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Short Term Rentals in Windermere, FL

25 rentals

3121 Paradox Cir - Photo 1 of 1

18h ago

Our team has verified this company

Verified

3121 Paradox Cir, Kissimmee, FL 34746

Short term | In-unit laundry | Furnished

3 beds

2 baths

$6,123

Condo for rent

Top amenities
Central Heat
Fitness Center
Furnished
Oven
TV
Wi-Fi
4710 Sleepy Hollow Dr - Photo 1 of 1

18h ago

Our team has verified this company

Verified

4710 Sleepy Hollow Dr, Kissimmee, FL 34746

Short term | In-unit laundry | Furnished

6 beds

4 baths

$11,528

$10,763

Price drop

Apartment for rent

Top amenities
Air Conditioning
Furnished
In-Unit Laundry
Microwave
Swimming Pool
Wi-Fi
1248 1248 Challenge Drive - Photo 1 of 1

18h ago

Our team has verified this company

Verified

1248 1248 Challenge Drive, Kissimmee, FL 34747

Short term | In-unit laundry | Furnished

4 beds

3 baths

$4,021

House for rent

Top amenities
Air Conditioning
Microwave
Oven
Swimming Pool
TV
Wi-Fi
1626 Lima Ave - Photo 1 of 1

18h ago

Our team has verified this company

Verified

1626 Lima Ave, Kissimmee, FL 34747

Short term | In-unit laundry | Furnished

8 beds

6 baths

$9,246

$4,531

Price drop

Apartment for rent

Top amenities
Air Conditioning
Assigned Parking
Central Heat
In-Unit Laundry
Oven
Swimming Pool
14551 Star Water Rd - Photo 1 of 1

18h ago

Our team has verified this company

Verified

14551 Star Water Rd, Kissimmee, FL 34747

Short term | In-unit laundry | Furnished

1 bed

1 bath

$3,476

$2,472

Price drop

Apartment for rent

Top amenities
Central Heat
Elevator
Furnished
In-Unit Laundry
Oven
Wi-Fi
5885 Lakehurst Drive - Photo 1 of 1

3d ago

9.5

Excellent

Our team has verified this company

Verified

5885 Lakehurst Drive

5885 Lakehurst Dr, Orlando, FL 32819

Short term | Furnished

1–2 beds

1–2 baths

$1,917–$2,573

Apartment for rent

Nearby rental good for eco-living

$3,300

Winter Garden

Nearby rental good for pet owners

8925 Livigno Way - Photo 1 of 1

3d ago

9.2

Excellent

Our team has verified this company

Verified

8925 Livigno Way

8925 Livigno Way, Bay Lake, FL 34747

Short term | Furnished

2–3 beds

2 baths

$2,443–$2,712

Apartment for rent

2801 Biltmore Park Dr - Photo 1 of 1

3d ago

9.2

Excellent

Our team has verified this company

Verified

2801 Biltmore Park Dr

2801 Biltmore Park Dr, Orlando, FL 32835

Short term | Furnished

1–2 beds

1–2 baths

$1,744–$2,640

Apartment for rent

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9223 Vintage Hills Way - Photo 1 of 1

3d ago

9.2

Excellent

Our team has verified this company

Verified

9223 Vintage Hills Way

9223 Vintage Hills Way, Winter Garden, FL 34787

Short term | Furnished

1–2 beds

1–2 baths

$2,044–$2,620

Apartment for rent

5256 International Dr. - Photo 1 of 1

3d ago

9.2

Excellent

Our team has verified this company

Verified

5256 International Dr.

5256 International Dr, Orlando, FL 32819

Short term | Furnished

1–2 beds

1–2 baths

$2,092–$2,557

Apartment for rent

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

$3,075

Windermere

$4,500

Windermere

$2,900

Windermere

$4,500

Windermere

2053 Carolina Ave - Photo 1 of 1

4d ago

Short Term house for rent in Gotha

2053 Carolina Ave, Gotha, FL 34734

Short term | In-unit laundry | Furnished

1 bed

1 bath

$2,250

$1,800

Price drop

House for rent

Available Feb 1

Top amenities
Air Conditioning
Cable
Dishwasher
In-Unit Laundry
On-Site Laundry
10733 Village Lake Road - Photo 1 of 1

5d+ ago

Short Term townhouse for rent in Windermere

10733 Village Lake Road, Windermere, FL 34786

Short term | In-unit laundry | Garage parking

4 beds

3 baths

$3,075

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
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 | Carpet | Residents lounge

4 beds

3 baths

$3,400

House for rent

10052 Oakside Court - Photo 1 of 1

5d+ ago

Short Term house for rent in Orlando

10052 Oakside Court, Orlando, FL 32836

Short term | Swimming pool | Hardwood floor

4 beds

3 baths

$3,500

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 | Furnished | Swimming pool

5 beds

4 baths

$4,500

House for rent

Top amenities
Furnished
1339 Daniels Cove Drive - Photo 1 of 1

5d+ ago

Short Term house for rent in Winter Garden

1339 Daniels Cove Drive, Winter Garden, FL 34787

Short term | Swimming pool | Package service

3 beds

2 baths

$2,495

House for rent

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 | Garage parking | Storage

5 beds

4 baths

$4,500

House for rent

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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

5d+ ago

Short Term house for rent in Orlando

10299 Park Estates Ave, Orlando, FL 32836

Short term | Furnished | Outdoor space

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

9121 Edenshire Circle - Photo 1 of 1

5d+ ago

Short Term house for rent in Orlando

9121 Edenshire Circle, Orlando, FL 32836

Short term | In-unit laundry | On-site laundry

4 beds

3 baths

$3,200

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
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 | Furnished | Carpet

4 beds

2 baths

$3,300

House for rent

8156 Boat Hook Loop - Photo 1 of 1

5d+ ago

Short Term condo for rent in Windermere

8156 Boat Hook Loop, Windermere, FL 34786

Short term | In-unit laundry | Balcony

3 beds

2 baths

$2,200

Condo for rent

Top amenities
Fitness Center
In-Unit Laundry
Swimming Pool
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 | Carpet | Outdoor space

4 beds

2 baths

$2,750

House for rent

Showing 1 - 25 of 25 results
Home > Apartments in Windermere > Windermere Short term rentals
Updated: March 5, 2026

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1 bedrooms for rent in Windermere, FL2 rentals

2 rentals

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Looking for short term apartments in Windermere, FL near you?

🔑Available apartment rentals25
💰Best rent deal2801 Biltmore Park Dr
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