Find Vacation Rentals in Windermere

We have 57 properties to choose from
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Popular Windermere Vacation Rentals

Find the perfect Windermere vacation rental

Villa Windermere
from $231 per night
Villa ∙ 11 guests ∙ 3 bedrooms

263 m² Villa

4.5
Excellent(4 ratings)
Windermere, Orange County, Florida, United States
Vrbo
Details
House Windermere
from $127 per night
5 guests ∙ 3 bedrooms

House

5.0
Outstanding(6 ratings)
Windermere, Orange County, Florida, United States
Vrbo
Details
Condo Windermere
from $130 per night
Condo ∙ 4 guests ∙ 1 bedroom

92 m² Condo

5.0
Outstanding(1 rating)
Windermere, Orange County, Florida, United States
Vrbo
Details
Apartment Windermere
from $326 per night
6 guests ∙ 2 bedrooms

Apartment

Windermere, Orange County, Florida, United States
Vrbo
Details
House Windermere
from $391 per night
6 guests ∙ 3 bedrooms

House

Windermere, Orange County, Florida, United States
Vrbo
Details
House Windermere
from $235 per night
House ∙ 10 guests ∙ 3 bedrooms

150 m² House

Windermere, Orange County, Florida, United States
HomeToGo
Details
House Windermere
from $522 per night
House ∙ 6 guests ∙ 4 bedrooms

186 m² House

5.0
Outstanding(71 ratings)
Windermere, Orange County, Florida, United States
Vrbo
Details
Apartment Windermere
from $106 per night
2 guests ∙ 1 bedroom

Apartment

Windermere, Orange County, Florida, United States
Vrbo
Details
House Windermere
from $414 per night
9 guests ∙ 4 bedrooms

House

Windermere, Orange County, Florida, United States
Vrbo
Details
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Vacation rentals and apartments with air conditioning

House  Windermere
from $223 per night
6 guests ∙ 3 bedrooms

House

Windermere, Orange County, Florida, United States
Air conditioning
Vrbo
Details
House  Windermere
from $376 per night
11 guests ∙ 4 bedrooms

House

3.9
Good(8 ratings)
Windermere, Orange County, Florida, United States
Air conditioning
Vrbo
Details
House  Windermere
from $211 per night
20 guests ∙ 4 bedrooms

House

5.0
Outstanding(6 ratings)
Windermere, Orange County, Florida, United States
Air conditioning
Vrbo
Details
Show more

Vacation rentals with Wi-Fi

House  Windermere
from $349 per night
11 guests ∙ 4 bedrooms

House

4.5
Excellent(4 ratings)
Windermere, Orange County, Florida, United States
Internet
Vrbo
Details
House  Windermere
from $497 per night
11 guests ∙ 5 bedrooms

House

Windermere, Orange County, Florida, United States
Internet
Vrbo
Details
Apartment  Windermere
from $297 per night
5 guests ∙ 1 bedroom

Apartment

4.8
Outstanding(6 ratings)
Windermere, Orange County, Florida, United States
Internet
HomeToGo
Details
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Apartments and vacation rentals with a kitchen

House  Windermere
from $720 per night
12 guests ∙ 4 bedrooms

House

Windermere, Orange County, Florida, United States
Kitchen
Vrbo
Details
House  Windermere
from $321 per night
House ∙ 12 guests ∙ 3 bedrooms

263 m² House

Windermere, Orange County, Florida, United States
Kitchen
Vio.com
Details
House  Windermere
from $172 per night
5 guests ∙ 3 bedrooms

House

Windermere, Orange County, Florida, United States
Kitchen
Vio.com
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 $91 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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