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

The median rent for a one-bedroom apartment in Winter Park, FL is $1,349, while a two-bedroom apartment averages $1,649.

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

Rents in Winter Park, FL have experienced a slight decline in 2024, with average monthly rents decreasing by 3.1% year-over-year.

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

The best time to look for an apartment in Winter Park, FL is during the less competitive months of April and January, when prices may be lower, although the selection might be limited.

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

Yes, approximately 62% of the listings in Winter Park, FL are pet-friendly with some restrictions.

Are utilities usually included in rent in Winter-Park, FL?

Only about 11% of the listings in Winter Park, FL include utilities in the rent.

Short Term Rentals in Winter Park, FL

25 rentals

2m ago

Verified

4520 Lake Gem Cir, Orlando, FL 32806

Short term | In-unit laundry | Furnished

4 beds

2 baths

$4,380

$4,123

Price drop

Apartment for rent

Top amenities

Central Heat

Dishwasher

Furnished

Garage Parking

In-Unit Laundry

3m ago

Verified

3225 Pickfair St, Orlando, FL 32803

Short term | In-unit laundry | Furnished

3 beds

2 baths

$5,748

Apartment for rent

Top amenities

Dishwasher

Furnished

Storage

Swimming Pool

Wi-Fi

6m ago

Verified

3120 Drake Dr, Lockhart, FL 32810

Short term | In-unit laundry | Furnished

3 beds

2 baths

$5,424

Apartment for rent

Top amenities

Air Conditioning

Central Heat

In-Unit Laundry

Microwave

Wi-Fi

7m ago

Verified

5379 E Kaley St, Orlando, FL 32812

Short term | In-unit laundry | Furnished

3 beds

2 baths

$4,055

Apartment for rent

Top amenities

Air Conditioning

Central Heat

In-Unit Laundry

Microwave

Oven

Wi-Fi

7m ago

Verified

1229 Berwyn Rd, Orlando, FL 32806

Short term | In-unit laundry | Furnished

Studio

1 bath

$2,435

Apartment for rent

Top amenities

Central Heat

In-Unit Laundry

Oven

Storage

Wi-Fi

7m ago

9.4

Excellent

Verified

2014 Newman Street

2014 Newman St, Orlando, FL 32803

Short term | Furnished | Assigned parking

Studio

1 bath

$2,400

Apartment for rent

Top amenities

Assigned Parking

Central Heat

Microwave

Wi-Fi

Nearby rental good for eco-living

$2,200–$2,825

Central Business District

Nearby rental good for pet owners

$2,758

Fairview Shores

7m ago

Verified

2007 Cornell Ave, Fairview Shores, FL 32789

Short term | In-unit laundry | Furnished

3 beds

2 baths

$3,467

$2,758

Price drop

Apartment for rent

Top amenities

Furnished

In-Unit Laundry

Microwave

Oven

Wi-Fi

7m ago

Verified

3120 Peel Ave, Conway, FL 32806

Short term | Furnished | Air conditioning

1 bed

1 bath

$2,362

Apartment for rent

Top amenities

Air Conditioning

Assigned Parking

Central Heat

Microwave

Wi-Fi

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7m ago

Verified

3100 Page Ave, Orlando, FL 32806

Short term | In-unit laundry | Furnished

2 beds

1 bath

$3,752

$3,639

Price drop

Apartment for rent

Top amenities

Air Conditioning

Dishwasher

Furnished

In-Unit Laundry

Oven

Wi-Fi

7m ago

Verified

2721 Raeford Rd, Conway, FL 32806

Short term | Furnished | Air conditioning

Studio

1 bath

$2,180

Apartment for rent

Top amenities

Central Heat

Furnished

Microwave

Wi-Fi

Find sweet deals near Winter Park

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

$1,070–$3,625

Goldenrod

$1,850

Maitland

$1,400

Kirkman South

$1,300

Metro West

7m ago

Verified

1221 Corbett Ln, Orlando, FL 32806

Short term | In-unit laundry | Furnished

Studio

1 bath

$2,690

Apartment for rent

Top amenities

Air Conditioning

Central Heat

Furnished

In-Unit Laundry

Wi-Fi

Liv at Winter Park Apartment Homes - Photo 1 of 1

Rent special

9h ago

9.2

Excellent

Liv at Winter Park Apartment Homes

4755 N Goldenrod Rd, Goldenrod, FL 32817

Short term | In-unit laundry | Swimming pool

Studio–3 beds

1–2 baths

$1,070–$3,625

Price drop

Apartment for rent

Available Apr 23

Top amenities

Ceiling Fan

Hardwood Floor

In-Unit Laundry

On-Site Management

Swimming Pool

Call

Highly rated

2d ago

9.2

Excellent

Verified

10200 Falcon Pine Blvd

10200 Falcon Pine Blvd, Orlando, FL 32829

Short term | Furnished

1–2 beds

1–2 baths

$2,097–$2,244

Apartment for rent

2d ago

Short Term College Park house for rent in Orlando

Beautiful Fully Furnished Lakefront Pool Home - Short Terms Available

1224 Alexandra Ct #NA, Orlando, FL 32804

Short term | In-unit laundry | Furnished

3 beds

3.5 baths

$12,000

$11,499

Price drop

House for rent

Available Jul 1

Top amenities

Assigned Parking

Dishwasher

Fitness Center

Garage Parking

In-Unit Laundry

Swimming Pool

Rent special

5d+ ago

9.2

Excellent

Verified

480 N. Orange Ave.

480 N Orange Ave, Orlando, FL 32801

Short term | Furnished

1–2 beds

1 bath

$2,200–$2,825

Apartment for rent

Rent special

5d+ ago

9.2

Excellent

Verified

2801 Biltmore Park Dr

2801 Biltmore Park Dr, Orlando, FL 32835

Short term | Furnished

1–2 beds

1–2 baths

$1,919–$2,782

Apartment for rent

5d+ ago

Short Term Lake Mann Estates apartment for rent in Orlando

Coleman

3328 Coleman Pl #A, Orlando, FL 32805

Short term | Furnished | On-site laundry

1 bed

2 baths

$1,200

Apartment for rent

Available Feb 1

Top amenities

Dishwasher

Furnished

On-Site Laundry

5d+ ago

Short Term Rock Lake house for rent in Orlando

Private room for rent in Orlando - Utilities & wifi included!

417 N Tampa Ave, Orlando, FL 32805

Short term | In-unit laundry | Furnished

1 bed

1 bath

$750

House for rent

Available Aug 18

Top amenities

Dishwasher

In-Unit Laundry

5d+ ago

Short Term Azalea Park apartment for rent in Azalea Park

Duplex - ORLANDO, FL

5838 Sage Dr, Azalea Park, FL 32807

Short term | In-unit laundry | Furnished

1 bed

1 bath

$1,450

Apartment for rent

Top amenities

Furnished

In-Unit Laundry

Tile Floor

5d+ ago

Short Term house for rent in Maitland

518 Oranole Rd, Maitland, FL 32751

Short term | Outdoor space

3 beds

1.5 baths

$2,300

House for rent

5d+ ago

Short Term Florida Center North condo for rent in Orlando

5124 Conroy Road, Orlando, FL 32811

Short term | Air conditioning | Assigned parking

1 bed

1 bath

$1,400

Condo for rent

Top amenities

Assigned Parking

5d+ ago

Short Term Golfside condo for rent in Winter Park

Short term

1 bed

1 bath

$1,299

Condo for rent

5d+ ago

Short Term Metro West condo for rent in Orlando

2511 Metro Sevilla Dr, Orlando, FL 32835

Short term | Swimming pool | Fitness center

3 beds

2 baths

$2,100

Condo for rent

5d+ ago

Short Term condo for rent in Maitland

1325 Lake Shadow Cir, Maitland, FL 32751

Short term | Air conditioning | Carpet

2 beds

2 baths

$1,850

Condo for rent

5d+ ago

Short Term condo for rent in Orlando

952 Courtyard Ln, Orlando, FL 32825

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

2 beds

2 baths

$1,700

Condo for rent

Top amenities

Carpet

In-Unit Laundry

On-Site Laundry

Showing 1 - 25 of 25 results

Home > Apartments in Winter Park > Winter Park Short term rentals

Updated: April 23, 2026

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