Windermere Cottage Rentals By Owner

Windermere Cottage Rentals

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Price Dropped

Cottage

Shore Steps Cottage - Walking Distance To The Town Of Windermere

1 Bedroom 1 Bath 3 Guests

AU $277/Night 7 Nights - AU $1,937

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Apartment

New 1 Bedroom suite with full kitchen, living room and bathroom

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath 3 Guests

AU $164/Night 7 Nights - AU $1,151

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Villa

Luxury Retreat in Windermere The Perfect Base for Exploring Orlando

10.0

Exceptional

(1 Review)

5 Bedrooms 3 Baths 11 Guests 3100.01 ft²

AU $314/Night 7 Nights - AU $2,197

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The Farm House - Great Location + Pet Friendly!

Villa

The Farm House - Great Location + Pet Friendly!

1 Bedroom 1 Bath

AU $856/Night 7 Nights - AU $5,994

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House

150-Yards To Arnold Palmer’s Bay Hill Clubhouse!

2 Bedrooms 2 Baths 6 Guests

AU $6,063/Night 7 Nights - AU $42,443

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Resort

Arnold Palmer's Bay Hill Club & Lodge

9.4

Exceptional

(74 Reviews)

9 Baths 18 Guests 630.46 ft²

AU $389/Night 7 Nights - AU $2,721

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House

Near Disney, amazing, private and comfortable room

1 Bedroom 1 Bath 28 Guests

AU $129/Night 7 Nights - AU $905

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Apartment

Resort condo near Disney Free parks shuttle

7.2

Very Good

(5 Reviews)

1 Bedroom 1 Bath 6 Guests 548.96 ft²

AU $216/Night 7 Nights - AU $1,510

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Apartment

1 Bedroom Lofted, Private entrance, dedicated parking, W/D, WiFi

1 Bedroom 1 Bath 2 Guests

AU $115/Night 7 Nights - AU $802

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7 Mi to Disney World: Orlando Home w/Private Pool

House

7 Mi to Disney World: Orlando Home w/Private Pool

3 Bedrooms 2 Baths 10 Guests 1625.35 ft²

AU $259/Night 7 Nights - AU $1,811

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Highly Rated

House

The Home of Sweet Peace

10.0

Exceptional

(61 Reviews)

4 Bedrooms 3 Baths 6 Guests 2000 ft²

AU $954/Night 7 Nights - AU $6,680

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House

Beautiful 4 Bedroom Home

10.0

Exceptional

(1 Review)

4 Bedrooms 4 Baths 8 Guests

AU $506/Night 7 Nights - AU $3,545

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More Top-Rated Cottage Rentals in Windermere Area

Why Choose Rent By Owner for your Windermere Cottage Rentals?

What makes our Cottage Rentals special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Windermere

How to Book Your Windermere Cottage Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cottage rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

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 Cottage Rentals in Windermere Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage 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

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Frequently Asked Questions About Windermere Rental Cottages

1. What are the top Cottages 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 Cottages in Windermere:

2. How many Cottages are available in Windermere?

Currently, the total number of properties listed by RBO in 2026 is over 1 in the Windermere area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Windermere. 