Apartments in Winter Park

31 - 60 of 79 Results
19
2496 Barbados Dr Unit 2496 Apartment for rent in Winter Park, FL
2496 Barbados Dr Unit 2496 Apartment for rent in Winter Park, FL
$2,000
Winter Park, FL
3 BR | Apr. 1, 2025
Contact
Dog Friendly
Storage
Dishwasher
33
1443 Harmon Ave Unit Room Apartment for rent in Winter Park, FL
1443 Harmon Ave Unit Room Apartment for rent in Winter Park, FL
$1,100
Winter Park, FL
3 BR | Available Now
Contact
Balcony/Deck/Patio
Dishwasher
Orwin Manor
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
Contact
House
1
3 Bed 2 Bath Townhouse In Winter Park! Apartment for rent in Winter Park, FL
$1,900
2611 Antilles Dr Winter Park, FL
3 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
Disability Access
Dishwasher
1
Spacious And Convenient 1 Bedroom. Won't Last! Apartment for rent in Winter Park, FL
$1,200
7341 Daniel Webster Dr #d Winter Park, FL
1 BR | Apr. 2, 2025
Contact
House
Storage
Pool
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
Contact
Dog Friendly
Air Conditioning
Storage
Dishwasher
11
Solis at Winter Park Apartment for rent in Winter Park, FL
$1,303 - 1,791
7502 Sun Key Blvd Winter Park, FL
1 - 2 BR | Available Now
Contact
Dog Friendly
Cat Friendly
Fitness Center
18
7637 Aloma Pines Ct Apartment for rent in Winter Park, FL
$2,395
Winter Park, FL
3 BR | Available Now
Contact
House
4
1523 Pickwood Ave Apartment for rent in Fern Park, FL
$1,795
Fern Park, FL
2 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
Dishwasher
1
3 Bedroom, 1.5 Bath Home At 469 Shoreview Ave., Winter Park 32789 Apartment for rent in Winter Park, FL
$2,200
469 Shoreview Ave Winter Park, FL
3 BR | Available Now
Contact
Dog Friendly
House
1
7490 Aloma Pines Ct Apartment for rent in Winter Park, FL
$2,375
Winter Park, FL
3 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
Storage
Dishwasher
1
Lakeside Manor On Lake Killarney Apartment for rent in Winter Park, FL
$1,450
2500 Lee Rd Winter Park, FL
2 BR | Available Now
Contact
Storage
Dishwasher
Pool
1
Spacious And Convenient 1 Bedroom. Won't Last! Apartment for rent in Winter Park, FL
$1,149
7429 Daniel Webster Dr #b-15c Winter Park, FL
1 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
Storage
1
Ncen130 Apartment for rent in Winter Park, FL
$1,750
130 N Center St Winter Park, FL
1 BR | Available Now
Contact
Dog Friendly
Cat Friendly
Air Conditioning
Dishwasher
Downtown Winter Park
11
303 Dryberry Way Apartment for rent in Fern Park, FL
$1,899
Fern Park, FL
2 BR | Available Now
Contact
House
17
1191 Sawmill Ct Apartment for rent in Winter Park, FL
$2,195
Winter Park, FL
3 BR | Apr. 5, 2025
Contact
House
1
Second Floor 2-bedroom, 2 Bathroom Condo Apartment for rent in Winter Park, FL
$1,575
7340 Swallow St Winter Park, FL
2 BR | Available Now
Contact
Dog Friendly
Cat Friendly
Dishwasher
93
3420 Hamlet Loop Apartment for rent in Winter Park, FL
$4,825
Winter Park, FL
3 BR | Ask for Availability
Contact
12
2848 Chantilly Ave Apartment for rent in Winter Park, FL
$2,650
Winter Park, FL
3 BR | Available Now
Contact
Dog Friendly
House
Storage
Dishwasher
$1,322 - 2,047
5 Autumn Breeze Way Winter Park, FL
1 - 3 BR | Available Now
Contact
Dog Friendly
Cat Friendly
Covered Parking
Fitness Center
Storage
$1,265 - 1,715
, FL
1 - 3 BR | Available Now
Contact
Dog Friendly
Cat Friendly
Air Conditioning
Balcony/Deck/Patio
Storage
1
$3,695
8151 Lazy Bear Ln Winter Park, FL
4 BR | Apr. 1, 2025
Contact
Dog Friendly
Cat Friendly
House
1
$2,120
1361 Ridgewood Ave Winter Park, FL
2 BR | Available Now
Contact
House
Dishwasher
1
$1,750
4622 N Goldenrod Rd Winter Park, FL
3 BR | Ask for Availability
Contact
Dishwasher
1
$3,295
Winter Park, FL
2 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
Dishwasher
Downtown Winter Park
1
$2,375
2710 Winter Park Rd Winter Park, FL
3 BR | Available Now
Contact
House
Audubon Park
1
$8,500
1731 Windsor Dr Winter Park, FL
4 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
Dishwasher
Pool
1
$3,400
1850 Whitehall Dr Winter Park, FL
3 BR | Available Now
Contact
Furnished
House
Pool
1
$2,200
2652 Galliano Cir Winter Park, FL
3 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
Dishwasher
1
$2,100
2032 Indiana Ave Winter Park, FL
2 BR | Available Now
Contact
Cat Friendly
House
Dishwasher
31 - 60 of 79 Results
  1. Home
  2. Orlando Area Apartments
  3. Winter Park

How much does it cost to rent an apartment in Winter Park?

Winter Park Apartments
Bed Type Average Rent Range
Studio $1,210 $880 - $1,340
1BR $1,400 $1,080 - $1,700
2BR $1,700 $1,400 - $2,000
3BR $2,150 $1,650 - $3,740
4+BR $3,150 $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.