Windermere vacation rentals

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Best Windermere vacation rentals

Most recommended vacation rentals in Windermere

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Peaceful Private Pet Friendly and near everything - Windermere - Outdoors view
Peaceful Private Pet Friendly and near everything
Windermere, FL
Free Wi-Fi
Pet friendly
$230+
Check availability
Luxury 2bd/2 bath Condo Home 254 - Windermere - Pool
Luxury 2bd/2 bath Condo Home 254
Windermere, FL
Pool
Spa
$213+
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4 Bedrooms- 4,5 Bathrooms- Magic Village 7466 Bd - Windermere - Living room
4 Bedrooms- 4,5 Bathrooms- Magic Village 7466 Bd
Windermere, FL
9.5Wonderful(1)
Parking
Free Wi-Fi
Pool
$390+
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Near Disney, amazing, private and comfortable room - Windermere - Building
Near Disney, amazing, private and comfortable room
Windermere, FL
$96+
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Comfy 5br4 Ba With Bbq, Private Pool & Hot Tub - Windermere - Pool
Comfy 5br4 Ba With Bbq, Private Pool & Hot Tub
Windermere, FL
Parking
Free Wi-Fi
Pool
Spa
$251+
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Welcome to the Farm House! Excellent Location, Pet Friendly! - Windermere - Living room
Welcome to the Farm House! Excellent Location, Pet Friendly!
Windermere, FL
$323+
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7664 - Beautiful 3 Bedroom Townhouse by Disney - Windermere - Living room
7664 - Beautiful 3 Bedroom Townhouse by Disney
Windermere, FL
Spa
$215+
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4013 201 Vista Cay - Windermere - Lobby
4013 201 Vista Cay
Windermere, FL
$241+
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Vc13-303 - Modern Decor - Near Major Attractions - Windermere - Lobby
Vc13-303 - Modern Decor - Near Major Attractions
Windermere, FL
Spa
$193+
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Ie2166 Solara Resort 5 Beds 4.5 Baths Private Pool & Free Waterpark - Windermere - Pool
Ie2166 Solara Resort 5 Beds 4.5 Baths Private Pool & Free Waterpark
Windermere, FL
Free Wi-Fi
$271+
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Rustic Hideaway - Modern Estate - Great Location + Pet Friendly! - Windermere - Living room
Rustic Hideaway - Modern Estate - Great Location + Pet Friendly!
Windermere, FL
$375+
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15 min to Disney/ Lakeview Home with Private Pool. - Windermere
15 min to Disney/ Lakeview Home with Private Pool.
Windermere, FL
Free Wi-Fi
Pool
$281+
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Beautiful Vacation Home in Fabulous Resort With Lazy River and Tiki Bar - Windermere
Beautiful Vacation Home in Fabulous Resort With Lazy River and Tiki Bar
Windermere, FL
Pool
$204+
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Beautiful villa close to Disney situated in Orlando's finest suburb - Windermere
Beautiful villa close to Disney situated in Orlando's finest suburb
Windermere, FL
Pool
$514+
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Wonderful Home Private Pool 8900 N - Windermere
Wonderful Home Private Pool 8900 N
Windermere, FL
10Wonderful(2)
Spa
$300+
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Beautiful 4 bedroom Condo near Disney with pool. - Windermere
Beautiful 4 bedroom Condo near Disney with pool.
Windermere, FL
Free Wi-Fi
Pool
$387+
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Good to know

Low season

March

High season

November

Average price (weeknight)

$254

Average price (weekend night)

$323
Cheapest month to stay with an average 59% drop in price.
Most expensive month to stay with an average 40% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Windermere vacation rental deals

  • The best vacation rental properties in Windermere are New 3br Aladdin & Princess Jasmine Moroccan Luxe Suite Baby Friendly Near Disney (9.8, 36 reviews), FA4381 Storey Lake Home 4Beds 3baths Private Pool and Free Waterpark (9.1, 20) and FA4381 Storey Lake Home 4Beds 3baths Private Pool and Free Waterpark (9.1, 20), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Windermere, you should consider visiting during the low season. The cheapest vacation homes in Windermere can be found in March and June.
  • The cheapest night for renting a vacation home in Windermere is Tuesday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Windermere for 11 days.

FAQs when booking a vacation home in Windermere

  • What types of vacation rentals are available in Windermere?

    There are loads of different property types that you can make your vacation home in Windermere. You’ll find apartments, condos, houses and villas.

  • Are there any pet-friendly vacation rentals in Windermere?

    There are a number of dog and pet-friendly Windermere vacation rentals, with around 2% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Windermere?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Windermere?

Our map will help you find the perfect place to stay in Windermere by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Windermere

Windermere vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Windermere. Find cheap vacation homes to rent in Windermere. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Windermere that suits you best.

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