Apartments in Winter Park

1 - 30 of 80 Results
40
Overspin Dr Apartment for rent in Winter Park, FL
Overspin Dr Apartment for rent in Winter Park, FL
$1,015
Winter Park, FL
1 BR | Ask for Availability
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1
Sugarwood Cir Apartment for rent in Winter Park, FL
$792
Winter Park, FL
1 BR | Ask for Availability
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16
Tuscany Villas Apartment for rent in Winter Park, FL
Tuscany Villas Apartment for rent in Winter Park, FL
$1,799
3656 N Goldenrod Rd Winter Park, FL
2 BR | May. 30, 2025
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22
The Lofts Of Winter Park Village Apartment for rent in Winter Park, FL
The Lofts Of Winter Park Village Apartment for rent in Winter Park, FL
$1,625 - 1,950
520 N Orlando Ave Winter Park, FL
1 BR | Available Now
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11
Sapphire Winter Park Apartment for rent in Winter Park, FL
Sapphire Winter Park Apartment for rent in Winter Park, FL
$1,399 - 2,589
1699 Semoran N Cir Winter Park, FL
1 - 3 BR | Available Now
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17
3D Tour
Whisper Lake Apartments Apartment for rent in Winter Park, FL
Whisper Lake Apartments Apartment for rent in Winter Park, FL
$1,450 - 1,790
3250 Whisper Lake Lane Winter Park, FL
1 - 2 BR | Available Now
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Furnished
Dog Friendly
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Luxury
14
Advenir at Magnolia Apartment for rent in Fern Park, FL
Advenir at Magnolia Apartment for rent in Fern Park, FL
$1,099 - 1,782
210 Welcome Way Fern Park, FL
Studio - 2 BR | Available Now
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5
Indigo Winter Park Apartment for rent in Winter Park, FL
Indigo Winter Park Apartment for rent in Winter Park, FL
$1,349 - 1,449
220 S Semoran Boulevard Winter Park Winter Park, FL
1 BR | Available Now
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Heat Included
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37
Summerlin At Winter Park Apartments Apartment for rent in Winter Park, FL
Summerlin At Winter Park Apartments Apartment for rent in Winter Park, FL
$1,284 - 2,693
3207 Rosebud Lane Winter Park, FL
1 - 3 BR | Available Now
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8
Azure Winter Park Apartment for rent in Winter Park, FL
Azure Winter Park Apartment for rent in Winter Park, FL
$1,319 - 2,439
3650 Summer Wind Dr Winter Park, FL
Studio - 3 BR | Available Now
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23
3D Tour
Central Place At Winter Park Apartment for rent in Winter Park, FL
Central Place At Winter Park Apartment for rent in Winter Park, FL
$1,355 - 2,065
7000 University Blvd Winter Park, FL
1 - 3 BR | Available Now
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16
The Fisher Apartment for rent in Winter Park, FL
The Fisher Apartment for rent in Winter Park, FL
$1,799
2001 Glenridge Way Winter Park, FL
1 - 2 BR | Available Now
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14
Serena Winter Park Apartment for rent in Winter Park, FL
Serena Winter Park Apartment for rent in Winter Park, FL
$1,379 - 2,029
2890 Red Lion Sq Winter Park, FL
1 - 2 BR | Available Now
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7
347 Scottsdale Sq Unit 347 Apartment for rent in Winter Park, FL
347 Scottsdale Sq Unit 347 Apartment for rent in Winter Park, FL
$1,425
Winter Park, FL
1 BR | Available Now
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Dog Friendly
Air Conditioning
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9
1523 Pickwood Ave Apartment for rent in Fern Park, FL
1523 Pickwood Ave Apartment for rent in Fern Park, FL
$1,795
Fern Park, FL
2 BR | Available Now
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Dog Friendly
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House
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11
Solis at Winter Park Apartment for rent in Winter Park, FL
Solis at Winter Park Apartment for rent in Winter Park, FL
$1,289 - 1,792
7502 Sun Key Blvd Winter Park, FL
1 - 2 BR | Available Now
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Dog Friendly
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18
7637 Aloma Pines Ct Apartment for rent in Winter Park, FL
7637 Aloma Pines Ct Apartment for rent in Winter Park, FL
$2,395
Winter Park, FL
3 BR | Available Now
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House
9
1716 Miller Ave Apartment for rent in Winter Park, FL
1716 Miller Ave Apartment for rent in Winter Park, FL
$1,995
Winter Park, FL
2 BR | Apr. 1, 2025
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House
33
$1,100
Winter Park, FL
3 BR | Available Now
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Orwin Manor
1
$3,800
1096 Azalea Ln Winter Park, FL
3 BR | Jun. 1, 2025
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Disability Access
1
$3,100
644 N Knowles Ave Winter Park, FL
3 BR | Jun. 1, 2025
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Storage
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Pool
Downtown Winter Park
1
$1,695
7474 Canford Ct Winter Park, FL
2 BR | Available Now
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Surface Parking
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19
$2,000
Winter Park, FL
3 BR | Apr. 1, 2025
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Dog Friendly
Storage
Dishwasher
1
$1,695
Winter Park, FL
2 BR | May. 1, 2025
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14
$3,400
Winter Park, FL
3 BR | Available Now
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Dog Friendly
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Storage
Dishwasher
1
$1,695
Winter Park, FL
2 BR | Available Now
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Dog Friendly
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11
$1,595
Winter Park, FL
2 BR | Available Now
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1
$1,200
7341 Daniel Webster Dr #d Winter Park, FL
1 BR | Apr. 2, 2025
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Storage
Pool
1
$1,900
2611 Antilles Dr Winter Park, FL
3 BR | Available Now
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1
$1,575
7340 Swallow St Winter Park, FL
2 BR | Available Now
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1 - 30 of 80 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 $1,100 $880 - $1,340
1BR $1,380 $1,060 - $1,700
2BR $1,700 $1,420 - $2,000
3BR $2,200 $1,610 - $4,320
4+BR $2,600 $2,200 - $8,500

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:
March Rent Report

Welcome to the March 2025 Winter Park Apartment Report. In this assessment of the local rental market, Rentable data scientists and rental experts break down the March 2025 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
Apr. 2024
May. 2024
Jun. 2024
Jul. 2024
Aug. 2024
Sep. 2024
Oct. 2024
Nov. 2024
Dec. 2024
Jan. 2025
Feb. 2025
Mar. 2025
1 BR       2 BR

Winter Park Rent Prices Decrease From February to March

Winter Park rent prices decreased over the last month. From February to March, the city experienced a -1.0% decrease for the price of a one-bedroom apartment. The rent price for a Winter Park one-bedroom apartments currently stands at $1,383.0.

When we take a look at the two-bedroom comparison from February to March, Winter Park experienced a -0.3% decrease for the price of a two-bedroom apartment. The rent price for a Winter Park two-bedroom apartments currently stands at $1,664.0.

March 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.

March 2025 Pricing Trends: Winter Park vs. National Comparisons

New York, NY
San Francisco, CA
Los Angeles, CA
Washington, DC
Chicago, IL
Columbus, OH
Minneapolis, MN
Pittsburgh, PA
$4,076
$3,129
$2,387
$2,328
$1,905
$1,262
$1,247
$1,197
$0
$1,350
$2,700
$4,050
$5,400
Median Rent

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 March 1 BR M/M % Change 2 BR March 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.