Leeward Cottage Rentals
Villa
- Air Conditioner
- Parking
- Pet Friendly
House
- Air Conditioner
- Parking
- Pet Friendly
Villa
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- Pool
Apartment
- Air Conditioner
- Parking
- Pet Friendly
Villa
- Air Conditioner
- Parking
- Pet Friendly
Villa
- Air Conditioner
- Parking
- Pool
Why Choose Rent By Owner for your Leeward Cottage Rentals?
What makes our Cottage Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Leeward
How to Book Your Leeward Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Leeward
Common Cottage Rentals Amenities
What amenities can you expect?
Our Cottage Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Leeward
Gustavia
Grande Vigie
Flamands Beach
Anse des Flamands
Saint-Jean
Terre Neuve
Anse des Lezards
La Grande Montagne
Anse des Cayes
Public
Colombier
Frequently Asked Questions About Leeward Rental Cottages
1. What are the top Cottages in Leeward?
There are a lot of options in Leeward. If you plan on staying in the Leeward area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Leeward:
- The Perfect View of Anse de Cayes/St Jean Beach
- VILLA ANGEL ROCK
- On the Beach, in Saint Barth. Villa Mellow Mood
- Located on the famous island of St. Barts, Villa Eugenie is a charming house.
- Studio with separate entrance 3 minutes from the beach
- Villa Micela - Two Bedroom Beachfront Villa With Pool - St Barts Flamands Beach
- Secluded and Romantic Villa Overlooking St. Jean Bay
- Beautiful 2-bedroom apartment in Gustavia with harbor view in Saint Barthélémy
- Picturesque Villa W/Beautiful Sunset Views Directly Over Shell Beach & Gustavia
- Blue Swan - Luxury 4 Bedroom Villa in Lurin St Barts
2. How many Cottages are available in Leeward?
Currently, the total number of properties listed by RBO in 2026 is over 2378 in the Leeward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Leeward.
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