Apartments in Winter Park

1 - 30 of 87 Results
23
$878
Winter Park, FL
1 BR | Ask for Availability
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18
$882
Winter Park, FL
1 BR | Ask for Availability
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13
$840
Winter Park, FL
1 BR | Ask for Availability
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16
$1,799 - 1,999
2001 Glenridge Way Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Surface Parking
Storage
1
$2,300
2441 Fifeshire Dr Winter Park, FL
3 BR | Ask for Availability
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Dog Friendly
Cat Friendly
House
Storage
Dishwasher
30
3D Tour
$1,253 - 1,763
3114 Terry Brook Dr Winter Park, FL
1 - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Luxury
Air Conditioning
In Unit Laundry
43
3D Tour
$1,350 - 1,790
3250 Whisper Lake Lane Winter Park, FL
1 - 2 BR | Available Now
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Furnished
Dog Friendly
Cat Friendly
Virtual Tour
Luxury
36
$1,564 - 4,621
1305 Morgan Stanley Ave Winter Park, FL
Studio - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Luxury
Air Conditioning
Covered Parking
36
$1,279 - 2,880
3207 Rosebud Lane Winter Park, FL
1 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Balcony/Deck/Patio
Fitness Center
16
$1,899
3656 N Goldenrod Rd Winter Park, FL
2 BR | Feb. 20, 2026
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Dog Friendly
Cat Friendly
Storage
Disability Access
Dishwasher
82
$1,318 - 1,999
5 Autumn Breeze Way Winter Park, FL
1 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Covered Parking
Fitness Center
Storage
23
3D Tour
$1,105 - 2,075
7000 University Blvd Winter Park, FL
1 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Virtual Tour
Luxury
Air Conditioning
12
$1,449 - 1,519
220 S Semoran Boulevard Winter Park Winter Park, FL
1 BR | Available Now
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Heat Included
Dog Friendly
Cat Friendly
Virtual Tour
Air Conditioning
58
$1,249 - 1,899
3650 Summer Wind Dr Winter Park, FL
Studio - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Luxury
Air Conditioning
In Unit Laundry
32
$1,349 - 1,949
2890 Red Lion Sq Winter Park, FL
1 - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Virtual Tour
Luxury
Air Conditioning
10
$1,094 - 1,719
210 Welcome Way Fern Park, FL
Studio - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Luxury
Air Conditioning
Surface Parking
34
$1,399 - 2,099
1699 Semoran N Cir Winter Park, FL
1 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Virtual Tour
Air Conditioning
Covered Parking
18
$2,099
Winter Park, FL
3 BR | Available Now
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1
$1,690
211 Stefanik Rd Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
House
Disability Access
1
$1,600
241 Lewfield Cir Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
House
Disability Access
Dishwasher
16
$1,950
Winter Park, FL
2 BR | Available Now
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36
$4,950
Winter Park, FL
4 BR | Available Now
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1
$1,925
942 Gloriosa Ave Winter Park, FL
2 BR | Apr. 27, 2026
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Dog Friendly
Cat Friendly
House
Balcony/Deck/Patio
Storage
15
$1,320
Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
19
$1,249 - 2,085
3440 N Goldenrod Rd Winter Park, FL
1 - 3 BR | Feb. 17, 2026
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Dog Friendly
Cat Friendly
Fitness Center
Dishwasher
29
$15,550
Winter Park, FL
8+ BR | Available Now
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House
Balcony/Deck/Patio
Storage
Dishwasher
20
$3,600
Winter Park, FL
2 BR | Available Now
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14
$2,400
Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
House
Balcony/Deck/Patio
Storage
11
$1,157 - 1,392
7502 Sun Key Blvd Winter Park, FL
1 - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Fitness Center
29
$1,750
Winter Park, FL
2 BR | Available Now
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Dog Friendly
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1 - 30 of 87 Results
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How much does it cost to rent an apartment in Winter Park?

Winter Park Apartments
Bed Type Average Rent Range
Studio $1,250 $880 - $1,690
1BR $1,360 $1,030 - $1,900
2BR $1,590 $1,280 - $2,000
3BR $2,010 $1,750 - $3,660
4+BR $4,380 $2,500 - $7,000

Find a Winter Park Apartment

Part of the greater Orlando-Kissimmee-Sanford metropolitan area, Winter Park is a city of nearly 28,000. The town is a beautiful, open, sunny and green Florida paradise. The community was founded as a resort town, and even today many of the local businesses seem geared towards ensuring that the residents have their fill of rest and relaxation.

The resort atmosphere has led to several celebrities from various walks of life making their home here. The ample collection of local golf courses is perhaps what has attracted the several famous golfers that now live in Winter Park. With six post secondary institutions, the small city also has a high number of higher education options compared to its population.

When to Search

Florida is a very popular winter destination for many people that live in places that get severe weather during the cold season. As a result, many of the non-owner-occupied suites in Winter Park get rented to people who only want to live there for the winter months. If you're looking for a full time residence, you'll have much better luck shopping in summer than in the winter.

Staying in the Know

When you're renting in an apartment building, remember that you're joining a community. If you come across as someone who is loud or who likes to party, it is unlikely that you're going to get invited to join that community. If instead you can communicate that you're quiet, respectful and friendly, then the landlord is likely going to want you as his or her newest tenant.

Life in Winter Park

Transportation

Almost everyone that needs to get around further they can walk in Winter Park simply drives. The roads are well maintained and easy to drive, and parking is ample. Within the town site itself, you will likely find that you can walk most places. The great weather also means that using a bicycle as a year-round vehicle is not only practical, but common.

Where to play

Golf is of course one of the most popular local forms of entertainment. The downtown core is full of museums and quaint shops that a person could spend hours touring. There are a couple of great Italian restaurants in town including Costanzo's and Pannullo's, and many other restaurants worth exploring. For a great beer at an Irish pub, visit Fiddler's Green. If wine is more your drink, head to the Wine Room on South Park Avenue.

Neighborhoods

Search Cities Near Winter Park, FL

Campuses Nearby

Winter Park:
February Rent Report

Welcome to the February 2026 Winter Park Apartment Report. In this assessment of the local rental market, Rentable data scientists and rental experts break down the February 2026 key findings and figures for the Winter Park rental landscape.

Our experts analyze the pricing trends — one-bedroom, two-bedroom, year-over-year and month-over-month — in Winter Park and surrounding areas and provide comparisons to the entire metro area, nearby cities and some of the most desirable and expensive cities in the United States. Take a look at the last 12 months of Winter Park average rent prices in the chart below.

Monthly Rent Report

$1,800
$1,350
$900
$450
$0
Mar. 2025
Apr. 2025
May. 2025
Jun. 2025
Jul. 2025
Aug. 2025
Sep. 2025
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Jan. 2026
Feb. 2026
1 BR       2 BR

Winter Park Rent Prices Decrease From January to February

Winter Park rent prices decreased over the last month. From January to February, the city experienced a 0% decrease for the price of a one-bedroom apartment. The rent price for a Winter Park one-bedroom apartments currently stands at $.

When we take a look at the two-bedroom comparison from January to February, Winter Park experienced a 0% decrease for the price of a two-bedroom apartment. The rent price for a Winter Park two-bedroom apartments currently stands at $.

February Prices: Winter Park vs. Surrounding Areas

Rent Prices in Winter Park and Surrounding Areas

Rent prices have decreased in Winter Park over the last month. But how have the surrounding areas fared when it comes to the recent volatility in apartment prices? Rent prices in 0 of the Winter Park suburbs increased last month. On the other hand, 0 local areas experienced a decrease in the price of a one-bedroom apartment.

More key findings include:

  • Rents did not increase in any of the Winter Park suburbs

  • Rents did not decrease in any of the Winter Park suburbs.

February 2026 Pricing Trends: Winter Park vs. National Comparisons

Winter Park Rent Prices More Affordable Than Major Cities

Rent growth in Winter Park over the past year has been declining. When compared to major cities nearby, along with some of the most expensive cities in the country, Winter Park average rent prices appear to be relatively affordable for local residents.

The price for a Winter Park one-bedroom apartment remains vastly more affordable than four of the largest cities in the United States — New York City, Washington, D.C. San Francisco and Los Angeles. And pricing compares quite similarly to nearby Midwest cities.

For more information about Winter Park and surrounding area rent prices, take a look at the complete data set below.

Data set for Winter Park and suburbs

1 BR February 1 BR M/M % Change 2 BR February 2 BR M/M % Change

Methodology

Each month, using over 1 million Rentable listings across the United States, we calculate the median 1-bedroom and 2-bedroom rent prices by city, state, and nation, and track the month-over-month percent change. To avoid small sample sizes, we restrict the analysis for our reports to cities meeting minimum population and property count thresholds.