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Short Term Rentals in Windermere, FL

25 rentals

4710 Sleepy Hollow Drive - Photo 1 of 1

1d ago

Our team has verified this company

Verified

4710 Sleepy Hollow Drive, Kissimmee, FL 34746

Short term | In-unit laundry | Outdoor space

6 beds

5 baths

$6,737

$6,392

Price drop

House for rent

Top amenities
Dishwasher
Fitness Center
In-Unit Laundry
Microwave
Oven
Wi-Fi
4822 Brier Rose Lane - Photo 1 of 1

1d ago

Our team has verified this company

Verified

4822 Brier Rose Lane, Kissimmee, FL 34746

Short term | In-unit laundry | Outdoor space

5 beds

4 baths

$5,836

House for rent

Top amenities
Air Conditioning
Central Heat
Dishwasher
Fitness Center
Microwave
TV
4824 Dedication Street - Photo 1 of 1

1d ago

Our team has verified this company

Verified

4824 Dedication Street, Kissimmee, FL 34746

Short term | In-unit laundry | Outdoor space

4 beds

3 baths

$5,416

$4,541

Price drop

House for rent

Top amenities
Central Heat
Dishwasher
Furnished
In-Unit Laundry
Microwave
TV
4816 Love Storey Ln - Photo 1 of 1

1d ago

Our team has verified this company

Verified

4816 Love Storey Ln, Kissimmee, FL 34746

Short term | In-unit laundry | Outdoor space

4 beds

3 baths

$5,721

$5,368

Price drop

House for rent

Top amenities
Central Heat
Fitness Center
Furnished
In-Unit Laundry
Swimming Pool
TV
8013 Cool Breeze Dr - Photo 1 of 1

1d ago

Our team has verified this company

Verified

8013 Cool Breeze Dr, Orlando, FL 32819

Short term | In-unit laundry | Air conditioning

3 beds

3 baths

$7,657

$6,234

Price drop

House for rent

Top amenities
Air Conditioning
Business Center
In-Unit Laundry
Oven
TV
Wi-Fi
14545 Damai Lane - Photo 1 of 1

1d ago

Our team has verified this company

Verified

14545 Damai Lane, Orlando, FL 32821

Short term | In-unit laundry | Outdoor space

4 beds

3 baths

$5,584

House for rent

Top amenities
Central Heat
Dishwasher
In-Unit Laundry
Microwave
Oven
Swimming Pool

Nearby rental good for eco-living

$3,300

Winter Garden

Nearby rental good for pet owners

$1,100

Southchase

127 Pompano Beach Drive - Photo 1 of 1

2d ago

Our team has verified this company

Verified

127 Pompano Beach Drive, Kissimmee, FL 34746

Short term | In-unit laundry | Outdoor space

3 beds

3 baths

$2,567

House for rent

Top amenities
Central Heat
Fitness Center
In-Unit Laundry
Microwave
TV
Wi-Fi
8942 Cuban Palm Road - Photo 1 of 1

2d ago

Our team has verified this company

Verified

8942 Cuban Palm Road, Kissimmee, FL 34747

Short term | In-unit laundry | Outdoor space

4 beds

3 baths

$3,018

House for rent

Top amenities
Air Conditioning
Furnished
In-Unit Laundry
Microwave
TV
Wi-Fi
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5023 Windermere Avenue - Photo 1 of 1

2d ago

Our team has verified this company

Verified

5023 Windermere Avenue, Kissimmee, FL 34746

Short term | In-unit laundry | Outdoor space

5 beds

4 baths

$5,114

House for rent

Top amenities
Central Heat
Dishwasher
Fitness Center
Furnished
TV
Wi-Fi
1535 Carey Palm Circle - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1535 Carey Palm Circle, Kissimmee, FL 34747

Short term | In-unit laundry | Outdoor space

5 beds

4 baths

$6,903

$4,670

Price drop

House for rent

Top amenities
Air Conditioning
Central Heat
Dishwasher
Fitness Center
In-Unit Laundry
Swimming Pool
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Find sweet deals near Windermere

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$4,500

Windermere

$2,900

Windermere

$4,500

Windermere

$3,600

Bay Hill

2644 Reading Trail - Photo 1 of 1

4d ago

Our team has verified this company

Verified

2644 Reading Trail, Kissimmee, FL 34746

Short term | In-unit laundry | Outdoor space

5 beds

4 baths

$6,701

$6,594

Price drop

House for rent

Top amenities
Central Heat
Dishwasher
In-Unit Laundry
Oven
TV
Wi-Fi
10052 Oakside Ct - Photo 1 of 1

5d+ ago

Short Term house for rent in Orlando

10052 Oakside Ct, Orlando, FL 32836

Short term | Swimming pool | Hardwood floor

4 beds

3 baths

$3,500

House for rent

2986 Protagonist Street - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2986 Protagonist Street, Kissimmee, FL 34746

Short term | In-unit laundry | Outdoor space

4 beds

3 baths

$4,687

House for rent

Top amenities
Central Heat
Dishwasher
Furnished
In-Unit Laundry
Oven
Wi-Fi
3197 Pequod Place - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3197 Pequod Place, Kissimmee, FL 34746

Short term | In-unit laundry | Outdoor space

4 beds

3 baths

$5,188

$4,494

Price drop

House for rent

Top amenities
Fitness Center
Furnished
In-Unit Laundry
Oven
Swimming Pool
TV
8865 Della Scala Cir - Photo 1 of 1

5d+ ago

Short Term Bay Hill townhouse for rent in Bay Hill

8865 Della Scala Cir, Bay Hill, FL 32836

Short term | Residents lounge

4 beds

3 baths

$3,600

House for rent

6926 Cucamelon Ct - Photo 1 of 1

5d+ ago

Short Term house for rent in Windermere

6926 Cucamelon Ct, Windermere, FL 34786

Short term | Swimming pool | Fireplace

5 beds

4 baths

$4,500

House for rent

Top amenities
Furnished
11994 Mckinnon Rd - Photo 1 of 1

5d+ ago

Short Term house for rent in Windermere

11994 Mckinnon Rd, Windermere, FL 34786

Short term | Outdoor space | Storage

4 beds

3 baths

$4,500

House for rent

1339 Daniels Cove Dr - Photo 1 of 1

5d+ ago

Short Term house for rent in Winter Garden

1339 Daniels Cove Dr, Winter Garden, FL 34787

Short term | Outdoor space | Swimming pool

3 beds

2 baths

$2,495

House for rent

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12647 Arley Dr - Photo 1 of 1

5d+ ago

Short Term house for rent in Windermere

12647 Arley Dr, Windermere, FL 34786

Short term | Carpet

4 beds

2 baths

$2,900

House for rent

4324 Blue Major Dr - Photo 1 of 1

5d+ ago

Short Term house for rent in Windermere

4324 Blue Major Dr, Windermere, FL 34786

Short term | Outdoor space | Storage

5 beds

4 baths

$4,500

House for rent

9223 Leeland Archer Blvd - Photo 1 of 1

5d+ ago

Short Term house for rent in Orlando

9223 Leeland Archer Blvd, Orlando, FL 32836

Short term

5 beds

3 baths

$2,950

House for rent

10299 Park Estates Ave - Photo 1 of 1
New construction

5d+ ago

Short Term house for rent in Orlando

10299 Park Estates Ave, Orlando, FL 32836

Short term | Outdoor space | Furnished

3 beds

2 baths

$4,850

House for rent

6910 Corley Ave - Photo 1 of 1

5d+ ago

Short Term house for rent in Windermere

6910 Corley Ave, Windermere, FL 34786

Short term

3 beds

2 baths

$3,000

House for rent

427 Tierra Verde Ln - Photo 1 of 1

5d+ ago

Short Term house for rent in Winter Garden

427 Tierra Verde Ln, Winter Garden, FL 34787

Short term | Carpet | Furnished

4 beds

2 baths

$3,300

House for rent

9018 Lake Fischer Blvd - Photo 1 of 1

5d+ ago

Short Term house for rent in Gotha

9018 Lake Fischer Blvd, Gotha, FL 34734

Short term | Outdoor space | Carpet

4 beds

2 baths

$2,750

House for rent

Showing 1 - 25 of 25 results
Home > House Rentals in Windermere > Windermere Short term rentals
Updated: November 23, 2025

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Discover houses for rent in Windermere, FL

🌇Available house rentals25 houses
💰Best rent deal1339 Daniels Cove Dr
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