Vacation rentals in Windermere

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windermere

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guesthouse in Orlando
Modern 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.
Oct. 8 – 15
$191 CAD per night
4.94 out of 5 average rating, 206 reviews
Guest favourite
Home in Winter Garden
Cozy 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.
Aug. 1 – 8
$187 CAD per night
4.92 out of 5 average rating, 164 reviews
Guest favourite
Tiny homes in Orlando
The Little Treehouse 2 at Country Club of Orlando
With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.
Oct. 17 – 24
$201 CAD per night
4.98 out of 5 average rating, 624 reviews

Popular amenities for Windermere vacation rentals

Stay near Windermere's top sights

Dixie Cream Cafe10 locals recommend
United States Postal Service3 locals recommend
Paloma Coffee Co.3 locals recommend

Other great vacation rentals in Windermere

Guest favourite
Home in Orlando
New studio in a newly renovated House
Sep. 9 – 16
$156 CAD per night
4.94 out of 5 average rating, 224 reviews
Guest favourite
Apartment in Windermere
1BR Cozy Oasis+King Bed+Fast WiFi+Pool+Gym
Apr. 26 – May 3
$230 CAD per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Apartment in Windermere
1BDR+Peaceful Stay+FastWifi+ Free Parking+Pool+Gym
Jul. 7 – 14
$239 CAD per night
4.94 out of 5 average rating, 16 reviews
Superhost
Apartment in Windermere
Private Garage Apt., 5 Miles from Disney World
Sep. 28 – Oct. 5
$194 CAD per night
4.82 out of 5 average rating, 50 reviews
Guest favourite
Apartment in Windermere
2BD Apt+LakeView+Balcony, Resort Style Pool, Wi-Fi
Jun. 6 – 13
$271 CAD per night
5.0 out of 5 average rating, 15 reviews
Guest favourite
Condo in Windermere
LuXury Apt with Lake View, Cable & fast WiFi
Aug. 30 – Sep. 6
$260 CAD per night
5.0 out of 5 average rating, 11 reviews
Guest favourite
Guesthouse in Orlando
Cozy 1BR/1BA Guesthouse Close to Universal/Parks
Apr. 10 – 17
$151 CAD per night
4.9 out of 5 average rating, 31 reviews
Guest favourite
Home in Winter Garden
Winter Garden Experience
Jun. 15 – 22
$225 CAD per night
4.9 out of 5 average rating, 41 reviews
Guest favourite
Guesthouse in Winter Garden
Blue Heron Bungalow
Nov. 9 – 16
$165 CAD per night
4.93 out of 5 average rating, 46 reviews
Guest favourite
Cottage in Winter Garden
Come Stay In The Heart Of Winter Garden
Aug. 29 – Sep. 5
$296 CAD per night
4.99 out of 5 average rating, 101 reviews
Guest favourite
Home in Winter Garden
Cozy home in Winter Garden
Jul. 15 – 22
$211 CAD per night
4.94 out of 5 average rating, 17 reviews
Superhost
Home in Windermere
Water Front Haven
May 26 – Jun. 2
$514 CAD per night
4.91 out of 5 average rating, 22 reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Windermere