Discover Your Perfect Windsor Woods Rentals by Owner

Windsor Woods Rentals by Owner

More Top-Rated Rentals by Owner in Windsor Woods Area

Why Choose Rent By Owner for your Windsor Woods vacation rental?

What makes our Rentals by Owner special?

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

Popular Areas for Windsor Woods Rentals by Owner

Where are the best neighborhoods to stay in Windsor Woods?

Windsor Woods in Clearwater, Florida offers a variety of appealing neighborhoods that make for an ideal stay. If you are seeking a quiet, residential area with convenient access to local amenities, Windsor Woods provides a welcoming environment perfect for relaxation. For those wanting proximity to the vibrant entertainment and beautiful beaches of Clearwater, choosing accommodations within or near this neighborhood ensures that you are well-positioned to enjoy all the region has to offer. Whether you prefer a peaceful retreat or easy access to outdoor activities, booking through Rent By Owner in Windsor Woods allows you to experience Clearwater’s charm with confidence and ease.

Windsor Park

Located within the region's scenic surroundings, Windsor Park offers a quiet and convenient base for your stay in Clearwater. Here, you'll find comfortable rental options that provide easy access to the area's best attractions and beaches.

View 1112+ Rentals in Windsor Park

Best Times to Visit Windsor Woods

When should you plan your Rentals by Owner stay?

Knowing the best time to visit here can help you enjoy the area’s warm climate and pleasant surroundings, making your rental by owner experience in Windsor Woods, Clearwater, Florida, USA truly memorable.

Peak Season Highlights

spring
Spring (March to May)

During the spring months, you can enjoy pleasant weather and blooming scenery, making it an ideal time to explore this destination.

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

The winter season offers mild temperatures and less crowded accommodations, providing a more relaxed visit to the region.

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

Off-Season Highlights

image
Summer (June to August)

In summer, expect hotter weather and the region’s peak tourist activity, which may impact the tranquility of your stay.

Average Temperature Daytime: 85°F - 92°F - Nighttime: 70°F - 75°F
image
Fall (September to November)

Autumn brings cooler temperatures and fewer visitors, creating a cozy atmosphere for your stay at this popular Florida destination.

Average Temperature Daytime: 75°F - 85°F - Nighttime: 55°F - 65°F

Weekly Weather Forecast for Windsor Woods

How to Book Your Windsor Woods 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 Windsor Woods

More Top-Rated Rentals by Owner in Windsor Woods 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

  • Enjoy a private outdoor pool to relax and cool off during your stay.
  • Take advantage of a spacious, furnished patio for outdoor dining and entertaining.
  • Benefit from lush, landscaped gardens that create a serene outdoor environment.
  • Make use of outdoor grilling facilities for delicious barbecues with family and friends.
  • Relax in a screened-in porch that offers comfortable space to unwind outdoors.
  • Discover nearby outdoor sports amenities such as tennis courts or walking trails, perfect for active vacations.
  • Utilize ample parking space in the driveway or garage for convenience and security.

Top Attractions Around Windsor Woods

What attractions are nearby?

Within this vibrant area, you can enjoy easy access to beautiful beaches, scenic parks, and outdoor activities that make your stay in Windsor Woods truly memorable.

image
image

Family Activities

  • Windsor Woods Community Park: Enjoy a family picnic or outdoor playtime at this nearby park offering open green spaces and playgrounds suitable for children of all ages.
  • Clearwater Marine Aquarium: Visit this renowned aquarium to experience engaging marine life exhibits and interactive opportunities perfect for a memorable family day out.
  • Beach Day at Clearwater Beach: Spend quality time building sandcastles and splashing in the Gulf of Mexico just moments from here, making it an ideal spot for family fun in the sun.
  • Museum of Nature and Science: Explore this educational attraction that provides hands-on exhibits and interactive displays designed to inspire curiosity in young minds visiting the region.
image

Adult Activities

  • Visit Clearwater Marine Aquarium: Discover marine life conservation efforts and enjoy inspiring aquatic exhibits right in the region.
  • Explore local golf courses: Tee off at nearby championship golf courses that offer scenic views and challenging play for golf enthusiasts visiting here.
  • Enjoy Nature Parks: Spend a relaxing day at parks with walking trails, picnic areas, and opportunities for wildlife viewing in the area.
  • Experience Water Sports: Engage in kayaking, paddleboarding, or boating on the pristine waters, perfect for outdoor adventure seekers in this destination.

Windsor Woods Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Attractions: Research nearby parks and recreational spots to enhance your experience in this popular coastal region.
  • Utilize Rent By Owner Listings: Choose rental properties that offer prime locations and amenities tailored to your needs here for a more comfortable stay.
  • Explore the Area's Natural Beauty: Take advantage of the region’s beaches and outdoor spaces to relax and enjoy the scenic surroundings during your visit.
  • Connect with Local Services: Take advantage of trusted local vendors and service providers recommended within this community for a seamless trip.

Transportation Options

  • Personal Vehicle: Exploring the area with your own car offers convenient access to local attractions and amenities in Windsor Woods, Clearwater, Florida.
  • Local Bus Service: Public transportation options are available nearby, providing an economical way to navigate around this part of Clearwater.
  • Taxi and Rideshare Services: Reliable taxi companies and rideshare apps like Uber and Lyft operate in the region, making short trips around the destination seamless.
  • Bicycle Rentals: For a more active experience, renting a bicycle allows you to enjoy the scenic streets of the area at your own pace.

Local Customs Options

  • Respect for Coastal Conservation: Locals here take pride in preserving the area's natural beauty, so you'll notice a community commitment to environmental sustainability.
  • Beach Etiquette: Visitors are encouraged to follow the unspoken rules of the beach, such as keeping noise levels down and disposing of trash properly, which helps maintain the area's serene atmosphere.
  • Local Dining Customs: Sharing meals with fresh seafood is a common tradition, reflecting the region's rich maritime heritage and welcoming atmosphere.
  • Community Events and Festivals: Participating in seasonal celebrations and local festivals offers a glimpse into the area's vibrant culture and friendly spirit.

Frequently Asked Questions About Windsor Woods Rentals by Owner

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 Rentbyowner vacation rentals are available in Windsor Woods?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 978 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. 

3. What is the cancellation policy for rentals by owner in Windsor Woods, Clearwater?

Cancellation policies vary depending on the individual rental listing. To ensure clarity, review the specific cancellation terms provided in the listing details or contact the property owner directly before booking.

4. How do I confirm booking availability and secure my stay in this region?

Availability can be checked through the listing on Rent By Owner. Once you select your dates, follow the reservation process to secure your booking, and contact the owner if you have any special requests or need further confirmation.

5. Are there any additional fees I should be aware of when booking a rental by owner in this area?

Additional fees such as cleaning fees, security deposits, or service charges are typically detailed on the listing page. Review these details carefully before completing your reservation, or reach out to the owner for clarification.

6. What amenities are generally included in rentals by owner in this destination?

Most rentals offer essential amenities to ensure a comfortable stay, but specifics like Wi-Fi, parking, or kitchen facilities vary by listing. Check the property description or contact the owner for detailed information about what’s included.

7. How do I inquire about special requirements or questions before booking?

You can contact the property owner directly through the messaging feature on Rent By Owner. This allows you to discuss any special needs, ask questions about the property, or clarify booking details prior to finalizing your reservation.

More Rentals You May Like Near Windsor Woods

More Top-Rated Rentals by Owner in Windsor Woods Area