Discover Your Perfect Windermere Villa

Windermere Villa

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Why Choose Rent By Owner for your Windermere Villa?

What makes our Villa 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 Windermere Villa

Where are the best neighborhoods to stay in Windermere?

Choosing to stay in the Windermere neighborhood offers a serene and family-friendly atmosphere, perfect for relaxing getaways. The area is known for its charming residential streets and close proximity to local attractions, making it an ideal base for exploring the region. Whether you prefer a peaceful retreat or convenient access to nearby amenities, Windermere provides a dependable and comfortable setting for your villa stay.

Bay Lake

This area offers convenient access to the famous attractions while providing a peaceful retreat, making it an ideal choice for those seeking relaxation near the vibrant entertainment hub of the region.

View 997+ Rentals in Bay Lake

Southwest Orlando

Widely regarded as a prime location for exploring all that this destination has to offer, the neighborhood features easy routes to popular attractions and a variety of comfortable villas for your stay.

View 965+ Rentals in Southwest Orlando

Metro West

Known for its convenient proximity to central Orlando, this part of the area provides excellent options for travelers looking to enjoy both leisure and local conveniences during their vacation.

View 433+ Rentals in Metro West

Best Times to Visit Windermere

When should you plan your Villa stay?

To make the most of your stay and enjoy the area's pleasant weather, it's ideal to plan your vacation during the cooler months, when visiting here offers a comfortable and enjoyable experience in the region known for its welcoming atmosphere and reliable accommodations.

Peak Season Highlights

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Spring (March to May)

During the spring months, you can enjoy pleasant weather with mild temperatures, making it ideal for exploring the area around Windermere. This is when the region experiences a surge in visitors seeking outdoor activities and relaxing villa stays.

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

The winter holiday season attracts travelers looking for festive escapes, offering cooler temperatures and an inviting atmosphere. This period often features increased demand for private villas designed for cozy and comfortable retreats in this destination.

Average Temperature Daytime: 68°F - Nighttime: 48°F

Off-Season Highlights

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Summer (June to August)

While summer generally draws many visitors, early and late summer tend to be quieter, providing a more relaxed experience for those booking villas here. The warm weather creates perfect conditions for enjoying outdoor leisure at your own pace.

Average Temperature Daytime: 88°F - Nighttime: 70°F
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Fall (September to November)

In the fall, the region becomes less crowded as temperatures cool slightly, offering a peaceful setting for your villa stay. It's an excellent time to enjoy the area's natural beauty without the peak season crowds.

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

Weekly Weather Forecast for Windermere

How to Book Your Windermere Villa

What's our booking process?

Our platform allows you to browse a curated selection of villa. 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 Villa in Windermere Area

Common Villa Amenities

What amenities can you expect?

Our Villa 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 unwind after exploring the area.
  • Take advantage of spacious patios or decks perfect for outdoor dining and entertaining.
  • Benefit from lush gardens or landscaped yards that enhance your outdoor experience.
  • Make use of outdoor grilling stations for delicious barbecues with family and friends.
  • Find comfort in shaded lounging areas designed for sunny Florida afternoons.
  • Utilize well-maintained tennis courts or sports facilities available on some properties.
  • Access nearby parks or walking trails to embrace the natural beauty of this destination.

Top Attractions Around Windermere

What attractions are nearby?

In this destination, you can enjoy a variety of outdoor activities and scenic pursuits just moments from your accommodation, including lakeside boating, nature trails, and family-friendly parks that showcase the natural beauty and recreational options of the region.

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Family Activities

  • Lake Windsong Park: Enjoy a family picnic and outdoor activities surrounded by scenic views in this popular park in the area.
  • The Windermere Recreation Center: Participate in sports, recreational programs, or just relax in the welcoming community space suitable for all ages.
  • Local Water Activities: Experience boat rentals or kayaking on the nearby lakes, offering fun-filled water adventures for the whole family.
  • Family-Friendly Dining Options: Discover a variety of casual restaurants and cafes in the region that cater to guests seeking convenient and delicious meal options.
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Adult Activities

  • Lake Windermere Tours: Enjoy a relaxing boat tour on the pristine waters of Lake Windermere, offering stunning views and a peaceful escape within the area.
  • Golfing at Windermere Golf Club: Play a round of golf on one of the region’s well-maintained courses, ideal for making the most of your visit to this picturesque destination.
  • Visit local vineyards and wineries: Explore nearby vineyards where you can indulge in wine tastings and learn about the regional wine-making traditions.
  • Fine Dining Experiences: Savor delectable cuisine at the area’s top restaurants, providing a perfect setting for memorable evenings during your stay.

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Windermere Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Book your preferred villas early to secure the best options and enjoy a smooth stay in this popular destination.
  • Explore Local Dining: Take advantage of nearby restaurants and cafes to sample regional flavors and enhance your experience here.
  • Utilize Outdoor Activities: Make the most of the area's outdoor offerings by scheduling activities that allow you to relax and unwind in this scenic region.
  • Access Local Tips: Consult trusted sources or local guides to discover hidden gems and make the most of your time in this vibrant destination.

Transportation Options

  • Rental Car Services: Renting a vehicle is a convenient way to explore Windermere and the surrounding region at your own pace.
  • Shuttle Services: Reliable shuttle options operate regularly between key points in the area, making them an efficient choice for transportation.
  • Taxi and Ride-Sharing: Taxis and popular ride-sharing apps provide quick and flexible transportation around Windermere, ideal for short trips or last-minute plans.
  • Public Transportation: Local bus services connect you to nearby attractions and towns, offering an economical way to navigate this destination without hassle.

Local Customs Options

  • Holidays and Festivals: Celebrating local holidays with community events and parades is a cherished tradition here, offering an authentic taste of the area's vibrant culture.
  • Southern Hospitality: Guests often experience warm welcomes and friendly gestures, reflecting the region's reputation for genuine hospitality and courteous manners.
  • Dining Etiquette: Sharing meals at local gatherings emphasizes the importance of communal eating and respectful conversation in this welcoming community.
  • Respect for Nature: Maintaining cleanliness and respecting outdoor spaces is highly valued, ensuring visitors contribute positively to the area's natural beauty.

Frequently Asked Questions About Windermere Rental Villas

1. What are the top Villas 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 Villas in Windermere:

2. How many Villas are available in Windermere?

Currently, the total number of properties listed by RBO in 2026 is over 7 in the Windermere area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Villas in Windermere. 

3. What is the cancellation policy for villas in this area?

Cancellation policies vary depending on the specific villa you choose. It is recommended to review the individual listing details or contact the property owner directly to understand the terms related to cancellations, refunds, and any applicable fees.

4. Are there any additional fees I should be aware of when booking a villa here?

Additional fees such as cleaning charges, security deposits, or service fees may apply. These details are typically outlined in the property listing, so it's best to read the description carefully or reach out to the owner for clarification.

5. What amenities are usually included with villas in this destination?

Most villas offer amenities like private pools, full kitchens, Wi-Fi, and outdoor spaces. However, amenities can vary, so review each listing thoroughly or contact the owner to confirm what’s included during your stay.

6. How do I ensure my reservation is secure when booking a villa here?

Reservations made through a trusted platform are protected by secure payment systems. Always verify the listing details and communicate through the platform to ensure your booking is confirmed and protected against potential issues.

7. Is there a minimum stay requirement for villas in this region?

Many properties have minimum stay requirements, especially during peak seasons. Check the specific listing details or contact the owner directly to confirm the minimum nights needed for your desired travel dates.

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