36 Best Houses for Rent in Windermere, FL | Peerspace

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Popular houses

Lakefront Home with Stunning Views

5.0 (2)

25 guests

From

$125

/hr

2 hr min

Historic Mediterranean Villa

Edgewood, Orlando, FL

5.0 (29)

150 guests

From

$110

/hr

5 hr min

Sunny Cali Casual Lakefront Home for Photo & Film | Orlando Area | Christmas Styling Nov. 1

Lake Butler, Winter Garden, FL

5.0 (56)

25 guests

From

$150

/hr

2 hr min

Lakeside Backyard

150 guests

From

$100

/hr

4 hr min

Cozy Family Home

Johnson Village, Orlando, FL

5.0 (3)

25 guests

From

$50

/hr

4 hr min

Spacious Orlando Home with Private Pool, Scenic Conservation Views & Multiple Lifestyle Sets

Orlando, FL, FL

8 guests

From

$115

/hr

2 hr min

Lakefront Vintage House in Orlando

Lake Holden Shores, Orlando, FL

25 guests

From

$250

/hr

2 hr min

Ranch Style Lake House with Dock on an Acre

Palomar, Orlando, FL

5.0 (5)

50 guests

From

$150

/hr

3 hr min

Casa Laal- 1925 Spanish Revival home in Downtown Orlando

Lake Davis/Greenwood, Orlando, FL

5.0 (1)

30 guests

From

$200

/hr

3 hr min

Sprawling Rustic-Chic Estate Minutes from Downtown Orlando

Clarcona, Orlando, FL

60 guests

From

$350

/hr

4 hr min

Grand, Expansive Club Room in Orlando

4.8 (43)

30 guests

From

$165

/hr

3 hr min

Cozy Coastal Lakefront Home

5.0 (5)

20 guests

From

$75

/hr

2 hr min

Urban Home Photo and Video Studio with Backdrops and/or Living Space

Williamsburg, Orlando, FL

5.0 (3)

10 guests

From

$130

/hr

2 hr min

Modern Luxury Spacious Home

Four Corners, Kissimmee, FL

5.0 (2)

15 guests

From

$100

/hr

4 hr min

Modern tutor home with California casual interior close to downtown

Rose Isle, Orlando, FL

5.0 (11)

25 guests

From

$150

/hr

4 hr min

Colorful Mid-Century Inspired Home with Indoor-Outdoor Spaces

Lake Como, Orlando, FL

5.0 (1)

15 guests

From

$95

/hr

2 hr min

Bright Open Concept Home with Fireplace and Chefs Kitchen

College Park, Orlando, FL

5.0 (14)

40 guests

From

$110

/hr

2 hr min

Creative Bungalow for Lifestyle Experience

6 guests

From

$85

/hr

2 hr min

Downtown, Sun-Drenched Historic Home with Modern Amenities - As Seen On ABC's 20/20!

Lake Cherokee, Orlando, FL

5.0 (2)

10 guests

From

$135

/hr

4 hr min

Ariel Pool Home W/Spa-10 Mi To Disney

Four Corners, Clermont, FL

10 guests

From

$90

/hr

1 hr min

House of Hannah Maed

College Park, Orlando, FL

5.0 (15)

6 guests

From

$75

/hr

2 hr min

Vibrant, colorful house with gorgeous porch & patio

Baldwin Park, Orlando, FL

5.0 (4)

85 guests

From

$200

/hr

4 hr min

2200sq ft home between downtown Orlando and OIA that is very roomy

Conway, Orlando, FL

20 guests

From

$75

/hr

4 hr min

Beach Themed Vacation Pool Home

Four Corners, Clermont, FL

12 guests

From

$90

/hr

3 hr min

Modern Elegance with Private Sunset Views: Join the Glow Party After dark

Four Corners, Kissimmee, FL

5 guests

From

$135

/hr

2 hr min

1970s and Boho Style Home

Southeast Orlando, FL

5.0 (3)

25 guests

From

$75

/hr

1 hr min

Vacation Villa with Private Pool

20 guests

From

$200

/hr

4 hr min

1970s Room with Multiple Set Options

Southeast Orlando, FL

15 guests

From

$55

/hr

1 hr min

Stylish Resort Villa Near Disney with Private Pool

Four Corners, Kissimmee, FL

23 guests

From

$247

/hr

3 hr min

Adorable home on corner lot in the center of Orlando

Audubon Park, Orlando, FL

5.0 (2)

10 guests

From

$200

/hr

1 hr min

Eclectic Home Where Luxury Meets Affordability

Altamonte Springs, FL

5.0 (3)

30 guests

From

$135

/hr

4 hr min

Golden Film Florida

30 guests

From

$100

/hr

3 hr min

Large 8 Bedroom Villa with Pool, Bathtub and Private Conservation Area

30 guests

From

$250

/hr

4 hr min

Mid Century Modern Home with Vegetable Patch

25 guests

From

$175

/hr

3 hr min

Vibrant Poolside Retreat w/ Game Room, Lake Views & Open Layout

7 guests

From

$139

/hr

2 hr min

Modern Tiny Home Under The Trees

15 guests

From

$100

/hr

3 hr min

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Updated October 15, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.