Top Villas in Windward in 2026

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Our top choices for Windward villas

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

Quartier Lorient

Mariem

2. Villa RIVA, luxury villa, magnificent sea view, 5 min from the beach, 2 swimming pools

Marigot

nicholas d.

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

Vitet

Julianne N.

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

Pointe Milou

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

Toiny

Fume L.

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

Pointe Milou

Anonymous traveler

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

Vitet

Edoardo M.

8. Villa Yvantino beachfront ( 2 bedroom )

Quartier Lorient

Shaun C.

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Top Windward Hotel Reviews

Lil' Home

10/10 Excellent

"The most beautiful villa, breathtaking views. The villa was impeccable clean and beautifully designed."

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."

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

10/10 Excellent

"Amazing, quiet property. Loved the roaming turtles, wildlife and the hosts pets. The pool was great to cool off after the beaches. Loved the open air kitchen with everything we needed and more. I would recommend this to anyone that is looking for quaint, non commercial vacation experience. Centrally located so easy access around the island."

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Check prices for these dates

Our top choices for Windward villas

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

2. Villa RIVA, luxury villa, magnificent sea view, 5 min from the beach, 2 swimming pools

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

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

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

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

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

8. Villa Yvantino beachfront ( 2 bedroom )

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

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

11. Beach 2 minutes' walk, private deck, tranquility

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

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

14. YVANTINO (6 BEDROOMS) BEACHFRONT & OCEAN

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

16. Villa LAGON JAUNE – Twin Villa Estate with 7 Bedrooms & Ocean Views in Petit Cul de Sac, St. Barths

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

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

19. NEW! Villa Vagabond Breathtaking Panoramic View & Caribbean Charm St-Barts 3 Bdr

20. Villa Jelo - 3 bdr - 2.5 bth - Pool & SPA - Games Room

Find vacation rentals that suit your style

Top Windward Hotel Reviews

Lil' Home

Rosewood Le Guanahani St Barth

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

Tropical Hotel St Barth

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

Amnios St Barth

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

Spacious Luxury 4 bedrooms, direct no agencies, fully renovated

One bedroom cottage located a step away from Saline beach

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