Top Villas in Windward in 2026

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Our top choices for Windward villas

A modern house with a pool, wooden deck, and a covered patio area.

1. Modern villa, a 3-minute walk from St. Jean Beach, shops, and restaurants.

Saint-Jean

Michael D.

A wooden deck with a pool, lounge chairs, and a potted plant.

2. Modern Spacious Private Villa w/ Pool & Sunrise View

Vitet

Edoardo M.

A balcony with a table and chairs, a bowl of fruit, and a view of the sea and hills.

3. Villa YVANTINO OCEAN (4 bedrooms)—it feels like being on the deck of a boat

Quartier Lorient

Mariem

A covered outdoor seating area with a view of the sea, a hot tub, and a dining setup.

4. Villa Yvantino Right on the Beach (2 Bedrooms)

Quartier Lorient

Shaun C.

A wooden deck with a pool, a sofa, and a view of the ocean.

5. Beautiful 4-bedroom bohemian-style villa with sea view, perfect for sunset lover

Pointe Milou

A modern coastal house with a large glass window, wooden exterior, and a stone wall.

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

Toiny

Fume L.

A poolside area with a view of the sea, a wooden table, and chairs.

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

Marigot

Rob d.

A white sofa with beige cushions on a balcony overlooking a coastal view with palm trees and the ocean.

8. Spacious Luxury 4 bedrooms, direct no agencies, fully renovated

Pointe Milou

James C.

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Top Windward Hotel Reviews

Le Toiny Hôtel & Beach Club

10/10 Excellent

"My husband and I stayed here for our honeymoon and had the most beautiful villa! When we checked into our villa there was the most wonderful welcome gift and card. It was the perfect peaceful and quiet oasis to end our trip. We loved the shuttle that takes you down to their beach club and beach where you can have lunch and enjoy the ocean views. The beach was rocky so we didn’t swim, but there is a pool down by the beach as well. We absolutely loved that everything was Le Toiny branded. The private pool at our villa was amazing too! We will definitely be back. The staff was super friendly and accommodating as well!"

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."

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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Windward Villas information

Number of reviews	293
Accommodation	714 Villas
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Our top choices for Windward villas

1. Modern villa, a 3-minute walk from St. Jean Beach, shops, and restaurants.

2. Modern Spacious Private Villa w/ Pool & Sunrise View

3. Villa YVANTINO OCEAN (4 bedrooms)—it feels like being on the deck of a boat

4. Villa Yvantino Right on the Beach (2 Bedrooms)

5. Beautiful 4-bedroom bohemian-style villa with sea view, perfect for sunset lover

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

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

8. Spacious Luxury 4 bedrooms, direct no agencies, fully renovated

9. THE VILLA AFRICAN QUEEN - AN OASIS IN THE CARIBBEANS WITH A GIANT POOL !

10. Villa Jelo - Private Pool, Spa & Games Room - St Barts

11. Beach 2-minute walk away, private terrace, peaceful setting

12. Villa Kali - Villa for 2 - Pool, Wi-Fi, Spectacular View

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

14. Villa RIVA, luxury villa, stunning ocean view, 5 minutes to the beach, 2 pools

15. Villa in St. Jean - Spectacular view of the bay - Very private - 4 bedrooms

16. Villa Endeavour So private, breathtaking ocean views, direct from owner !

17. Villa Rayon de Soleil | Beach Front - Located in Stunning Flamands with Concierge Services

18. C'EST MA VUE by WIMCO St. Barth Properties

19. Villa Eclipse

20. YVANTINO (6 BEDROOMS) BEACHFRONT & OCEAN

Find holiday rentals that suit your style

Top Windward Hotel Reviews

Le Toiny Hôtel & Beach Club

Lil' Home

Le Barthélemy Hotel & Spa

Rosewood Le Guanahani St Barth

Villa YVANTINO OCEAN (4 bedrooms)—it feels like being on the deck of a boat

Villa Yvantino beachfront ( 2 bedroom )

Amnios St Barth

Modern Spacious Private Villa w/ Pool & Sunrise View

One bedroom cottage located a step away from Saline beach

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Windward Villas information