0 out of 10, Exceptional, (1)
"Excellent séjour Maison confortable, bien agencée avec un jardin très beauSituation impeccable proche du Monoprix et d une boulangerie Et surtout des hôtes super gentils"
France
valérie p.
Beach 2 minutes' walk, private deck, tranquility

ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING

Pointe Milou
10.0 out of 10, Exceptional, (55)
"Great villa and host. Property needs a little tlc but overall the stay was sublime"
United States
chris s.
ST BART LUXURY VILLA SKRUTTEN, WITH OCEAN VIEW AND CONTEMPORARY FURNISHING

Villa Yvantino beachfront ( 2 bedroom )

Saint-Barthélemy
10.0 out of 10, Exceptional, (5)
"Great location on the water."
United States
Tzvetelina P.
Villa Yvantino beachfront ( 2 bedroom )
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windward Hotel Reviews

Find out more about Windward

Discover your perfect Windward vacation rental with Expedia

How many vacation rentals are available in Windward?


Expedia has plenty of vacation rentals to choose from in and around  Windward, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Windward?


The selection of Windward 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!


What type of vacation rental can I get in Windward?


Vacation rentals in Windward come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Windward vacation rentals to suit everyone. 


Why should I choose a vacation rental in Windward?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Windward 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. 


How do I find the best deal on a vacation rental in Windward?


Find vacation rentals in Windward by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Windward.  


What amenities are available in a vacation rental in Windward?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Windward vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Windward?   


Everytime is a great time to head to Windward! Staying in a Windward vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Windward. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Windward vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Windward, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Windward vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.  


Explore a world of travel with Expedia