Apartments in Winter Park

31 - 60 of 70 Results
11
$1,231 - 1,365
7502 Sun Key Blvd Winter Park, FL
1 - 2 BR | Available Now
Contact
Dog Friendly
Cat Friendly
Fitness Center
1
$1,597
7328 Forest Hill Ct Winter Park, FL
2 BR | Available Now
Contact
House
29
$3,250
Winter Park, FL
4 BR | Dec. 18, 2026
Contact
Dog Friendly
Cat Friendly
House
10
$1,395
Winter Park, FL
1 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
33
$1,300
Winter Park, FL
3 BR | Available Now
Contact
Balcony/Deck/Patio
Dishwasher
Orwin Manor
25
$1,975
Winter Park, FL
2 BR | Available Now
Contact
33
$1,590
Winter Park, FL
2 BR | Ask for Availability
Contact
39
$2,880
Winter Park, FL
3 BR | Available Now
Contact
19
$1,362 - 2,227
3440 N Goldenrod Rd Winter Park, FL
1 - 3 BR | Available Now
Contact
Dog Friendly
Cat Friendly
Fitness Center
Dishwasher
1
$1,895
7101 Swallow St Winter Park, FL
3 BR | Ask for Availability
Contact
House
Storage
Dishwasher
11
$1,750
Winter Park, FL
3 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
Air Conditioning
Dishwasher
67
$1,499
Winter Park, FL
2 BR | Ask for Availability
Contact
31
$1,895
Fern Park, FL
2 BR | Available Now
Contact
Dog Friendly
House
36
$4,950
Winter Park, FL
4 BR | Available Now
Contact
8
$1,688
Winter Park, FL
1 BR | Ask for Availability
Contact
50
$1,895
Winter Park, FL
3 BR | Ask for Availability
Contact
15
$2,250
Winter Park, FL
3 BR | Available Now
Contact
House
Air Conditioning
Dishwasher
1
$2,495
1966 Staunton Ave Winter Park, FL
3 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
Dishwasher
1
$2,540
408 London Rd Winter Park, FL
3 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
Dishwasher
1
$1,800
Winter Park, FL
2 BR | Available Now
Contact
Dishwasher
1
$1,495
3000 3098 Oaks Cir Winter Park, FL
2 BR | Available Now
Contact
1
$1,195 - 1,470
600 N Semoran Blvd Winter Park, FL
1 - 2 BR | Available Now
Contact
1
$1,325
3651 N Goldenrod Rd Unit F205 Winter Park, FL
2 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
1
$2,100
301 S Capen Ave Winter Park, FL
3 BR | Available Now
Contact
Dog Friendly
Cat Friendly
House
Dishwasher
Downtown Winter Park
0
1
$8,500
660 Osceola Ave Winter Park, FL
3 BR | Available Now
Contact
Dishwasher
1
$1,995
700 Melrose Ave Unit A-5 Winter Park, FL
2 BR | Available Now
Contact
House
1
$2,240
1666 Tremont Ln Winter Park, FL
3 BR | Available Now
Contact
House
Dishwasher
1
$3,400
2217 Sussex Rd Winter Park, FL
4 BR | Ask for Availability
Contact
Dog Friendly
House
Dishwasher
Pool
20
$880 - 1,480
2400 Howell Branch Road Winter Park, FL
Studio - 3 BR | Ask for Availability
Contact
Dog Friendly
Cat Friendly
Air Conditioning
Surface Parking
Balcony/Deck/Patio
31 - 60 of 70 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 $1,040 $880 - $1,970
1BR $1,280 $1,070 - $2,060
2BR $1,520 $1,300 - $1,950
3BR $1,950 $1,500 - $4,510
4+BR $3,400 $3,250 - $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

Campuses Nearby

Winter Park:
November Rent Report

Welcome to the November 2026 Winter Park Apartment Report. In this assessment of the local rental market, Rentable data scientists and rental experts break down the November 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

$50
$40
$30
$10
$0
Dec. 2025
Jan. 2026
Feb. 2026
Mar. 2026
Apr. 2026
May. 2026
Jun. 2026
Jul. 2026
Aug. 2026
Sep. 2026
Oct. 2026
Nov. 2026
1 BR       2 BR

Winter Park Rent Prices Decrease From October to November

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

November 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.

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