Owner Direct Vacation
Rentals in Windward Side

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

Explore the Best Windward Side Vacation Homes

Looking for the perfect place to stay in Windward Side? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Windward Side 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
8.1 (224 Reviews)
Hotel
El Momo Cottages
  • Pool
  • Designated Smoking Area
  • View
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7.9 (96 Reviews)
Apartment
The Old Gin House
  • Air Conditioner
  • Parking
  • Pool
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8.4 (14 Reviews)
Apartment
Palm Spring Inn
  • Air Conditioner
  • Pet Friendly
  • Bedding/Linens
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7.5 (69 Reviews)
Cabin
Statia Lodge
  • Parking
  • Pet Friendly
  • Pool
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7 (12 Reviews)
Apartment
Palm Spring Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Travelers Love Using
Owner Direct to
Find Windward Side 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 Side Vacation Rentals

What are the best areas to stay in Windward Side

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

Wednesday May 13

Windward Side, Bonaire

Wed
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26.8°C
Thu
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26.8°C
Fri
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26.7°C
Sat
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26.8°C
Sun
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26.8°C
Mon
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26.7°C
Tue
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26.7°C

How to Reserve Your Windward Side 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 Side Vacation Rental FAQs

What are the top vacation rentals in Windward Side?
How many vacation rentals have private pools in Windward Side?

There are 3 vacation rentals with private pools near Windward Side. Top-rated homes that have access to a swimming pool include:

Which vacation homes in Windward Side are best for families?

If you are looking for a family-friendly vacation home in Windward Side, 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 Side:

How many vacation rentals are available in Windward Side?

Currently, the total number of properties listed in 2026 is over 58 in the Windward Side area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windward Side.