Best Vacation Homes in Windley Key
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Windley Key Luxury Rentals
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Windley Key Pet Friendly Vacation Rentals
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Windley Key Large Vacation Homes
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Why Choose Rent By Owner for your Windley Key Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Windley Key Vacation Rentals
Where are the best neighborhoods to stay in Windley Key?
When selecting a neighborhood to stay in Windley Key, Florida, you’ll find that its charming surroundings offer the perfect backdrop for a relaxing getaway. This area provides convenient access to beautiful coastal views and a peaceful atmosphere, making it an ideal choice for those seeking tranquility. Whether you're looking for a cozy retreat or a lively spot close to local attractions, Windley Key's neighborhoods are designed to cater to your preferences. With a focus on comfort and ease, you'll enjoy a seamless booking experience for your vacation rentals, ensuring your trip is both enjoyable and memorable.
Venetian Shores
In Venetian Shores, you can enjoy a peaceful setting with convenient access to the water, making it an ideal choice for those seeking relaxing coastal experiences. Here, the tranquil atmosphere and scenic views provide the perfect backdrop for your stay in this part of Florida.
View 47+ Rentals in Venetian ShoresBest Times to Visit Windley Key
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit this destination can enhance your experience, as the region offers different weather and activity opportunities throughout the year, making it important to plan your stay accordingly when booking through trusted vacation rentals here.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination experiences its peak season, attracting visitors seeking mild weather and sunny days. It's an ideal time to enjoy outdoor activities and explore the region comfortably.
Spring Break (March to April)
Spring break brings a surge of travelers to the area, making it one of the busiest times of the year. Booking your vacation rentals early ensures you secure the best options for this lively period.
Off-Season Highlights
Summer (June to August)
The summer months see a dip in visitors, offering a quieter experience. It's a great opportunity to enjoy more peaceful surroundings and potentially better rates on your vacation rentals.
Fall (September to November)
Fall is a less busy season, providing a relaxed atmosphere with pleasant weather. This period is perfect for those looking to avoid crowds while still enjoying the region's natural beauty.
Weekly Weather Forecast for Windley Key
How to Book Your Windley Key Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Windley Key
Common Vacation Rentals 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 a private outdoor swimming pool to relax after exploring the area.
- Take advantage of well-maintained outdoor grilling areas for family cookouts.
- Relax on a spacious patio or deck with comfortable outdoor furniture.
- Benefit from lush, landscaped gardens that enhance your outdoor experience.
- Utilize dedicated parking spaces within a secure and convenient outdoor setting.
- Experience outdoor recreational facilities like tennis courts or playgrounds, if available.
- Walk or cycle along scenic pathways to explore the natural beauty of this destination.
Top Attractions Around Windley Key
What attractions are nearby?
Within this vibrant area, you can enjoy a variety of activities such as exploring local parks, engaging in water-based adventures, and discovering cultural attractions nearby, making your stay in Windley Key, Florida, an unforgettable experience.
Family Activities
- Snorkeling and Marine Exploration: Discover vibrant coral reefs and marine life just off the coast, offering an exciting underwater adventure for the whole family in this scenic area.
- Visit the Local Aquariums or Marine Parks: Enjoy interactive exhibits and educational displays that highlight the region's aquatic ecosystems, perfect for young explorers seeking fun and learning.
- Enjoy Water Sports and Beach Activities: Spend your days engaging in kayaking, paddleboarding, or building sandcastles along the shoreline of this popular destination.
- Wildlife Viewing and Nature Walks: Explore nearby nature trails where you can spot native wildlife and enjoy the lush scenery that characterizes the region’s natural beauty.
Adult Activities
- Snorkeling and Diving Tours: Explore the vibrant marine life just off the coast, as the region is renowned for its clear waters and accessible coral reefs perfect for underwater adventures.
- Fishing Charters: Spend a day on the water with local fishing charters that offer expert-guided trips, providing an excellent opportunity to experience the region’s rich aquatic ecosystem.
- Visit Local Museums and Cultural Centers: Discover the area's history and heritage through engaging exhibits and cultural displays at nearby museums and heritage sites.
- Dining at Waterfront Restaurants: Enjoy fresh seafood and regional cuisine at waterfront eateries that showcase the flavors of this coastal destination.
Other Places to Stay in Windley Key, FL
Windley Key Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Water Activities: Take advantage of the region’s calm waters by engaging in kayaking or paddleboarding right from your vacation rental doorstep.
- Plan Your Day Around Sunrise and Sunset: Witness breathtaking views by scheduling outdoor activities during the early morning or evening hours, highlighting this destination’s natural beauty.
- Utilize Nearby Nature Trails: Discover scenic trails close to your rental to enjoy peaceful walks or bike rides amidst lush surroundings.
- Make the Most of the Area’s Dining Options: Sample fresh seafood and authentic local cuisine at nearby eateries, enriching your stay with regional flavors.
Transportation Options
- Rental Car Services: You can easily explore the area with rental car services available nearby, providing flexibility to visit local attractions at your own pace.
- Taxi and Ride-Sharing Options: Convenient taxi and ride-sharing options are accessible here, making short trips around the region straightforward without the need for personal transportation.
- Public Transportation: Local buses provide an affordable way to get around, connecting you to key destinations within this destination’s transportation network.
- Airport Transfers: Reliable airport transfer services ensure smooth arrival and departure experiences from the nearby airports serving this region.
Local Customs Options
- Local Seafood Cuisine: You can indulge in fresh, locally caught seafood that is a staple here, reflecting the region’s rich maritime heritage.
- Marine Conservation Etiquette: Respect for the area's delicate coral reefs and marine life is common, with visitors encouraged to follow conservation guidelines during water activities.
- Celebration of Nautical Events: The community often hosts maritime festivals and boat parades, where participating in or observing these traditions provides a taste of the local culture.
- Respect for Indigenous Heritage: Visitors demonstrate reverence for Native American history through thoughtful engagement at local sites and acknowledgment of indigenous customs.
Frequently Asked Questions About Windley Key?
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:
- OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
- OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
- Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- Oceanside Getaway: Renovated Home with Boat Slip, Pool & Beach - Gated community
- The Caribbean Resort
- Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
- WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
- 5 bedroom - Deep Dockage & Heated Pool in Islamorada.
- Serenity by the Sea! Anglers Reef with Boat Slip Available!
- 4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
2. How many vacation rentals have private pools in Windley Key?
There are 118 vacation rentals with private pools near Windley Key. Top-rated RBO homes that have access to a swimming pool include:
- Private End Unit in Anglers Reef Resort Islamorada Boat Slip, Ocean Views & Pool
- Private Cottage on Bayfront Estate – Pool, Beach, and Boating Paradise
- Charming cottage on the Florida Bay in the heart of Islamorada with pool, dockage, beach + more
- SEASONAL WATERFRONT RENTAL in Venetian Shores, Islamorada, Pool & New Dock
3. Which vacation homes in Windley Key are best for families?
If you are looking for a family-friendly vacation home in Windley Key, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windley Key:
4. 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 752 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.
5. What is the cancellation policy for vacation rentals in Windley Key, Florida?
6. How do I find the best vacation rentals in Windley Key, Florida?
7. Are there any additional fees associated with booking a vacation rental in Windley Key?
8. What amenities are generally included in vacation rentals here?
9. How do I secure my booking at a vacation rental in Windley Key, Florida?
Windley Key Top Rated Vacation Rentals
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