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Discover Your Perfect Windley Key Rentals by Owner

Windley Key Rentals by Owner

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8.7 (1439 Reviews)
Resort
Islander Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
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More Top-Rated Rentals by Owner in Windley Key Area

Why Choose Rent By Owner for your Windley Key vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Windley Key Rentals by Owner

Where are the best neighborhoods to stay in Windley Key?

Discover the ideal neighborhoods to stay in Windley Key, Florida, USA, by choosing a rental that suits your preferences. This area offers a variety of charming communities where you can enjoy a comfortable and convenient visit. Whether you prefer a peaceful retreat or a lively environment, the neighborhoods in Windley Key provide options that cater to different tastes. Booking through Rent By Owner ensures a reliable and seamless experience, helping you find the perfect home base for exploring this beautiful part of Florida. Experience the best of Windley Key by selecting a neighborhood that aligns with your travel needs.

Venetian Shores

In Venetian Shores, you can enjoy a peaceful waterside setting that offers easy access to the region's natural beauty. This neighborhood provides a convenient base for exploring the area while enjoying the comfort of privately-owned rentals tailored for a relaxing stay.

View 47+ Rentals in Venetian Shores

Venetian Shores

Here, you'll find a charming community that combines tranquil surroundings with proximity to key attractions, making it an ideal location for your Florida getaway. Booking a rental by owner in this area ensures a seamless experience, blending local hospitality with personalized accommodations.

View 47+ Rentals in Venetian Shores

Best Times to Visit Windley Key

When should you plan your Rentals by Owner stay?

Choosing the right time to vacation here can enhance your experience, so consider visiting during the region’s optimal seasons when the weather is most favorable for exploring and relaxing in this destination.

Peak Season Highlights

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Winter (December to February)

During winter, this destination experiences its peak travel period, attracting visitors seeking warm weather and clear skies. Booking your rental here early ensures you secure the best options during this busy season.

Average Temperature Daytime: 75°F - Nighttime: 65°F
spring
Spring (March to May)

Springtime brings a surge of visitors eager to enjoy pleasant temperatures and vibrant scenery in the area. Planning your stay in advance allows for a wider selection of rentals on Rent By Owner.

Average Temperature Daytime: 80°F - Nighttime: 70°F

Off-Season Highlights

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Summer (June to August)

The summer months see a dip in visitor numbers, making it an ideal time to find more affordable and flexible rental options while enjoying the region’s warmest weather.

Average Temperature Daytime: 85°F - Nighttime: 75°F
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Fall (September to November)

Autumn is a quieter season here, offering a relaxed atmosphere perfect for those looking to avoid crowds. This period provides excellent opportunities for booking privately-owned rentals at competitive rates.

Average Temperature Daytime: 78°F - Nighttime: 68°F

Weekly Weather Forecast for Windley Key

How to Book Your Windley Key vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Windley Key

More Top-Rated Rentals by Owner in Windley Key Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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

Outdoor Amenities

  • Access to private or community swimming pools for relaxation and leisure.
  • Outdoor grilling areas or barbecue setups for enjoying meals al fresco.
  • Spacious patios or decks ideal for outdoor dining or lounging in the sun.
  • Well-maintained gardens or landscaped yards to enhance your outdoor experience.
  • Parking spaces with ample room for vehicles, often including shaded or covered options.
  • Features like outdoor showers or wash stations for convenience during beach days or outdoor activities.
  • Proximity to scenic walking or biking paths that allow you to explore the area's natural beauty safely and comfortably.

Top Attractions Around Windley Key

What attractions are nearby?

Within this vibrant destination, you can enjoy a variety of outdoor activities, water sports, and scenic excursions that showcase the natural beauty of the region, making your stay truly memorable.

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Family Activities

  • Florida Keys Marine Sanctuary: Explore this family-friendly marine sanctuary to enjoy educational exhibits and interactive displays about the region's diverse underwater ecosystems.
  • John Pennekamp Coral Reef State Park: Experience snorkeling or glass-bottom boat tours nearby, where you can discover vibrant coral reefs and colorful marine life in this renowned Florida Keys attraction.
  • Windley Key Fossil Reef Geological State Park: Discover the area's geological history through guided tours and self-guided walks that highlight unique fossilized reef formations.
  • Local Beaches and Parks: Relax and have fun at the many nearby beaches and parks, perfect for picnics, swimming, and family outings within this scenic part of the Florida Keys region.
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Adult Activities

  • Snorkeling and Diving Tours: Explore the vibrant underwater world just off the coast, where you can discover coral reefs and marine life representative of this region's aquatic beauty.
  • Fishing Excursions: Spend a day on the water enjoying guided fishing trips that take you through prime fishing spots, showcasing the area's rich aquatic biodiversity.
  • Kayaking Adventures: Paddle along scenic waterways and mangroves, providing a peaceful way to experience the natural scenery unique to this destination.
  • Wildlife Watching Tours: Join guided tours to observe local bird species and other wildlife habitats that thrive in the region's coastal environment.

Other Places to Stay in Windley Key, FL

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Windley Key Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: Take the time to research local attractions and outdoor activities to maximize your stay here, ensuring you experience the best the area has to offer.
  • Select a Prime Rental Location: Choose accommodations close to popular spots or scenic areas for easy access and more enjoyable exploration of this destination.
  • Respect the Neighborhood and Environment: Practice eco-friendly habits and be mindful of community guidelines to help preserve the natural beauty and tranquility of the region.
  • Check Amenities and Conveniences: Verify that your rental provides essential amenities to make your visit comfortable, allowing you to relax and unwind during your time here.

Transportation Options

  • Rental Car Services: Convenient options like major car rental agencies allow you to explore the region at your own pace, making day trips and sightseeing around Windley Key effortless.
  • Taxis and Ride-Sharing: Reliable taxi services and ride-sharing apps offer quick transportation within the area, ensuring you can easily reach local attractions or your vacation rental.
  • Public Transit: Local bus systems provide an economical way to travel throughout the region, connecting you to key points of interest near your Windley Key accommodation.
  • Boat Rentals and Water Taxis: Given its coastal location, renting a boat or taking a water taxi grants you scenic access to nearby islands and waterfront destinations here in the region.

Local Customs Options

  • Respect for Marine Conservation: You should be mindful of the region's delicate marine environment and adhere to local guidelines when engaging in water activities or visiting coastal areas.
  • Celebration of Local Festivals: Participating in regional festivals is a great way to experience authentic traditions, as they often feature unique customs specific to this area’s cultural heritage.
  • Casual Dress Code: When exploring here, dressing comfortably and appropriately for warm weather and outdoor activities is customary and appreciated by locals.
  • Environmental Responsibility: It's important to follow eco-friendly practices, such as proper waste disposal and conservation efforts, to help preserve the area's natural beauty for visitors like you.

Frequently Asked Questions About Windley Key Rentals by Owner

1. What are the top vacation rentals in Windley Key?

There are a lot of options in Windley Key. If you plan on staying in the Windley Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windley Key:

2. How many Rentbyowner vacation rentals are available in Windley Key?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 631 in the Windley Key area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windley Key. 

3. What is the cancellation policy for rental properties in this area?

Cancellation policies vary by individual owner and listing. To understand the specific terms, please review the cancellation details provided on the property listing or contact the owner directly before booking.

4. How do I know if the rental has all the amenities I need?

Each rental listing includes a detailed list of amenities. For confirmation on specific features, such as Wi-Fi, kitchen appliances, or laundry facilities, review the listing information carefully or reach out to the owner with your questions.

5. Are there any additional fees or charges I should be aware of when booking?

Additional fees, such as cleaning fees or security deposits, are specified within each listing. To avoid surprises, read the full fee breakdown on the property page or discuss any concerns directly with the owner prior to booking.

6. What is the process for checking in and checking out of the rental?

Check-in and check-out procedures are outlined in the listing details. Many owners provide flexible options; however, it's best to confirm the specific times and methods directly with the property owner before your arrival.

7. Is there a minimum stay requirement for rentals here?

Minimum stay requirements vary depending on the property. These details are included in the listing description. If you have special scheduling needs, contact the owner to see if accommodations can be made.

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More Top-Rated Rentals by Owner in Windley Key Area