Top Vacation Homes in Windward in 2026

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Our top choices for Windward vacation homes

A clear swimming pool with a stone edge, surrounded by lush tropical plants and a building in the background.

1. NEW, INTIMATE BUNGALOW WITH POOL

Pointe Milou

Steve B.

A clear swimming pool with a curved edge, surrounded by lounge chairs and a wooden deck.

2. One bedroom cottage located a step away from Saline beach

Grande Saline

Jessica D.

3. 1 bedroom cottage located a step away from Saline Beach in St-Barth.

Grande Saline

"Charming cottage, set on beautiful, quiet gardens. The pool cabanas were a god send during the passing showers. Cat is a gracious host. Communication (via WhatsApp) was easy. Location is ideal for a relaxing holiday. Saline feels like the "quite" side of the island, but still walking distance to a couple of the best restaurants on the island (The risotto at La Tamarin was our best meal). Would love to stay here again. "

Mike V.

A wooden deck with a table and chairs, a hanging hammock, and a rock with aloe plants.

4. Very quiet neighborhood near kite and surf spot. Price is for 2 bedrooms

Grand Cul-de-Sac

Jon A.

A balcony with a pool, lounge chairs, and a view of the ocean and hills.

5. Beautiful 3 en-suite bedrooms villa with lagoon views

Grand Cul-de-Sac

Bethany S.

A kitchen with wooden cabinets, a white countertop, a sink, and a window with a view of greenery.

6. Lodge Kaz à Sucre .

Grande Saline

Joseph D.

A cozy cabin with a wooden exterior, a small bedroom with a bed, a kitchenette, and a deck area.

7. Lodge Liberty .

Grande Saline

A house with a stone patio, a dining table, and chairs.

8. Oceanfront Home in St Barth, 2BR — Steps from the water / Petit-Cul-de-sac

Grand Cul-de-Sac

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Top Windward Hotel Reviews

Le Barthélemy Hotel & Spa

10/10 Excellent

"One of the best hotels that I stayed with my wife in the Caribbean."

Le Toiny Hôtel & Beach Club

10/10 Excellent

"Le Toiney is everything you can dream of for a vacation. The level of service & the beauty of the property is extraordinary. The staff go above & beyond providing exceptional service. The food is great & the rooms are very nice. Not to mention how special they made my birthday. It makes you want to stay at Le Toiney over & over. Actually I didn’t want to leave."

Rosewood Le Guanahani St Barth

8/10 Good

"Our experience at Rosewood Le Guanahani St. Barth was mixed. The property is beautiful, very well maintained, and in a stunning location. We encountered several friendly and helpful staff members, and the team was especially helpful with arranging taxis and transportation around the island. Unfortunately, one incident significantly affected our overall impression. While at the pool, a staff member told us that the lounge chairs were for “hotel guests,” in a way that made us feel as though we were not guests ourselves. Regardless of the intention, the comment felt discriminatory and was extremely uncomfortable and disappointing. At a luxury property of this caliber, every guest should feel welcomed, respected, and valued. We reported the incident to the manager, who offered a sincere apology and kindly offered to cover our lunch as a gesture of goodwill. We appreciated the manager taking the matter seriously and attempting to make amends. However, the gesture did not erase how the incident made us feel, especially because this should never have happened at such a high-end, well-established hotel. We also found the restaurant options somewhat limited, with less variety and diversity than expected from a luxury resort. Overall, the property is beautiful and has some excellent staff, but this unfortunate incident overshadowed many of the positives. We hope the hotel takes this feedback seriously so that every guest receives the same level of respect and hospitality."

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

10/10 Excellent

"Mr. Strokirk,What a pleasure to visit your beautifully designed home-Thank you!The architectural details showing camera-like lens views out the large windows were so well thought out!Franscoise met us early when our flight was changed and gave a review of the home, leaving us with a pleasant surprise gift of wine and excellent cheeses-thank you!Maria worked diligently each day keeping the home clean. While my wife and I leave a clean footprint wherever we visit, Maria made sure the home was spotless-thank you!We are grateful and hope to return soon!The setting was unparalleled…steps to the beach, mountain vistas, and mesmerizing waves. Your home will be our go-to on return visits."

Modern Spacious Private Villa w/ Pool & Sunrise View

10/10 Excellent

"We loved it! Is beautiful,looks brand new, beautifully decorated,spacious gorgeous ocean and mountains view, very quiet and private,super close to all the points of interest, our hostess Lilly was amazing. We can’t wait to come back!! 10/10!"

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Check prices for these dates

Our top choices for Windward vacation homes

1. NEW, INTIMATE BUNGALOW WITH POOL

2. One bedroom cottage located a step away from Saline beach

3. 1 bedroom cottage located a step away from Saline Beach in St-Barth.

4. Very quiet neighborhood near kite and surf spot. Price is for 2 bedrooms

5. Beautiful 3 en-suite bedrooms villa with lagoon views

6. Lodge Kaz à Sucre .

7. Lodge Liberty .

8. Oceanfront Home in St Barth, 2BR — Steps from the water / Petit-Cul-de-sac

9. Bungalow CAZ A Saline N°2

10. Lodge La Case .

11. Lodge Freedom .

12. Oasis Zen 1

13. Tranquil 1-bedroom bungalow in Saint-Barthélemy

14. Villa JELO - 1BR - Private Pool & Spa - Perfect for Couples

15. Villa JELO - 2BR - Private Pool, Spa & Game Room

Find vacation rentals that suit your style

Top Windward Hotel Reviews

Le Barthélemy Hotel & Spa

Le Toiny Hôtel & Beach Club

Rosewood Le Guanahani St Barth

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

Amnios St Barth

Modern Spacious Private Villa w/ Pool & Sunrise View

One bedroom cottage located a step away from Saline beach

La Maison Fleur de Lune

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