Windermere vacation rentals
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Top-rated vacation rentals in Windermere
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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
Tiny home in Orlando
4.98 out of 5 average rating, 625 reviewsThe 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.
Aug 11 – 18
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
Home in Apopka
4.96 out of 5 average rating, 184 reviewsFarm feel in the city
Aug 20 – 27
Guesthouse in Orlando
4.82 out of 5 average rating, 435 reviewsSpacious getaway close to Universal and Outlets!
Nov 22 – 29
Guesthouse in Orlando
4.8 out of 5 average rating, 195 reviewsLuxury 5 star home 3 min Universal/ Orlando City
Jun 9 – 16
Vacation home in Orlando
4.82 out of 5 average rating, 100 reviewsThe Lovers Haven (Romantic Studio w/ Balcony)
Jul 17 – 24
Townhouse in Winter Park
4.98 out of 5 average rating, 195 reviewsBeautiful Downtown Winter Park
Jun 15 – 22
Guesthouse in Orlando
4.99 out of 5 average rating, 194 reviewsLivingston Pool House- In The Heart of Downtown
Nov 12 – 19
Guest suite in Orlando
4.94 out of 5 average rating, 188 reviewsLuxury Suite Near Disney & Downtown Orlando
Apr 6 – 13
Guest suite in Clermont
4.83 out of 5 average rating, 125 reviewsClermont Guest Suite
May 10 – 17
Apartment in Orlando
4.95 out of 5 average rating, 153 reviewsPrívate studio apartment
Jun 4 – 11
Guesthouse in Clermont
4.95 out of 5 average rating, 129 reviewsModern efficiency ~ Great location
Jun 3 – 10
Apartment in Winter Park
4.95 out of 5 average rating, 280 reviewsGet a Little Glam in a Retro Palm Beach-Style Boudoir
Nov 1 – 8
Other great vacation rentals in Windermere
Condo in Kissimmee
4.89 out of 5 average rating, 132 reviews2BD/2BA condo close to Disney at Storey Lake #96
Sep 25 – Oct 2
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, 18 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
Nov 10 – 17
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
Farm stay in Winter Garden
4.95 out of 5 average rating, 44 reviewsCarriage House Studio Apt Peaceful & Private Ranch
Nov 20 – 27
Apartment in Windermere
4.94 out of 5 average rating, 16 reviews1BDR+Peaceful Stay+FastWifi+ Free Parking+Pool+Gym
Jul 1 – 8
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