Apartments in Winter Park

61 - 89 of 89 Results
1
Spacious Condo Living In Winter Park – Perfect For Families! Apartment for rent in Winter Park, FL
$1,500
1000 S Semoran Blvd Winter Park, FL
2 BR | Available Now
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1
1000 Lake of the Woods H-101 Apartment for rent in Fern Park, FL
$1,499
Fern Park, FL
2 BR | Available Now
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Pool
1
Beautiful 2 Bed / 2 Bath Condo For Rent In Downtown Winter Park! Apartment for rent in Winter Park, FL
$2,800
644 N Knowles Ave #10 Winter Park, FL
2 BR | Jun. 1, 2025
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Downtown Winter Park
1
3651 N Goldenrod #E109 Apartment for rent in Winter Park, FL
$1,600
Winter Park, FL
2 BR | Available Now
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1
Modern Luxury In Winter Park Apartment for rent in Winter Park, FL
$4,150
830 W Canton Ave Winter Park, FL
3 BR | Available Now
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1
Stunning Estate, With Luxury Upgrades, Backyard Oasis, 4B In Desirable Winter Park Florida! Apartment for rent in Winter Park, FL
$8,500
1731 Windsor Dr Winter Park, FL
4 BR | Available Now
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1
2 Bedroom Winter Park Condo For Rent, Near Full Sail & Ucf! Apartment for rent in Winter Park, FL
$1,600
3651 N Goldenrod Rd #208 Winter Park, FL
2 BR | Available Now
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1
Charming 4br/2ba Winter Park Home! Apartment for rent in Winter Park, FL
$2,395
2816 Cady Way Winter Park, FL
4 BR | Available Now
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1
Charming 3 Bed/2 Bath Home For Rent In The Beautiful Winter Park! Rollins Students Welcomed! Apartment for rent in Winter Park, FL
$3,150
5334 Lake Howell Rd Winter Park, FL
3 BR | Jun. 1, 2025
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1
Cozy Comfort! Apartment for rent in Winter Park, FL
$1,200
3069 Aaron Burr Ave Apt D Winter Park, FL
1 BR | Available Now
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1
3107 Ash Park Loop Apartment for rent in Winter Park, FL
$2,995
Winter Park, FL
3 BR | Available Now
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1
Beautiful Updated 3/2 Home In Winter Park! Apartment for rent in Winter Park, FL
$2,290
2158 Sussex Rd Winter Park, FL
3 BR | Available Now
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1
Charming 3-bedroom Home Perfect For Modern Family Living In Winter Park! Washer & Dryer Included! Apartment for rent in Winter Park, FL
$1,950
3135 Black Pine Ave Winter Park, FL
3 BR | Available Now
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1
Indiana Ave Apartment for rent in Winter Park, FL
$2,100
2032 Indiana Ave Winter Park, FL
2 BR | Available Now
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1
Beautifully Renovated Condo In The Heart Of Winter Park Apartment for rent in Winter Park, FL
$1,750
2500 Lee Rd Winter Park, FL
2 BR | Available Now
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1
Charming 4 Bedrooms, 2 Baths Pool Home Located In Winter Park! Apartment for rent in Winter Park, FL
$2,300
3445 Bowman Dr Winter Park, FL
4 BR | Ask for Availability
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1
Fabulous & Furnished In Winter Park! Apartment for rent in Winter Park, FL
$3,400
1850 Whitehall Dr Winter Park, FL
3 BR | Available Now
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Pool
$1,275 - 1,655
7745 Brandywood Cir Winter Park, FL
1 - 2 BR | Available Now
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$1,195 - 1,470
600 N Semoran Blvd Winter Park, FL
1 - 2 BR | Available Now
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19
Stonecastle Apartments Apartment for rent in Winter Park, FL
Stonecastle Apartments Apartment for rent in Winter Park, FL
$1,531 - 2,368
2015 New Stonecastle Terrace Winter Park, FL
1 - 2 BR | Available Now
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Section 8
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18
Cranes Landing Apartments Apartment for rent in Winter Park, FL
Cranes Landing Apartments Apartment for rent in Winter Park, FL
$1,520 - 2,270
3440 N Goldenrod Rd Winter Park, FL
1 - 3 BR | Available Now
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7
$2,198
Winter Park, FL
3 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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15
$1,010 - 1,680
311 N Knowles Ave Winter Park, FL
Studio - 2 BR | Available Now
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Section 8
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Covered Parking
13
$2,545 - 2,575
Winter Park, FL
3 BR | Available Now
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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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Covered Parking
Balcony/Deck/Patio
$2,250
Winter Park, FL
3 BR | Available Now
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$1,295
3035 George Mason Ave Apt C Winter Park, FL
1 BR | Available Now
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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 $1,210 $880 - $1,500
1BR $1,400 $1,140 - $1,690
2BR $1,700 $1,350 - $1,960
3BR $2,200 $1,640 - $4,110
4+BR $2,400 $2,300 - $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:
April Rent Report

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

Winter Park Rent Prices Increase From March to April

Winter Park rent prices increased over the last month. From March to April, the city experienced a 0.72% increase for the price of a one-bedroom apartment. The rent price for a Winter Park one-bedroom apartments currently stands at $1,393.0.

When we take a look at the two-bedroom comparison from March to April, Winter Park experienced a 0.66% increase for the price of a two-bedroom apartment. The rent price for a Winter Park two-bedroom apartments currently stands at $1,675.0.

April Prices: Winter Park vs. Surrounding Areas

Rent Prices in Winter Park and Surrounding Areas

Rent prices have increased 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.

April 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
$4,079
$3,149
$2,365
$2,334
$1,894
$1,284
$1,245
$1,207
$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 on the rise. 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 April 1 BR M/M % Change 2 BR April 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.