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.

Guest favorite

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

$95 per night
Guest favorite

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

$151 per night
Guest favorite

Tiny home in Orlando

4.98 out of 5 average rating, 625 reviews

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.

Aug 11 – 18

$111 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 favorite

Home in Orlando

4.94 out of 5 average rating, 227 reviews

New studio in a newly renovated House

Oct 21 – 28

$84 per night
Guest favorite

Home in Apopka

4.96 out of 5 average rating, 184 reviews

Farm feel in the city

Aug 20 – 27

$109 per night
Guest favorite

Guesthouse in Orlando

4.82 out of 5 average rating, 435 reviews

Spacious getaway close to Universal and Outlets!

Nov 22 – 29

$88 per night
Superhost

Guesthouse in Orlando

4.8 out of 5 average rating, 195 reviews

Luxury 5 star home 3 min Universal/ Orlando City

Jun 9 – 16

$93 per night
Guest favorite

Vacation home in Orlando

4.82 out of 5 average rating, 100 reviews

The Lovers Haven (Romantic Studio w/ Balcony)

Jul 17 – 24

$112 per night
Guest favorite

Townhouse in Winter Park

4.98 out of 5 average rating, 195 reviews

Beautiful Downtown Winter Park

Jun 15 – 22

$109 per night
Guest favorite

Guesthouse in Orlando

4.99 out of 5 average rating, 194 reviews

Livingston Pool House- In The Heart of Downtown

Nov 12 – 19

$180 per night
Guest favorite

Guest suite in Orlando

4.94 out of 5 average rating, 188 reviews

Luxury Suite Near Disney & Downtown Orlando

Apr 6 – 13

$89 per night
Guest favorite

Guest suite in Clermont

4.83 out of 5 average rating, 125 reviews

Clermont Guest Suite

May 10 – 17

$66 per night
Guest favorite

Apartment in Orlando

4.95 out of 5 average rating, 153 reviews

Prívate studio apartment

Jun 4 – 11

$100 per night
Guest favorite

Guesthouse in Clermont

4.95 out of 5 average rating, 129 reviews

Modern efficiency ~ Great location

Jun 3 – 10

$68 per night
Guest favorite

Apartment in Winter Park

4.95 out of 5 average rating, 280 reviews

Get a Little Glam in a Retro Palm Beach-Style Boudoir

Nov 1 – 8

$99 per night

Other great vacation rentals in Windermere

Guest favorite

Condo in Kissimmee

4.89 out of 5 average rating, 132 reviews

2BD/2BA condo close to Disney at Storey Lake #96

Sep 25 – Oct 2

$102 per night
Guest favorite

Apartment in Windermere

5.0 out of 5 average rating, 17 reviews

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

Aug 16 – 23

$117 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

$99 per night
Guest favorite

Apartment in Windermere

5.0 out of 5 average rating, 18 reviews

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

May 25 – Jun 1

$144 per night
Guest favorite

Condo in Windermere

5.0 out of 5 average rating, 11 reviews

LuXury Apt with Lake View, Cable & fast WiFi

Aug 31 – Sep 7

$135 per night
Guest favorite

Home in Winter Garden

4.88 out of 5 average rating, 16 reviews

Pet Friendly Winter Garden Get-Away near Orlando

Sep 22 – 29

$69 per night
Guest favorite

Guesthouse in Winter Garden

4.94 out of 5 average rating, 47 reviews

Blue Heron Bungalow

Nov 10 – 17

$89 per night
Guest favorite

Home in Winter Garden

4.94 out of 5 average rating, 17 reviews

Cozy home in Winter Garden

Jul 4 – 11

$116 per night
Guest favorite

Apartment in Ocoee

4.96 out of 5 average rating, 47 reviews

Completely Private and Cozy Studio

Aug 8 – 15

$69 per night
Guest favorite

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

$150 per night
Guest favorite

Farm stay in Winter Garden

4.95 out of 5 average rating, 44 reviews

Carriage House Studio Apt Peaceful & Private Ranch

Nov 20 – 27

$129 per night
Superhost

Apartment in Windermere

4.94 out of 5 average rating, 16 reviews

1BDR+Peaceful Stay+FastWifi+ Free Parking+Pool+Gym

Jul 1 – 8

$160 per night

Destinations to explore

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