Windermere houses
We found 26,002 houses — enter your dates for availability
Explore Windermere house rentals
Orlando 20 Guest Villa Centrally Located with Game Room
Sleeps 20 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
The Home of Sweet Peace
Sleeps 6 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
61 reviews(61 reviews)
Rustic Hideaway - Modern Estate - Great Location + Pet Friendly!
Sleeps 11 · 5 bedrooms · 4 bathrooms
6.46.4 out of 10
5 reviews(5 reviews)
Last Minute Disney Getaway! Luxury Villa with Private Pool. Book Now! #115911
Sleeps 11 · 5 bedrooms · 4 bathrooms
Beautiful Private gated Lakefront estate in Windermere on 2 acres of land!!!
Sleeps 6 · 3 bedrooms · 2 bathrooms
2.02.0 out of 10
1 review(1 review)
Welcome to the Farm House! Excellent Location, Pet Friendly!
Sleeps 12 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
Top rated house rentals - Windermere
Excellent Accommodation
1010 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
Wonderful house
1010 out of 10
Exceptionalexceptional
111 reviews(111 reviews)
Fabulous
1010 out of 10
Exceptionalexceptional
171 reviews(171 reviews)
Lovely Villa
1010 out of 10
Exceptionalexceptional
73 reviews(73 reviews)
Exceptional property for multi generational holiday
1010 out of 10
Exceptionalexceptional
218 reviews(218 reviews)
Fantastic stay
1010 out of 10
Exceptionalexceptional
183 reviews(183 reviews)
Orlandos finest villa
1010 out of 10
Exceptionalexceptional
93 reviews(93 reviews)
great for family
1010 out of 10
Exceptionalexceptional
105 reviews(105 reviews)
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Frequently asked questions
Are there any holiday home rentals in Windermere?
Check out our 26,002 holiday home rentals and start planning your Windermere trip. Whether you're staying in Bay Hill, Metro West, Windhover or another well-known area, you'll find the ideal house on Vrbo.
How much does it cost to stay in a holiday rental house in Windermere?
Explore a variety of holiday home rentals in Windermere, where there's a price to suit every preference. From budget-friendly picks to upmarket properties, Vrbo makes it a cinch to compare options and narrow your search to find the ultimate stay for your getaway.
When is the best time to rent a holiday house in Windermere?
The best time is whenever you can break free from your daily routine and enjoy the weather you love. For many people searching for a holiday home rental in Windermere, Orlando, that's February. Average daily temperatures during this month range from 14ºC (57ºF) to 23ºC (73ºF).
Where can I rent a Windermere holiday house with great views?
There's only one thing better than spending your break in one of our Windermere holiday home rentals — staying somewhere that comes with epic views. Scroll through our options to discover a house with the amenities you need and the outlooks that'll make your getaway even more memorable. Sort your results by "Guest rating" or "Recommended" and see what comes up.
Does Windermere have any weekend house rentals?
Explore our weekend rentals and prepare for an action-packed few days away. Our main tips for booking the ideal house in Windermere? Be flexible when searching and modify your dates until you find the holiday home rental that fits your style.
Are there any pet-friendly house rentals in Windermere?
Use our convenient filter tool to browse pet-friendly holiday home rentals in Windermere. To discover a house rental that provides perks such as an enclosed outdoor space or pet bedding, simply click on "Pets allowed."
What are the top things to do in Windermere?
Get your Windermere getaway off to an awesome start by visiting popular sights like Universal Studios Florida, Magic Kingdom® Park and Disney's Animal Kingdom® Theme Park. Stay in a Vrbo holiday home rental with the family and then discover this destination's wonders together.
Why should I book my holiday rental house with Vrbo?
From houses in quiet rural villages to those in bustling city centres, Vrbo has a wide variety of holiday home rentals to choose from. One of the best things about us? You'll never have to share your place with any other guests. Plus, with our One Key™ rewards programme, you can collect OneKeyCash™* and redeem it on all eligible bookings across Vrbo. And with flexible cancellation policies and support throughout your trip, we'll make sure everything goes smoothly. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.