How much is the average rent in Winter Garden, FL for 1-bedroom and 2-bedroom apartments?

Winter Garden's 2025 rental market shows 1-bedroom apartments averaging around $1,800 per month, while 2-bedroom units average around $2,300 monthly. Both bedroom types experienced increases from the previous year, with 2-bedrooms seeing stronger growth at 5.3% compared to 1-bedrooms at 1.4%.

Are rents going up or down in Winter-Garden, FL?

Rents in Winter Garden, FL have experienced a relatively stable trend with a modest 0.19% year-over-year increase. Specifically, 1-bedroom rents have decreased by 1.68%, while 2-bedroom rents have increased by 1.12%.

When is the best time to look for an apartment in Winter Garden, FL?

October offers the lowest rental prices in Winter Garden, while December sees the highest rent with approximately a 3% difference between peak and off-peak pricing. August and November show less competition with reduced demand compared to supply, while March and April are the most competitive months for apartment hunting.

What are the best neighborhoods to rent an apartment in Winter Garden, FL?

Tucker Oaks and Stoneybrook West represent Winter Garden's most in-demand rental areas, generating higher consumer interest despite comprising just 3% of the total rental market. Courtlea Oaks, Tucker Oaks, and Stoneybrook West offer strong community connections with high walk scores and well-developed street infrastructure that encourage neighborhood interaction.

Are there pet-friendly apartments in Winter Garden, FL?

Winter Garden's rental market centers on pet-friendly living, with Tucker Oaks particularly accommodating for pet owners. The neighborhood offers comprehensive pet amenities including pet waste stations, dedicated pet spaces, and pet events that build community among animal lovers, while maintaining no breed restrictions.

Are utilities usually included in rent in Winter Garden, FL?

Utilities are rarely included in Winter Garden rental properties, appearing in less than 1% of total listings across all apartment types. One-bedroom apartments have the highest rate of utility inclusion at 0.14% of listings, while studios, two-bedrooms, and three-bedrooms each include utilities in fewer than 0.02% of available properties.

Luxury Apartments for Rent in Winter Garden, FL

31 rentals

New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17822 Adrift Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$5,200

House for rent

Top amenities

Dishwasher

Garage Parking

In-Unit Laundry

Swimming Pool

5d+ ago

Luxury house for rent in Winter Garden

203 S Main St, Winter Garden, FL 34787

Luxury | On-site management | Package service

2 beds

2 baths

$2,699

House for rent

Available Jul 15

Top amenities

On-Site Management

5d+ ago

Luxury house for rent in Winter Garden

16710 Point Rock Dr, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

3 beds

2.5 baths

$3,000

House for rent

Top amenities

Dishwasher

Garage Parking

In-Unit Laundry

Microwave

Swimming Pool

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

15205 Shonan Gold Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

3.5 baths

$3,400

House for rent

Top amenities

Dishwasher

Furnished

Garage Parking

In-Unit Laundry

5d+ ago

Luxury house for rent in Winter Garden

15532 Sweet Orange Ave, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2.5 baths

$3,950

House for rent

Available May 7

Top amenities

Ceiling Fan

In-Unit Laundry

On-Site Management

5d+ ago

Luxury condo for rent in Winter Garden

1300 Eastern Pecan #107 LO - 1

1300 Eastern Pecan Pl #1, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

2 beds

2 baths

$1,995

Condo for rent

Available May 1

Top amenities

Air Conditioning

Central Heat

Fitness Center

In-Unit Laundry

Residents Lounge

Swimming Pool

Nearby rental good for eco-living

$1,695

203 N Dillard St #5

Nearby rental good for pet owners

$1,605–$2,715

16200 Ascend Village Ln

New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

16350HVS

16350 Hamlin View St, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2.5 baths

$3,000

House for rent

Top amenities

In-Unit Laundry

On-Site Laundry

5d+ ago

Luxury apartment for rent in Winter Garden

Modern 1 Bed/1 Bath Unit in Winter Garden, FL - Available $1695/mo

203 N Dillard St #5, Winter Garden, FL 34787

Luxury | Air conditioning | Carpet

1 bed

1 bath

$1,695

Apartment for rent

Available May 11

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5d+ ago

Luxury apartment for rent in Winter Garden

Downtown Winter Garden Apartment one block from the shops

203 N Dillard St #4, Winter Garden, FL 34787

Luxury | Assigned parking | Hardwood floor

1 bed

1 bath

$1,495

Apartment for rent

Available May 1

417 Southern Pecan Cir #202 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Garden

1 bed 1 bath condo w/DEN in Winter Garden

417 Southern Pecan Cir #202, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

1 bed

1 bath

$1,475

Condo for rent

Top amenities

Air Conditioning

Carpet

Dishwasher

In-Unit Laundry

Find sweet deals in Winter Garden

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

$1,427–$4,057

10091 Tuller Loop

$1,495

203 N Dillard St #4

$1,475

417 Southern Pecan Cir #202

$1,550

1301 Eastern Pecan Pl

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

216 Deepcove Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

2 beds

2.5 baths

$2,300

$2,200

Price drop

House for rent

Top amenities

Ceiling Fan

Dishwasher

Garage Parking

In-Unit Laundry

On-Site Laundry

Storage

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

11153 Green Citron Aly, Winter Garden, FL 34787

Luxury | In-unit laundry | Garage parking

3 beds

2.5 baths

$3,350

$3,100

Price drop

House for rent

Top amenities

Garage Parking

In-Unit Laundry

5d+ ago

Luxury condo for rent in Winter Garden

1301 Eastern Pecan Pl, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

1 bed

1 bath

$1,550

Condo for rent

Top amenities

Controlled Access

Dishwasher

In-Unit Laundry

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

6460 Makrut Lime Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

3.5 baths

$4,250

House for rent

Top amenities

Dishwasher

Garage Parking

In-Unit Laundry

New construction

5d+ ago

Luxury house for rent in Winter Garden

Private Pond View Home in Waterleigh - 4BR + Guest Suite, No Rear Neighbors

18386 Oliver Twist Way, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

4 beds

3 baths

$4,300

House for rent

Available Jun 1

Top amenities

Dishwasher

Furnished

High Ceilings

In-Unit Laundry

Microwave

Swimming Pool

New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

15363 Hamlin Park Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

3.5 baths

$3,500

House for rent

Top amenities

Carpet

Garage Parking

In-Unit Laundry

New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

12506 Westhaven Oak Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

1 bed

1 bath

$1,600

House for rent

Top amenities

Dishwasher

In-Unit Laundry

430 Southern Pecan Cir #101 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

430 Southern Pecan Cir #101, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

2 beds

2 baths

$2,000

Condo for rent

Top amenities

Fitness Center

In-Unit Laundry

Storage

Swimming Pool

5d+ ago

Luxury house for rent in Winter Garden

Spacious 3 Bed/2 Bath Single Family Home in Winter Garden, FL - Available 4/15 - $3100

238 N Main St, Winter Garden, FL 34787

Luxury | Balcony | In-unit laundry

3 beds

2 baths

$3,100

House for rent

Available Apr 15

Top amenities

Dishwasher

In-Unit Laundry

Microwave

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

149 S Park Ave, Winter Garden, FL 34787

Luxury | Balcony | Walk-in closets

3 beds

3.5 baths

$5,200

House for rent

Top amenities

Ceiling Fan

Dishwasher

Garage Parking

High Ceilings

In-Unit Laundry

On-Site Laundry

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16242 Outlook Shore Aly, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2.5 baths

$2,990

House for rent

Top amenities

Carpet

Dishwasher

Fitness Center

High Ceilings

In-Unit Laundry

On-Site Laundry

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

15060 Andrew Aly, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

3.5 baths

$3,300

House for rent

Top amenities

Garage Parking

In-Unit Laundry

5d+ ago

Luxury Stoneybrook West townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

1220 Priory Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2.5 baths

$3,000

House for rent

Top amenities

Dishwasher

Garage Parking

In-Unit Laundry

Swimming Pool

5d+ ago

Luxury house for rent in Winter Garden

9240 Woodcrane Dr, Winter Garden, FL 34787

Luxury | In-unit laundry | Air conditioning

5 beds

4 baths

$5,499

House for rent

Top amenities

Air Conditioning

Ceiling Fan

Central Heat

Garage Parking

In-Unit Laundry

Microwave

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17552 Lake Star Rd, Winter Garden, FL 34787

Luxury | In-unit laundry | Garage parking

4 beds

3.5 baths

$4,500

House for rent

Top amenities

Carpet

Garage Parking

In-Unit Laundry

New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

7556 John Hancock Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

6.5 baths

$18,000

House for rent

Top amenities

Furnished

Garage Parking

High Ceilings

In-Unit Laundry

Residents Lounge

7054 7054 BROOMSHEDGE TRAIL TRAIL - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

7054 7054 BROOMSHEDGE TRAIL TRAIL, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

2 beds

2.5 baths

$2,280

House for rent

Top amenities

Dishwasher

Garage Parking

High Ceilings

In-Unit Laundry

Swimming Pool

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

14931 Lebeau Loop, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

3.5 baths

$5,400

House for rent

Top amenities

Fitness Center

Garage Parking

In-Unit Laundry

Storage

Swimming Pool

16324 Silver Grove Blvd #1 - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

16324 Silver Grove Boulevard - 1

16324 Silver Grove Blvd #1, Winter Garden, FL 34787

Luxury | Swimming pool | Outdoor space

5 beds

4.5 baths

$5,500

House for rent

Available Jan 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16771 Turtle Hatch Dr #D, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

3.5 baths

$4,500

House for rent

Top amenities

Ceiling Fan

Garage Parking

In-Unit Laundry

14676 Seton Creek Boulevard - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

14676 Seton Creek Boulevard, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2.5 baths

$3,000

House for rent

Top amenities

In-Unit Laundry

On-Site Laundry

Showing 1 - 31 of 31 results

Home > Apartments in Winter Garden > Winter Garden Luxury Apartments For Rent

Updated: May 14, 2026

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