Find Vacation Rentals in Windermere

We have 57 properties to choose from
Windermere
Anytime
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Windermere
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Popular Windermere Vacation Rentals

Find the perfect Windermere vacation rental

House Windermere
$353 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (2 ratings)
Windermere, Orange County, Florida, United States
Details
Vrbo
Details
Details
House Windermere
$396 per night
House ∙ 9 guests ∙ 4 bedrooms
Windermere, Orange County, Florida, United States
Details
Vrbo
Details
Details
Villa Windermere
$229 per night
Villa ∙ 11 guests ∙ 3 bedrooms
4.5
Excellent (4 ratings)
Windermere, Orange County, Florida, United States
Details
Vrbo
Details
Details
House Windermere
$456 per night
House ∙ 12 guests ∙ 4 bedrooms
4.5
Excellent (184 ratings)
Windermere, Orange County, Florida, United States
Details
Vrbo
Details
Details
House Windermere
$270 per night
House ∙ 8 guests ∙ 5 bedrooms
4.9
Outstanding (6 ratings)
Windermere, Orange County, Florida, United States
Details
Vrbo
Details
Details
Apartment Windermere
$177 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Windermere, Orange County, Florida, United States
Details
Vrbo
Details
Details
Apartment Windermere
$168 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Windermere, Orange County, Florida, United States
Details
Vrbo
Details
Details
House Windermere
$126 per night
House ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (4 ratings)
Windermere, Orange County, Florida, United States
Details
Vrbo
Details
Details
House Windermere
$492 per night
House ∙ 6 guests ∙ 4 bedrooms
5.0
Outstanding (71 ratings)
Windermere, Orange County, Florida, United States
Details
Vrbo
Details
Details
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Vacation rentals and apartments with air conditioning

House  Windermere
$414 per night
House ∙ 8 guests ∙ 4 bedrooms
Windermere, Orange County, Florida, United States
Air conditioning
Details
Vrbo
Details
Details
House  Windermere
$179 per night
House ∙ 4 guests ∙ 1 bedroom
Windermere, Orange County, Florida, United States
Air conditioning
Details
Vrbo
Details
Details
Apartment  Windermere
$453 per night
Apartment ∙ 8 guests ∙ 1 bedroom
3.0
(1 rating)
Windermere, Orange County, Florida, United States
Air conditioning
Details
Expedia
Details
Details
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Vacation rentals with Wi-Fi

Apartment  Windermere
$209 per night
Apartment ∙ 8 guests ∙ 1 bedroom
4.9
Outstanding (7 ratings)
Windermere, Orange County, Florida, United States
Internet
Details
Expedia
Details
Details
Apartment  Windermere
$281 per night
Apartment ∙ 5 guests ∙ 1 bedroom
5.0
Outstanding (2 ratings)
Windermere, Orange County, Florida, United States
Internet
Details
HomeToGo
Details
Details
House  Windermere
$426 per night
House ∙ 12 guests ∙ 4 bedrooms
Windermere, Orange County, Florida, United States
Internet
Details
Vrbo
Details
Details
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Apartments and vacation rentals with a kitchen

Apartment  Windermere
$464 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Windermere, Orange County, Florida, United States
Kitchen
Details
HomeToGo
Details
Details
Villa  Windermere
$268 per night
Villa ∙ 11 guests ∙ 5 bedrooms
Windermere, Orange County, Florida, United States
Kitchen
Details
Vrbo
Details
Details
Apartment  Windermere
$136 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (2 ratings)
Windermere, Orange County, Florida, United States
Kitchen
Details
Vrbo
Details
Details
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Frequently Asked Questions

How much does a night in a vacation rental cost in Windermere on average?

Prices for a stay in Windermere begin at $126 per night.

How many vacation rentals are available in Windermere?

On tripping.com, you will find 57 available vacation rental offers in Windermere.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Windermere

Find the best Windermere vacation rentals on Tripping.com. With over 1589 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Windermere range from $37 a night. Many rentals can also be booked directly online. Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 1396 homes in Windermere offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 96 rentals with pool or jacuzzi, or relax with the family in one of the 1245 homes with cable TV. For all those pet owners with dogs or cats, Windermere offers 315 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com. Search properties from 11 vacation rental sites in Windermere where the top providers in that area are Booking.com, Expedia, and HomeAway. There are 645 Booking.com rentals, 365 Expedia short term rentals and 253 HomeAway vacation rentals.

Popular Day Trips Near Windermere

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