Discover Your Perfect Windward Cay Vacation Homes

Why Choose Rent By Owner for your Windward Cay Vacation Rental Homes?

What makes our Vacation Rentals 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.

Best Times to Visit Windward Cay

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can greatly enhance your experience, as the region offers ideal conditions for a relaxing getaway during certain seasons when you can enjoy pleasant weather and fewer crowds.

Peak Season Highlights

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Spring (March to May)

During spring, you'll experience warm and inviting weather, ideal for enjoying the region's outdoor activities and exploring local attractions.

Average Temperature Daytime: 75°F - 85°F - Nighttime: 55°F - 65°F
winter
Winter Holidays (December to February)

The winter holiday months bring cooler temperatures and festive atmosphere, making it a perfect time for those looking to escape colder climates while enjoying pleasant weather here.

Average Temperature Daytime: 65°F - 75°F - Nighttime: 45°F - 55°F

Off-Season Highlights

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Summer (June to August)

Experience the hottest weather of the year with longer daylight hours, which provide excellent conditions for outdoor pursuits in this popular destination.

Average Temperature Daytime: 85°F - 95°F - Nighttime: 70°F - 75°F
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Fall (September to November)

As the region transitions into fall, you’ll find milder temperatures and fewer crowds, offering a more relaxed environment to enjoy your stay.

Average Temperature Daytime: 70°F - 80°F - Nighttime: 50°F - 60°F

Weekly Weather Forecast for Windward Cay

How to Book Your Windward Cay Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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 Windward Cay

More Top-Rated Vacation Rentals in Windward Cay Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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

  • Enjoy a private swimming pool where you can relax and unwind outdoors.
  • Take advantage of a spacious patio area perfect for outdoor dining or entertaining friends.
  • Benefit from well-maintained landscaped gardens that enhance the scenic surroundings.
  • Make use of outdoor seating areas to soak up the sun and enjoy the pleasant climate.
  • Access nearby walking trails or green spaces for outdoor activities and exploration.
  • Relax in a screened lanai, ideal for enjoying the fresh air without insects.
  • Utilize outdoor lighting features to extend your time outdoors during the evening hours.

Top Attractions Around Windward Cay

What attractions are nearby?

Within this vibrant region, you can enjoy a variety of nearby activities such as exploring local parks, engaging in water sports, or experiencing family-friendly entertainment options that make your stay here truly memorable.

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Family Activities

  • Visit Shingle Creek Regional Park: Enjoy a family picnic or explore scenic trails along the water in this beautiful regional park nearby, perfect for outdoor adventures.
  • Explore the Osceola County Historical Society:** Discover local history and culture through engaging exhibits that will entertain and educate children of all ages.
  • Experience Fun Spot America Kissimmee: Spend an exciting day at this amusement park offering rides, arcade games, and attractions suited for the entire family.
  • Relax at Lake Cecile Park: Take a break with a leisurely stroll or a family fishing session at this tranquil lakeside park, ideal for unwinding during your stay here.
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Adult Activities

  • Golfing at Mystic Dunes Resort & Golf Club: Enjoy a leisurely round of golf on the scenic courses that are just a short drive away, offering an ideal escape for enthusiasts seeking relaxation and sport in the area.
  • Exploring local dining options: Savor diverse culinary experiences at nearby restaurants, where you can indulge in Florida’s vibrant food scene after a day of adventures here.
  • Visit shopping centers and outlet malls: Take advantage of nearby retail outlets for a convenient shopping spree, making it easy to find souvenirs and essentials during your stay.
  • Participating in water sports: Engage in kayaking, paddleboarding, or boating along the area's calm lakes, perfect for adults looking to enjoy outdoor activities in this destination.

Windward Cay Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Amenities: Take advantage of nearby shopping, dining, and entertainment options to enhance your stay in this popular destination.
  • Plan Early for Attractions: Book tickets or arrange tours in advance to avoid missing out on the region's most sought-after experiences.
  • Utilize Water Access Points: Make the most of the area’s lakes and waterways for relaxing boat rides or fishing days during your visit.
  • Stay Connected with Local Tips: Engage with local guides or hosts to discover hidden gems and insider advice for a memorable experience here.

Transportation Options

  • Personal Vehicle: Having your own car provides the most flexibility for exploring the region around Windward Cay and accessing nearby attractions with ease.
  • Shuttle Services: Convenient shuttle options are available in this area, offering reliable transportation to major theme parks and local points of interest.
  • Taxi and Rideshare: Taxis and rideshare services like Uber and Lyft are readily accessible for quick, hassle-free trips within the region.
  • Public Transportation: While limited, some local bus routes connect here to key destinations, providing an affordable transportation alternative for visitors.

Local Customs Options

  • Respect for Quiet Hours: Maintaining quiet after certain hours is appreciated here, as the community values peaceful evenings for all residents and visitors alike.
  • Local Greeting Etiquette: When interacting with neighbors or local staff, a friendly greeting is customary and helps foster a welcoming atmosphere in the area.
  • Environmental Respect: Proper disposal of trash and recycling is important to keep the region’s natural beauty intact and ensure a clean environment for everyone.
  • Community Rules Compliance: Adhering to posted guidelines regarding pool usage and communal facilities ensures a safe and enjoyable experience for all guests in your vacation stay.

Frequently Asked Questions About Windward Cay?

1. What are the top vacation rentals in Windward Cay?

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

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

There are 6534 vacation rentals with private pools near Windward Cay. Top-rated RBO homes that have access to a swimming pool include:

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

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

4. How many Rentbyowner vacation rentals are available in Windward Cay?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 14553 in the Windward Cay 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 Windward Cay. 

5. What is the cancellation policy for booking a vacation rental here?

The cancellation policy varies depending on the individual listing. You should review the specific property's cancellation terms directly on the listing page or contact the owner for detailed information before completing your reservation.

6. How do I secure my reservation at a vacation rental in this area?

Reservations are confirmed once you complete the booking process and any required deposits are paid through the platform. For added assurance, communicate with the property owner if you have special requests or need confirmation of availability.

7. Are there any additional fees I should be aware of when booking a vacation rental?

Additional charges such as cleaning fees, service fees, or taxes are often included in the total price displayed at checkout. Always review the detailed pricing information on the listing to understand all potential costs.

8. What amenities are typically included in vacation rentals in this destination?

Amenities offered can vary by property, but most include essentials like Wi-Fi, a fully equipped kitchen, and parking. Check the individual listing for a comprehensive list of amenities provided at each home.

9. How can I contact the property owner if I have questions before booking?

You can reach out directly to the property owner through the contact options provided on the listing page. This ensures you get accurate information about the rental and can clarify any specific requirements or concerns.

Windward Cay Top Rated Vacation Rentals

See More Windward Cay Vacation Rentals