Owner Direct Vacation
Rentals in Windward

The Best Owner Direct Vacation Rentals in Windward. Explore thousands of vacation home rentals, large cabins, and villas near Windward

  1. Owner Direct
  2.  St. Barthelemy
  3.  Windward

Explore the Best Windward Vacation Homes

Looking for the perfect place to stay in Windward? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Windward character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.

  • vacation rentals
  • luxury villas
  • beachfront homes
  • pet-friendly rentals
  • condos

Why Travelers Love Using
Owner Direct to
Find Windward Vacation Rentals

What makes our vacation homes stand out?

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Verified Properties

Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

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Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Popular Neighborhoods for Windward Vacation Rentals

What are the best areas to stay in Windward

Discover the top neighborhoods in Windward and choose a place that suits your stay.

Monday Feb 9

Windward, St. Barthelemy

Mon
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25.1°C
Tue
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24.5°C
Wed
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24.6°C
Thu
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25.1°C
Fri
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25.7°C
Sat
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25.5°C
Sun
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25.6°C

Common Vacation Rental Amenities Typical Vacation Rental Amenities

What sort of amenities will be available at your stay?

Our Windward vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.

Indoor Amenities

  • indoor-amenities-kitchenFully equipped kitchens
  • indoor-amenities-living-areaSpacious living areas with streaming TVs
  • indoor-amenities-wifiComplimentary Wi-Fi
  • indoor-amenities-acAir conditioning and heating
  • indoor-amenities-washerIn-unit washer and dryer
  • indoor-amenities-bedPlush bedding and comfortable furniture

Outdoor Amenities

  • outdoor-amenities-balconyBalconies or patios with coastal views
  • outdoor-amenities-poolPrivate or shared pools
  • outdoor-amenities-bbqBBQ grills and outdoor dining areas
  • outdoor-amenities-parkingOn-site parking
  • outdoor-amenities-beachEasy access to beaches and attractions

How to Reserve Your Windward Vacation Rental

Booking Made Simple

Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.

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SEARCH PROPERTIES

Use filters for location, amenities, and budget.

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VIEW DETAILS

Check photos, reviews, and features for your top picks.

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BOOK SECURELY

Confirm your stay safely through our trusted travel partners.

Windward Vacation Rental FAQs

1. What are the top vacation rentals in Windward?

2. How many vacation rentals have private pools in Windward?

There are 2929 vacation rentals with private pools near Windward. Top-rated homes that have access to a swimming pool include:

3. Which vacation homes in Windward are best for families?

If you are looking for a family-friendly vacation home in Windward, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windward:

4. How many vacation rentals are available in Windward?

Currently, the total number of properties listed in 2026 is over 3548 in the Windward area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windward.