Discover Your Perfect Windsor Woods Vacation Homes

Best Vacation Homes in Windsor Woods

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Windsor Woods Luxury Rentals

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Windsor Woods Pet Friendly Vacation Rentals

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Windsor Woods Large Vacation Homes

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Why Choose Rent By Owner for your Windsor Woods 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.

Popular Areas for Windsor Woods Vacation Rentals

Where are the best neighborhoods to stay in Windsor Woods?

Windsor Woods in Clearwater, Florida offers a peaceful and family-friendly neighborhood ideal for your next vacation stay. Located conveniently near the Gulf Coast, this area provides easy access to beautiful beaches and local attractions, making it a top choice for travelers seeking both relaxation and convenience. Choosing to stay in Windsor Woods ensures you experience a comfortable and welcoming environment, perfect for creating lasting memories during your visit to Clearwater.

Windsor Park

In this peaceful neighborhood, you can enjoy convenient access to the pristine beaches and vibrant local amenities that make Clearwater a popular destination. Here, your choice of vacation rentals offers a comfortable retreat close to the region’s most sought-after attractions.

View 1112+ Rentals in Windsor Park

Clearwater

This lively coastal city provides an ideal setting for relaxing on sandy shores and exploring picturesque waterfront views. Staying here ensures you are near top-rated beaches and entertainment options, making your visit both enjoyable and memorable.

View 1033+ Rentals in Clearwater

Best Times to Visit Windsor Woods

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here ensures you can fully enjoy the relaxing atmosphere and pleasant weather that this destination offers year-round.

Peak Season Highlights

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Spring (March to May)

During the spring months, you'll enjoy warm weather and abundant sunshine, making it an ideal time to explore this destination in comfort.

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

The winter season offers pleasant temperatures and a lively atmosphere, perfect for those seeking a mild winter escape in the area.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Summer (June to August)

While summer tends to be hot and humid, this period can be quieter, providing more relaxed access to local amenities and opportunities for outdoor activities.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 70°F to 75°F
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Fall (September to November)

In fall, the region experiences milder weather with fewer tourists, making it a good choice for travelers looking for budget-friendly options and peaceful surroundings.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F

Weekly Weather Forecast for Windsor Woods

How to Book Your Windsor Woods 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 Windsor Woods

More Top-Rated Vacation Rentals in Windsor Woods 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 outdoor pool to relax and cool off during your stay in the region.
  • Take advantage of well-maintained outdoor grilling areas for tasty meals with family and friends.
  • Make the most of spacious patios or balconies perfect for soaking up the sunny Florida weather.
  • Experience direct access to lush landscaped gardens or yards ideal for outdoor activities.
  • Utilize dedicated parking spaces within the property’s outdoor area for convenience.
  • Benefit from convenient outdoor shower facilities to rinse off after beach visits.
  • Explore nearby walking trails or scenic outdoor paths that showcase the area's natural beauty.

Top Attractions Around Windsor Woods

What attractions are nearby?

Nearby, you can enjoy a variety of outdoor activities, local parks, and scenic spots that showcase the natural beauty of the region, providing an ideal setting for relaxation and exploration during your stay.

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Family Activities

  • Clearwater Marine Aquarium: Discover the magic of marine life and enjoy interactive exhibits at this family-friendly aquarium, perfect for a day of educational fun in the area.
  • Beach Day at Clearwater Beach: Relax on the pristine sands and splash along the shoreline at one of Florida's most popular beaches, ideal for memorable family outings.
  • Captain Memo’s Pirate Cruise: Embark on an exciting pirate-themed boat adventure suitable for children and adults alike, offering engaging entertainment right here near your stay.
  • Heritage Village Museum: Step back in time and explore historical buildings and exhibits that provide insight into the region’s rich cultural history, great for young explorers.
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Adult Activities

  • Golfing at Clearwater Golf Course: Experience a leisurely round of golf on well-maintained fairways that showcase the region’s scenic beauty just minutes from your accommodation.
  • Exploring local breweries and wine bars: Savor craft beverages and learn about the area's vibrant brewing scene at popular spots within easy reach here.
  • Visiting the Clearwater Marine Aquarium: Discover the region’s commitment to marine life conservation while enjoying engaging exhibits and interactive encounters.
  • Shopping along the Westfield Countryside Mall: Take advantage of the area's retail therapy with a variety of shops, boutiques, and dining options to explore during your stay.

Windsor Woods Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Beaches: Take advantage of the nearby beaches to enjoy sunbathing, swimming, and water sports that showcase the natural beauty of this coastal destination.
  • Plan Outdoor Activities: Discover outdoor recreational options like parks and nature trails around the area to make the most of the region’s scenic landscapes.
  • Visit Local Dining Spots: Savor fresh seafood and regional cuisine at local eateries to fully immerse yourself in the culinary offerings here.
  • Utilize Transportation Options: Use convenient local transportation services or rental bikes to easily explore the region and access popular attractions.

Transportation Options

  • Personal Vehicles: Renting a car provides the flexibility to explore all that this area has to offer at your own pace, making it an ideal transportation option for visitors staying in vacation rentals nearby.
  • Local Taxis and Ride-Sharing Services: Taxis and ride-sharing apps like Uber and Lyft offer convenient, door-to-door service around the region, perfect for quick trips from your rental accommodation.
  • Public Transit: The local bus systems operate throughout here, offering an affordable and reliable means of transportation for getting to popular spots within the area.
  • Bicycle Rentals: Biking is a popular way to navigate the scenic streets of this destination, with bike rental services readily available for eco-friendly and leisurely excursions.

Local Customs Options

  • Locally Celebrated Festivals: You can experience vibrant festivals that showcase the community spirit and traditions unique to this region near Windsor Woods.
  • Southern Hospitality: Visitors often notice the warm and welcoming attitude of residents, reflecting the area's friendly and relaxed atmosphere.
  • Fresh Seafood Cuisine: Enjoying fresh, locally caught seafood is a cherished custom here, highlighting the region’s close ties to the Gulf Coast.
  • Community Events and Markets: Participating in outdoor markets and local gatherings offers insight into the area's rich cultural heritage and social customs.

Frequently Asked Questions About Windsor Woods?

1. What are the top vacation rentals in Windsor Woods?

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

2. How many vacation rentals have private pools in Windsor Woods?

There are 141 vacation rentals with private pools near Windsor Woods. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Windsor Woods are best for families?

If you are looking for a family-friendly vacation home in Windsor Woods, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor Woods:

4. How many Rentbyowner vacation rentals are available in Windsor Woods?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1192 in the Windsor Woods 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 Windsor Woods. 

5. What is the cancellation policy for vacation rentals in Windsor Woods, Clearwater?

Cancellation policies vary depending on the property owner. To understand the specific terms and any potential fees, please review the listing details or contact the host directly before completing your reservation.

6. How do I know if the vacation rental has amenities suitable for my needs in this area?

Each property listing provides detailed information about available amenities. Be sure to check the description and photos, and reach out to the owner if you have special requirements or need clarification.

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

Additional fees such as cleaning charges, service fees, or local taxes are typically outlined in the booking details. Review the total cost breakdown carefully or communicate with the host for precise fee information.

8. What is the check-in and check-out process for vacation rentals in this destination?

The check-in and check-out procedures are specified in each listing. Some rentals offer flexible timings, while others follow strict schedules. Confirm these details with the owner prior to your arrival to ensure a smooth stay.

9. How can I confirm the safety measures and cleanliness standards of a vacation rental in the region?

Listings often include information about cleaning protocols and safety features. For additional assurance, contact the property owner directly to inquire about their health and safety practices, especially if you have specific concerns.

Windsor Woods Top Rated Vacation Rentals

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