Leeward Short-Term Rentals

Leeward Short Term Stay

Villa

Villa Arc En Ciel, Exotic Retreat On St. Barts

10.0

Exceptional

(2 Reviews)

4 Bedrooms 4 Baths 8 Guests 3500 ft²

R22,172/Night 7 Nights - R155,203

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Villa

Villa Wastra | Ocean View - Located in Wonderful Gustavia with Private Pool

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 4 Guests

R12,932/Night 7 Nights - R90,528

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Villa

Chef included by Fantasia Villas: Villa Gustavia Views

4 Bedrooms 3 Baths 7 Guests

R69,950/Night 7 Nights - R489,656

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Villa

Villa Wastra by Fantasia Villas

2 Bedrooms 2 Baths 4 Guests

R17,133/Night 7 Nights - R119,926

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Villa

Villa Wastra | Ocean View - Located in Tropical Gustavia with Private Pool

1 Bedroom 1 Bath 2 Guests

R12,932/Night 7 Nights - R90,528

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Villa

Gustavia Views (2/4 Rooms)

2 Bedrooms 4 Baths 4 Guests

R153,795/Night 7 Nights - R1,076,565

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Villa

Amancaya in Anse des Cayes by Personal Villas - Asian Inspired Decor, Pool, Cont

7 Bedrooms 6 Baths 14 Guests 3230 ft²

R116,779/Night 7 Nights - R817,452

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Villa

Gustavia Views Luxury villa

4 Bedrooms 3 Baths 8 Guests

R72,849/Night 7 Nights - R509,945

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Villa

Gustavia Views (3/4 Rooms)

3 Bedrooms 3 Baths 6 Guests

R66,215/Night 7 Nights - R463,505

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Villa

holiday vacation villa Caribbean, st. barts, st. barths, pool, wi-fi internet, view, garden, walk to beach, short term l

3 Bedrooms 3 Baths 6 Guests

R28,023/Night 7 Nights - R196,161

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Villa

Modern villa with warmed pool - 5 min from the beach !n2 bedrooms on 2 levels.

2 Bedrooms 3 Baths 4 Guests 1292 ft²

R16,946/Night 7 Nights - R118,617

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

Highly Rated

Villa

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

10.0

Exceptional

(86 Reviews)

3 Bedrooms 3 Baths 6 Guests 1600 ft²

R25,825/Night 7 Nights - R180,775

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More Top-Rated Short Term Stay in Leeward Area

Why Choose Rent By Owner for your Leeward Short Term Stay?

What makes our Short Term Stay 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.

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How to Book Your Leeward Short Term Stay

What's our booking process?

Our platform allows you to browse a curated selection of short term stay. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Leeward

More Top-Rated Short Term Stay in Leeward Area

Common Short Term Stay Amenities

What amenities can you expect?

Our Short Term Stay 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

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Frequently Asked Questions About Leeward Short-term Rentals

1. What are the top Short Term Stays 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 Short Term Stays in Leeward:

2. How many Short Term Stays are available in Leeward?

Currently, the total number of properties listed by RBO in 2026 is over 11 in the Leeward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Short Term Stays in Leeward. 