- USA
- Florida
- Windley Key
- Villa
Discover Your Ideal Windley Key, Florida Villas for a Comfortable Stay
Discover Your Perfect Windley Key Villa
-
Rentals by Owner
-
Luxury Vacation Rentals
-
Pet Friendly Vacation Rentals
-
Unique Vacation Rentals
-
Cabin Rentals
-
Cottage Rentals
-
Ski Chalet Rentals
-
Timeshares
-
Villa Rentals
-
Hotels with Suites
-
Resort Rentals
-
Family Vacation Rentals
-
Vacation Rentals with Pools
-
Oceanfront Vacation Rentals
-
Beach House Rentals
-
Summer Vacation Rentals
-
Winter Vacation Rentals
-
Short Term Rentals
-
Corporate Accommodation
-
Large Group Vacation Rentals
-
Sustainable Travel
Windley Key Villa
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
Why Choose Rent By Owner for your Windley Key Villa?
What makes our Villa special?
Popular Areas for Windley Key Villa
Where are the best neighborhoods to stay in Windley Key?
In Windley Key, Florida, you’ll find neighborhoods that offer a peaceful escape with easy access to the natural beauty of the region. Whether you prefer staying near the waterfront or in more secluded areas, each neighborhood provides a unique ambiance perfect for your getaway. Explore the local surroundings and discover the ideal setting for your next stay in this vibrant part of Florida.
Venetian Shores
This area offers a tranquil setting with waterfront views ideal for relaxing getaways. You'll find it convenient to explore the region's natural beauty and enjoy the serene ambiance here.
View 45+ Rentals in Venetian ShoresBest Times to Visit Windley Key
When should you plan your Villa stay?
Choosing the right time to vacation here can enhance your experience, as the best seasons in Windley Key, Florida, USA, often align with pleasant weather and local events that make this destination truly enjoyable.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination experiences high demand as visitors seek to escape colder climates, making it an excellent time to secure a villa for your stay.
Spring (March to May)
Spring draws many travelers with pleasant weather and blooming scenery, offering ideal conditions for enjoying a villa here during your vacation.
Off-Season Highlights
Summer (June to August)
The summer season tends to be less crowded, providing a more relaxed atmosphere for booking a villa and exploring the region at your own pace.
Fall (September to November)
Autumn offers cooler temperatures and fewer visitors, making it an ideal time to enjoy your villa while experiencing the area's natural beauty without the peak-season crowds.
Weekly Weather Forecast for Windley Key
How to Book Your Windley Key Villa
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Windley Key
Common Villa Amenities
What amenities can you expect?
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
- Enjoy outdoor swimming pools available at many villas in this destination, perfect for relaxing under the sun.
- Take advantage of spacious patios or decks that offer a great spot for outdoor dining and entertaining.
- Benefit from lush gardens or landscaped yards that provide private outdoor spaces for leisure and play.
- Make use of barbecue grills or outdoor kitchens to enhance your al fresco meals while enjoying the warm climate.
- Explore nearby tranquil walking or biking paths that are accessible directly from select properties.
- Relax in hammocks or lounge chairs set up in your outdoor space, ideal for soaking up the sunshine.
- Utilize shared outdoor amenities such as tennis courts or volleyball areas often found within resort-style villa communities here.
Top Attractions Around Windley Key
What attractions are nearby?
In this vibrant region, you can enjoy a variety of activities nearby, including exploring marine attractions, participating in water sports, or relaxing on beautiful beaches, making it an ideal destination for those seeking adventure and leisure close to your accommodations.
Family Activities
- Coral Castle Museum: Explore this unique attraction where your family can marvel at intricate sculptures and learn about the fascinating history behind this regional landmark.
- John Pennekamp Coral Reef State Park: Spend a day discovering vibrant marine life through snorkeling or glass-bottom boat tours in this popular destination for outdoor adventures.
- Everglades National Park: Experience an exciting airboat tour to see diverse wildlife and enjoy the natural beauty that makes this park a top outdoor activity spot in the region.
- Key Largo Community Park: Enjoy family-friendly amenities like playgrounds, picnic areas, and walking trails perfect for relaxed afternoons in this scenic park nearby your stay.
Adult Activities
- Snorkeling and Diving: Explore the vibrant underwater world just off the coast, where you can enjoy snorkeling and diving experiences in the clear waters of the region.
- Fishing Charters: Embark on a fishing adventure tailored to your preferences, with local charters offering deep-sea and reef fishing experiences.
- Kayaking and Paddleboarding: Discover the scenic waterways and mangroves by renting kayaks or paddleboards, immersing yourself in the area's natural beauty.
- Eco Tours and Nature Walks: Join guided eco tours to explore the region’s unique ecosystems and observe local wildlife in their natural habitats.
Other Places to Stay in Windley Key, FL
Windley Key Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities in Advance: Take some time to research local leisure options and outdoor adventures to maximize your experience here, ensuring you make the most of your stay in this vibrant destination.
- Choose a Prime Location: When selecting your accommodation, opt for a property close to key attractions and conveniences to enjoy effortless access and more quality time during your visit.
- Explore Local Dining Options: Discover the area's culinary scene by visiting nearby restaurants and cafes-this allows you to indulge in authentic flavors while minimizing travel time.
- Take Advantage of Water-Based Activities: Given the region's beautiful waterways, engaging in boating or fishing can enhance your trip and provide memorable experiences right from your villa doorstep.
Transportation Options
- Rental Car Services: Major rental companies operate here, offering convenient access to explore the area and its scenic surroundings at your own pace.
- Public Transit: Local buses provide an affordable and reliable way to get around, connecting you easily to key destinations within this region.
- Private Taxi and Ride-Sharing: Popular ride-sharing apps and taxi services are readily available, ensuring comfortable transportation for short trips or airport transfers.
- Airport Shuttles: Transportation services from nearby airports simplify your arrival and departure, making your stay seamless from start to finish.
Local Customs Options
- Respect for Marine Life: When exploring the waters around this destination, it’s customary to observe local guidelines to protect the vibrant marine ecosystems.
- Celebration of Local Festivals: Participating in regional festivals is a cherished tradition that reflects the area's rich cultural heritage and community spirit.
- Casual Dress Code: Visitors typically adopt a relaxed style suitable for the warm climate, especially when attending local gatherings or dining out.
- Environmental Preservation: There is a strong emphasis on eco-friendly practices, encouraging guests to minimize their environmental impact while enjoying their stay here.
Frequently Asked Questions About Windley Key Rental Villas
1. What are the top Villas 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 Villas in Windley Key:
- Isla Mamey: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
- Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
- The Villa by the Bay, Islamorada FL private plunge pool, boat dockage & sunsets
- Island Time: Ocean Front, Ensuite bedrooms, Dock, Htd Pool
- Exec Bay T8 - 3 bedrooms
- Stunning Oceanfront Villa, Luxe Resort Perks at the Islands of Islamorada Resort
- Oceanview Villa at The Islands of Islamorada: Tropical Bliss & Resort Amenities
- Stunning Accessible Oceanfront Villa, Luxe Perks at The Islands of Islamorada
- LAST WEEK FOR SUPER DISCOUNTED RATE! BOOK NOW! Island Life Awaits you
- Isla Sands Collection: Sleeps 24, All Ensuite Bedrooms, Waterfront
2. How many Villas are available in Windley Key?
Currently, the total number of properties listed by RBO in 2026 is over 36 in the Windley Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Villas in Windley Key.
3. What is the cancellation policy for villas in Windley Key, Florida?
4. Are there any specific requirements or restrictions when booking a villa in this area?
5. How do I know if the villa has the amenities I need during my stay?
6. Is it possible to modify or extend my villa reservation after booking?
7. What should I do in case of an emergency or issue during my stay?
More Rentals You May Like Near Windley Key
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
