Apartments in Winter Park

91 - 119 of 119 Results
1
$2,395
2037 Canny Cv Winter Park, FL
3 BR | Available Now
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Storage
Pool
11
$3,800
Winter Park, FL
4 BR | Available Now
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9
$2,100
Winter Park, FL
2 BR | Available Now
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Downtown Winter Park
16
$1,345
Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
1
$2,500
929 Dupont Ave Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
Hidden Pond
1
$2,350
7323 W Antietam Ct Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
Dishwasher
1
$1,995
931 Cypress Ave Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
1
$2,200
313 Granada Dr Winter Park, FL
4 BR | Available Now
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Dog Friendly
Cat Friendly
House
1
$2,195
Winter Park, FL
3 BR | Available Now
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Dog Friendly
House
1
$1,575
2936 Antique Oaks Cir #71 Winter Park, FL
20+ BR | Available Now
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Dog Friendly
Pool
$1,224
, FL
Studio | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
In Unit Laundry
Balcony/Deck/Patio
1
$1,300
3000 3098 Oaks Cir Winter Park, FL
1 BR | Available Now
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1
$1,750
650 Trinidad Ct Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
House
Dishwasher
Pool
1
$2,395
Winter Park, FL
3 BR | Jan. 10, 2026
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Dog Friendly
Cat Friendly
House
1
$2,040
1308 S Pennsylvania Ave Winter Park, FL
1 BR | Available Now
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Cat Friendly
Dishwasher
1
$2,595
447 N Phelps Ave Winter Park, FL
3 BR | Available Now
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Cat Friendly
House
Dishwasher
1
$1,795
918 Gloriosa Ave Winter Park, FL
3 BR | Available Now
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House
1
$2,350
1005 Bradford Dr Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
Balcony/Deck/Patio
Dishwasher
1
$1,995
Winter Park, FL
3 BR | Available Now
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Storage
1
$3,295
1807 N Park Ave Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
1
$1,195 - 1,470
600 N Semoran Blvd Winter Park, FL
1 - 2 BR | Available Now
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15
$1,010 - 1,680
311 N Knowles Ave Winter Park, FL
Studio - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Section 8
Air Conditioning
Covered Parking
$1,275 - 1,655
7745 Brandywood Cir Winter Park, FL
1 - 2 BR | Available Now
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20
$880 - 1,480
2400 Howell Branch Road Winter Park, FL
Studio - 3 BR | Ask for Availability
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Dog Friendly
Cat Friendly
Air Conditioning
Surface Parking
Balcony/Deck/Patio
7
$2,198
Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
Storage
Dishwasher
5
$1,200
Winter Park, FL
2 BR | Ask for Availability
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$1,020 - 1,635
2000 Village Ln Winter Park, FL
1 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Covered Parking
Balcony/Deck/Patio
$2,250
Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
Storage
Dishwasher
1
$1,295
3035 George Mason Ave Apt C Winter Park, FL
1 BR | Available Now
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Dishwasher
91 - 119 of 119 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 $1,260 $880 - $1,830
1BR $1,300 $1,150 - $2,060
2BR $1,600 $1,380 - $2,040
3BR $2,130 $1,770 - $3,310
4+BR $3,150 $2,200 - $4,950

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

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Winter Park:
December Rent Report

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

Winter Park Rent Prices Decrease From November to December

Winter Park rent prices decreased over the last month. From November to December, 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 November to December, 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 $.

December 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.

December 2025 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 December 1 BR M/M % Change 2 BR December 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.