Vacation rentals in Windermere
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Top-rated vacation rentals in Windermere
Guests agree: these stays are highly rated for location, cleanliness, and more.
Guesthouse in Orlando
4.94 out of 5 average rating, 207 reviewsModern Guest Studio (Private) Pool / Spa available
Private Guest Studio (Not Shared ) in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. Pool & Spa available (Not Shared) All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.
Dec. 31 – Jan. 7
Home in Winter Garden
4.92 out of 5 average rating, 164 reviewsCozy Winter Garden Home 20 MINUTES FROM DISNEY
Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.
May 1 – 8
Cottage in Winter Garden
4.99 out of 5 average rating, 102 reviewsCome Stay In The Heart Of Winter Garden
Stay in a completely renovated 1937 cottage that's located in the heart of historic downtown Winter Garden. It's walking distance from all of the shops, restaurants, and events (including the #1 rated farmers market in the nation every Saturday) that make Winter Garden one of the most desirable cities in Florida. Sit on the front porch and watch as people bike and jog on the famous West Orange Trail, or rent a bike from the corner and join them. The home is close to all major highways.
Aug. 20 – 27
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Windermere vacation rentals
Other great vacation rentals in Windermere
Home in Orlando
4.94 out of 5 average rating, 227 reviewsNew studio in a newly renovated House
Oct. 21 – 28
Guesthouse in Orlando
4.82 out of 5 average rating, 435 reviewsSpacious getaway close to Universal and Outlets!
Nov. 22 – 29
Home in Apopka
4.96 out of 5 average rating, 184 reviewsFarm feel in the city
Jan. 30 – Feb. 6
Apartment in Windermere
5.0 out of 5 average rating, 17 reviews1BR Cozy Oasis+King Bed+Fast WiFi+Pool+Gym
Aug. 16 – 23
Apartment in Windermere
4.83 out of 5 average rating, 52 reviewsPrivate Garage Apt., 5 Miles from Disney World
Oct. 7 – 14
Apartment in Windermere
5.0 out of 5 average rating, 17 reviews2BD Apt+LakeView+Balcony, Resort Style Pool, Wi-Fi
May 25 – Jun. 1
Condo in Windermere
5.0 out of 5 average rating, 11 reviewsLuXury Apt with Lake View, Cable & fast WiFi
Aug. 31 – Sep. 7
Home in Winter Garden
4.88 out of 5 average rating, 16 reviewsPet Friendly Winter Garden Get-Away near Orlando
Sep. 22 – 29
Guesthouse in Winter Garden
4.94 out of 5 average rating, 47 reviewsBlue Heron Bungalow
Jul. 11 – 18
Home in Winter Garden
4.94 out of 5 average rating, 17 reviewsCozy home in Winter Garden
Jul. 4 – 11
Apartment in Ocoee
4.96 out of 5 average rating, 47 reviewsCompletely Private and Cozy Studio
Aug. 8 – 15
Cottage in Winter Garden
4.89 out of 5 average rating, 84 reviews3 br/2 ba Downtown Winter Garden Cottage w\fence
Mar. 22 – 27
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