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Short Term Rentals in Winter Garden, FL

25 rentals

Halston Waterleigh - Photo 1 of 1
3D tour

7h ago

8.8

Very good

Halston Waterleigh

10091 Tuller Loop, Winter Garden, FL 34787

Short term | In-unit laundry | Garage parking

1–3 beds

1–2 baths

$1,725–$2,655

Apartment for rent

Available Dec 1

Top amenities
Ceiling Fan
EV Charging
Fitness Center
Hardwood Floor
In-Unit Laundry
Package Service
16200 Saint Martin Street - Photo 1 of 1

10h ago

Our team has verified this company

Verified

16200 Saint Martin Street, Clermont, FL 34714

Short term | In-unit laundry | Furnished

6 beds

4 baths

$7,021

$6,345

Price drop

Apartment for rent

Top amenities
Air Conditioning
Furnished
In-Unit Laundry
Microwave
Oven
Wi-Fi
9260 Vintage Hills Way - Photo 1 of 1

10h ago

Our team has verified this company

Verified

9260 Vintage Hills Way, Winter Garden, FL 34787

Short term | In-unit laundry | Furnished

1 bed

1 bath

$4,115

Apartment for rent

Top amenities
Dishwasher
In-Unit Laundry
Microwave
Swimming Pool
TV
Wi-Fi
1440 Retreat Circle - Photo 1 of 1

10h ago

Our team has verified this company

Verified

1440 Retreat Circle, Clermont, FL 34714

Short term | In-unit laundry | Furnished

3 beds

3 baths

$3,146

House for rent

Top amenities
Central Heat
Dishwasher
Fitness Center
Furnished
Microwave
TV
16220 Saint Martin Street - Photo 1 of 1

10h ago

Our team has verified this company

Verified

16220 Saint Martin Street, Clermont, FL 34714

Short term | In-unit laundry | Furnished

10 beds

8 baths

$13,392

$13,284

Price drop

Apartment for rent

Top amenities
Air Conditioning
Fitness Center
In-Unit Laundry
Microwave
Swimming Pool
Wi-Fi
16368 Saint Kitts Circle - Photo 1 of 1

10h ago

Our team has verified this company

Verified

16368 Saint Kitts Circle, Clermont, FL 34714

Short term | In-unit laundry | Furnished

10 beds

8 baths

$10,866

$10,086

Price drop

Apartment for rent

Top amenities
Air Conditioning
Central Heat
Fitness Center
In-Unit Laundry
Oven
Swimming Pool

Nearby rental good for eco-living

Nearby rental good for pet owners

16806 Glenbrook Boulevard - Photo 1 of 1

10h ago

Our team has verified this company

Verified

16806 Glenbrook Boulevard, Clermont, FL 34714

Short term | In-unit laundry | Furnished

4 beds

3 baths

$6,201

$5,654

Price drop

Apartment for rent

Top amenities
Garage Parking
In-Unit Laundry
Microwave
Swimming Pool
TV
Wi-Fi
9223 Vintage Hills Way - Photo 1 of 1
Rent special

2d 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 | Package service

1–2 beds

1–2 baths

$1,992–$2,553

Apartment for rent

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1436 Retreat Circle - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1436 Retreat Circle, Clermont, FL 34714

Short term | In-unit laundry | Furnished

3 beds

3 baths

$3,013

$2,849

Price drop

House for rent

Top amenities
Air Conditioning
Central Heat
Dishwasher
Swimming Pool
TV
Wi-Fi
14200 Avalon Road - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

14200 Avalon Road, Winter Garden, FL 34787

Short term | In-unit laundry | Furnished

3 beds

2 baths

$2,464

Condo for rent

Top amenities
Dishwasher
In-Unit Laundry
Oven
Swimming Pool
TV
Wi-Fi
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Find sweet deals near Winter Garden

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

$1,725–$1,825

Winter Garden

$1,992–$2,164

Winter Garden

$2,464

Winter Garden

$3,700

Winter Garden

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
17361 Bal Harbour Dr - Photo 1 of 1

5d+ ago

Short Term house for rent in Winter Garden

17361 Bal Harbour Dr, Winter Garden, FL 34787

Short term | Garage parking | On-site laundry

4 beds

3 baths

$3,400

House for rent

Top amenities
On-Site Laundry
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 | 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

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 baths

$4,800

House for rent

Top amenities
On-Site Laundry
Package Service
Swimming Pool
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

7254 Desert Mandarin 7254 - Photo 1 of 1

5d+ ago

Short Term house for rent in Winter Garden

Single Family Residence - Other City - In The State Of Florida, FL

7254 Desert Mandarin 7254, Winter Garden, FL 34787

Short term | Walk-in closets | Outdoor space

5 beds

3 baths

$3,700

House for rent

7984 Wood Sage Dr - Photo 1 of 1

5d+ ago

Short Term house for rent in Winter Garden

7984 Wood Sage Dr, Winter Garden, FL 34787

Short term | In-unit laundry | Swimming pool

3 beds

2 baths

$3,100

House for rent

Top amenities
Fitness Center
Hardwood Floor
In-Unit Laundry
Advertisement
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 baths

$2,675

House for rent

Top amenities
Garage Parking
High Ceilings
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 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 baths

$2,500

House for rent

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

5d+ ago

Short Term house for rent in Winter Garden

11055 Folklore St, Winter Garden, FL 34787

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

4 beds

3 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

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 baths

$2,600

House for rent

8096 Sayings Dr - Photo 1 of 1
New construction

5d+ ago

Short Term house for rent in Winter Garden

8096 Sayings Dr, Winter Garden, FL 34787

Short term | Outdoor space

4 beds

4 baths

$3,750

House for rent

Showing 1 - 25 of 25 results
Home > Apartments in Winter Garden > Winter Garden Short term rentals
Updated: December 1, 2025

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

🔑Available apartment rentals25
💰Best rent deal10091 Tuller Loop
✨Popular amenities, ,

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