Windward Holiday Rentals: Short-Term Accommodations for Rent

Our top choices for Windward holiday rentals

A modern outdoor lounge area with a pool, wooden deck, and seating arrangements overlooking the ocean.

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

Anse des Cayes

Jackson H.

HK$17,686 total

includes taxes & fees

9 Nov - 10 Nov

A covered outdoor dining area with a view of the sea and mountains.

2. 🏝REAL VILLA ON THE BEACH !SURFSPOT🏝CLOSE TO FLAMANS-STJEAN BEACH .REST.BARS

Anse des Cayes

Eric S.

HK$13,955 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Find holiday rentals that suit your style

Villas

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

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!"

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Windward holiday rentals

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

2. 🏝REAL VILLA ON THE BEACH !SURFSPOT🏝CLOSE TO FLAMANS-STJEAN BEACH .REST.BARS

Find holiday 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