Discover Your Perfect Windermere Vacation Homes

Windermere Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Windermere on PetFriendly.io

Why Choose Rent By Owner for your Windermere 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 Windermere

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you enjoy the region's charm at its best, whether you're seeking leisure during peak seasons or a quieter retreat in the off-peak months.

Peak Season Highlights

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Spring (March to May)

During spring, you can enjoy pleasant weather and blooming scenery, making it an ideal time to explore the region's outdoor activities while staying in comfortable vacation rentals.

Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
summer
Summer (June to August)

The summer months bring warm temperatures and longer days, perfect for outdoor adventures and relaxing stays in rental properties that offer a cool retreat from the heat.

Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F

Off-Season Highlights

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Fall (September to November)

Autumn offers cooler weather and vibrant foliage, providing a serene atmosphere for your stay at vacation rentals before the winter crowds arrive.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
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Winter (December to February)

Winter presents a quieter period with chilly temperatures, making it a peaceful time to reserve cozy accommodations and enjoy the tranquil surroundings.

Average Temperature Daytime: 30-45°F - Nighttime: 20-30°F

Weekly Weather Forecast for Windermere

How to Book Your Windermere 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 Windermere

More Top-Rated Vacation Rentals in Windermere 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 patio or deck perfect for relaxing and dining al fresco.
  • Take advantage of landscaped gardens or lush yard spaces to unwind amidst nature.
  • Make use of outdoor grilling facilities to host cookouts in the pleasant weather.
  • Benefit from a swimming pool or access to a community pool for refreshing dips during warm days.
  • Explore nearby walking trails or biking paths directly accessible from your rental.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
  • Find outdoor recreational amenities such as volleyball courts or playgrounds, ideal for family fun.

Top Attractions Around Windermere

What attractions are nearby?

While staying here, you'll find a variety of nearby activities to enjoy in the region, including outdoor recreation, local dining options, and family-friendly attractions that showcase the best of Windermere in Fishers, Indiana.

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Family Activities

  • Conner Prairie Interactive History Park: Engage your family in hands-on history exhibits and live reenactments at this educational attraction in Fishers.
  • The Children's Museum of Indianapolis: Discover a world of imagination and learning through interactive exhibits designed to entertain children of all ages within the region.
  • Flat Fork Creek Park: Enjoy outdoor activities such as hiking, picnicking, and playground fun in this scenic park near Windermere.
  • Fishers YMCA Family Fun Center: Take part in a variety of indoor attractions, including climbing walls and arcade games, perfect for family bonding here in Fishers.
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Adult Activities

  • Golfing at Ironwood Golf Course: Enjoy a relaxing day on the fairways at this popular golf course, offering scenic views and a challenging game in the region.
  • Exploring Conner Prairie Interactive History Park: Immerse yourself in local history with engaging exhibits and hands-on activities designed for adult visitors seeking cultural enrichment.
  • Shopping and Dining in Fishers’ Historic Downtown: Discover unique boutiques and savor gourmet cuisine at a variety of restaurants nestled in the area's vibrant downtown district.
  • Fishing and Boating on Geist Reservoir: Take advantage of the serene waters nearby for a day of fishing, kayaking, or enjoying a peaceful boat ride around the region.

Windermere Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take advantage of the area’s renowned parks and recreational spots to enjoy outdoor activities that showcase the region’s natural beauty.
  • Plan Your Dining Experience: Discover local eateries and cafes to experience regional flavors, making your stay more authentic and memorable.
  • Utilize Nearby Amenities: Make the most of community facilities such as shopping centers, fitness centers, and entertainment venues to enhance your visit.
  • Choose the Right Vacation Rental: Select a well-reviewed property here that offers convenient access to key destinations, ensuring a comfortable and hassle-free stay.

Transportation Options

  • Personal Vehicle: Renting or driving your own car provides the most flexibility to explore this destination and its surrounding attractions with ease.
  • Local Bus Services: Public bus routes in the area offer an affordable and convenient way to navigate around here without the need for private transportation.
  • Rideshare Services: Companies like Uber and Lyft operate within this region, providing quick, reliable transportation options when you prefer door-to-door service.
  • Shuttle Services: Airport shuttles and private transfer services are available for seamless arrivals and departures in the area, ensuring a stress-free travel experience.

Local Customs Options

  • Attending Local Festivals: Celebrating regional festivals is common here, offering you a glimpse into the area's vibrant community spirit.
  • Respecting Residential Privacy: Respect for neighbors and their privacy is highly valued, especially during community gatherings or quiet evenings at your vacation rental.
  • Engaging with Regional Cuisine: Sampling locally favored dishes and supporting small businesses helps you immerse yourself in this area's culinary traditions.
  • Participating in Outdoor Traditions: Enjoying outdoor activities such as local park visits aligns with the area's appreciation for nature and recreational customs.

Frequently Asked Questions About Windermere?

1. What are the top vacation rentals in Windermere?

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

2. How many vacation rentals have private pools in Windermere?

There are 10 vacation rentals with private pools near Windermere. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Windermere are best for families?

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

4. How many Rentbyowner vacation rentals are available in Windermere?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 110 in the Windermere 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 Windermere. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the host and specific property listing. You should review the cancellation terms outlined in the booking details or contact the property owner directly to understand any fees or restrictions.

6. 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 may apply. These will be detailed during the booking process or in the listing description, so it's recommended to read through all the terms before confirming your reservation.

7. How do I confirm the availability and secure my stay at a vacation rental in the region?

Availability can be checked through the listing calendar. Once you find a suitable property, you can proceed with the booking by following the platform’s instructions, which typically involve submitting your details and payment information.

8. What amenities are commonly included in vacation rentals around here?

Most properties offer a range of amenities such as Wi-Fi, parking, fully equipped kitchens, and outdoor spaces. Specific features will be listed in each property’s description, so reviewing these details helps ensure the rental meets your needs.

9. Who do I contact if I have questions about my reservation or the property during my stay?

The property owner or the management team listed in the booking will be your primary point of contact. Contact information is usually provided in your reservation confirmation or within the listing, allowing you to reach out for support or inquiries.