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Short Term Rentals in Winter Garden, FL

25 rentals

11564 Mizzon Dr - Photo 1 of 1

5d+ ago

Short Term condo for rent in Windermere

Short term | In-unit laundry | Swimming pool

3 beds

2 baths

$2,450

Condo for rent

Top amenities
Elevator
Fitness Center
In-Unit Laundry
2729 Sweet Acacia Dr - Photo 1 of 1
New construction

5d+ ago

Short Term house for rent in Clermont

2729 Sweet Acacia Dr, Clermont, FL 34711

Short term | Furnished | Garage parking

4 beds

3 baths

$3,500

$2,850

Price drop

House for rent

Top amenities
Swimming Pool
1641 Fallmonte Ct - Photo 1 of 1

5d+ ago

Short Term townhouse for rent in Ocoee

1641 Fallmonte Ct, Ocoee, FL 34761

Short term | In-unit laundry | Garage parking

3 beds

2.5 baths

$2,200

House for rent

Top amenities
In-Unit Laundry
16652 Rialto Dr - Photo 1 of 1

5d+ ago

Short Term house for rent in Winter Garden

Resort style living close to area attractions

16652 Rialto Dr, Winter Garden, FL 34787

Short term | In-unit laundry | Furnished

3 beds

2 baths

$2,350

House for rent

Available May 1

Top amenities
Dishwasher
Fitness Center
In-Unit Laundry
Microwave
Swimming Pool
4572 Barbados Loop - Photo 1 of 1

5d+ ago

Short Term Southern Fields house for rent in Clermont

4572 Barbados Loop, Clermont, FL 34711

Short term | Carpet | Outdoor space

5 beds

3 baths

$2,800

House for rent

5518 Thomas Square Drive - Photo 1 of 1

5d+ ago

Short Term house for rent in Winter Garden

5518 Thomas Square Drive, Winter Garden, FL 34787

Short term | Garage parking | On-site laundry

5 beds

4.5 baths

$3,450

House for rent

Top amenities
Garage Parking
On-Site Laundry
Storage
Swimming Pool

Nearby rental good for eco-living

Nearby rental good for pet owners

$3,279

14200 Avalon Rd

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

2.5 baths

$2,900

House for rent

14005 Peach Orchard Way - Photo 1 of 1

5d+ ago

Short Term house for rent in Winter Garden

14005 Peach Orchard Way, Winter Garden, FL 34787

Short term | On-site laundry | Swimming pool

5 beds

3.5 baths

$4,800

House for rent

Top amenities
Concierge Service
On-Site Laundry
Package Service
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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

4.5 baths

$4,500

House for rent

10733 Village Lake Rd - Photo 1 of 1

5d+ ago

Short Term townhouse for rent in Windermere

10733 Village Lake Rd, Windermere, FL 34786

Short term | In-unit laundry | Garage parking

4 beds

3.5 baths

$3,475

House for rent

Top amenities
Concierge Service
Garage Parking
In-Unit Laundry
On-Site Laundry
Package Service
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Find sweet deals near Winter Garden

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

$1,427–$7,809

Winter Garden

$2,350

Winter Garden

$3,450

Winter Garden

$2,800

Winter Garden

6165 Juneberry Way - Photo 1 of 1

5d+ ago

Short Term townhouse for rent in Winter Garden

6165 Juneberry Way, Winter Garden, FL 34787

Short term | Garage parking | Swimming pool

3 beds

2.5 baths

$2,675

House for rent

Top amenities
High Ceilings
Storage
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

4460 Linwood Trace Lane - Photo 1 of 1

5d+ ago

Short Term house for rent in Clermont

4460 Linwood Trace Lane, Clermont, FL 34711

Short term | Garage parking | On-site laundry

4 beds

3 baths

$3,925

House for rent

Top amenities
On-Site Laundry
Swimming Pool
3230 Fawnwood Dr - Photo 1 of 1

5d+ ago

Short Term Forestbrooke house for rent in Ocoee

3230 Fawnwood Dr, Ocoee, FL 34761

Short term | Air conditioning

4 beds

3.5 baths

$3,300

House for rent

14791 Crimson Bluff Aly - Photo 1 of 1

5d+ ago

Short Term house for rent in Winter Garden

14791 Crimson Bluff Aly, Winter Garden, FL 34787

Short term | Garage parking | Swimming pool

3 beds

2.5 baths

$2,900

House for rent

11007 Bookmark Ln - Photo 1 of 1

5d+ ago

Short Term townhouse for rent in Winter Garden

11007 Bookmark Ln, Winter Garden, FL 34787

Short term | In-unit laundry | Garage parking

3 beds

2.5 baths

$2,500

House for rent

Top amenities
In-Unit Laundry
11055 Folklore Street - Photo 1 of 1

5d+ ago

Short Term house for rent in Winter Garden

11055 Folklore Street, Winter Garden, FL 34787

Short term | In-unit laundry | Walk-in closets

4 beds

3.5 baths

$2,800

House for rent

Top amenities
In-Unit 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

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13127 Bounty Ave - Photo 1 of 1

5d+ ago

Short Term townhouse for rent in Winter Garden

13127 Bounty Ave, Winter Garden, FL 34787

Short term | Swimming pool | Fitness center

3 beds

2.5 baths

$2,600

House for rent

15633 Signature Dr - Photo 1 of 1

5d+ ago

Short Term Signature Lakes house for rent in Horizon West

15633 Signature Dr, Horizon West, FL 34787

Short term | In-unit laundry | Garage parking

3 beds

2 baths

$2,850

House for rent

Top amenities
Carpet
In-Unit Laundry
13550 Laranja Street - Photo 1 of 1

5d+ ago

Short Term house for rent in Clermont

13550 Laranja Street, Clermont, FL 34711

Short term | In-unit laundry | Air conditioning

4 beds

2 baths

$2,850

House for rent

Top amenities
In-Unit Laundry
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
8096 Sayings Drive - Photo 1 of 1
New construction

5d+ ago

Short Term house for rent in Winter Garden

8096 Sayings Drive, Winter Garden, FL 34787

Short term | Outdoor space

4 beds

4 baths

$3,750

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 | Carpet | Outdoor space

4 beds

2 baths

$2,750

House for rent

4495 Harts Cove Way - Photo 1 of 1

5d+ ago

Short Term Hartwood Reserve house for rent in Clermont

4495 Harts Cove Way, Clermont, FL 34711

Short term | Swimming pool | Hardwood floor

5 beds

3.5 baths

$3,750

House for rent

Top amenities
Concierge Service
Hardwood Floor
On-Site Management
Swimming Pool
Showing 1 - 25 of 25 results
Home > Apartments in Winter Garden > Winter Garden Short term rentals
Updated: April 16, 2026

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Looking for short term apartments in Winter Garden, FL near you?

🔑Available apartment rentals25
💰Best rent deal8156 Boat Hook Loop
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