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.

Guest favourite

Guesthouse in Orlando

4.94 out of 5 average rating, 207 reviews

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.

Dec. 31 – Jan. 7

$191 CAD per night
Guest favourite

Home in Winter Garden

4.92 out of 5 average rating, 164 reviews

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.

May 1 – 8

$188 CAD per night
Guest favourite

Cottage in Winter Garden

4.99 out of 5 average rating, 102 reviews

Come 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

$297 CAD per night

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

4.94 out of 5 average rating, 227 reviews

New studio in a newly renovated House

Oct. 21 – 28

$158 CAD per night
Guest favourite

Guesthouse in Orlando

4.82 out of 5 average rating, 435 reviews

Spacious getaway close to Universal and Outlets!

Nov. 22 – 29

$169 CAD per night
Guest favourite

Home in Apopka

4.96 out of 5 average rating, 184 reviews

Farm feel in the city

Jan. 30 – Feb. 6

$213 CAD per night
Guest favourite

Apartment in Windermere

5.0 out of 5 average rating, 17 reviews

1BR Cozy Oasis+King Bed+Fast WiFi+Pool+Gym

Aug. 16 – 23

$231 CAD per night
Superhost

Apartment in Windermere

4.83 out of 5 average rating, 52 reviews

Private Garage Apt., 5 Miles from Disney World

Oct. 7 – 14

$195 CAD per night
Guest favourite

Apartment in Windermere

5.0 out of 5 average rating, 17 reviews

2BD Apt+LakeView+Balcony, Resort Style Pool, Wi-Fi

May 25 – Jun. 1

$279 CAD per night
Guest favourite

Condo in Windermere

5.0 out of 5 average rating, 11 reviews

LuXury Apt with Lake View, Cable & fast WiFi

Aug. 31 – Sep. 7

$237 CAD per night
Guest favourite

Home in Winter Garden

4.88 out of 5 average rating, 16 reviews

Pet Friendly Winter Garden Get-Away near Orlando

Sep. 22 – 29

$133 CAD per night
Guest favourite

Guesthouse in Winter Garden

4.94 out of 5 average rating, 47 reviews

Blue Heron Bungalow

Jul. 11 – 18

$166 CAD per night
Guest favourite

Home in Winter Garden

4.94 out of 5 average rating, 17 reviews

Cozy home in Winter Garden

Jul. 4 – 11

$212 CAD per night
Guest favourite

Apartment in Ocoee

4.96 out of 5 average rating, 47 reviews

Completely Private and Cozy Studio

Aug. 8 – 15

$125 CAD per night
Guest favourite

Cottage in Winter Garden

4.89 out of 5 average rating, 84 reviews

3 br/2 ba Downtown Winter Garden Cottage w\fence

Mar. 22 – 27

$292 CAD per night

Destinations to explore

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  3. Florida
  4. Orange County
  5. Windermere