Apartments & Homes for Rent in Winter Park, FL

Apartment for rent at 2001 Glenridge Way, Winter Park, FL 32792

Discover luxury and comfort at The Fisher Apartments situated in highly sought-after Winter Park, Florida. The location is simply unbeatable, directly across from stunning Lake Baldwin and just a stone's throw from the vibrant shops, restaurants and other attractions along Park Avenue. Experience the finest in apartment living with our fully renovated homes. Our pet-friendly apartments feature the latest in smart home technology, new flooring and are freshly painted in neutral tones to suit your unique style. With in-apartment laundry, you'll enjoy unparalleled convenience and ease.

Condo for rent at 3035 George Mason Ave, Winter Park, FL 32792

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Managed by Real Property Management Sunstate - Orlando

$1,175

Condo1 Bed1 Bath656 ft²

3035 George Mason Ave

Winter Park, FL 32792

Water/Sewer Included. Second floor perch where price and location put you right where you want to be, with no noisy neighbors above you. Walking distance to grocery and commerce. Washer & Dryer included. Cool, easy-to-clean laminate flooring and ceiling fans. Community pool, playground. Perfect for first time renter. Plan to see this condo and get your application in today. We do not require last month's rent to be held. Security deposit is one to two months' rent.

House for rent at 2032 Indiana Ave, Winter Park, FL 32789

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Managed by Olde Town Brokers

$1,995

House2 Beds2 Baths1,100 ft²

2032 Indiana Ave

Winter Park, FL 32789

Newer 2/2 homes with a fully equipped kitchen with stainless steel appliances, large breakfast bar and recessed lighting, open floor plan, Light wood tile throughout, inside laundry with new washer and dryer. Primary bedroom with private bath, tub and shower. Hall bath with tub and shower. One car garage with an opener. Ceiling fans in both bedrooms and living area. 2 inch blinds in windows. Extra parking space for each unit and street parking. Small pets may be considered at owners discretion. These are tandem homes on the same lot. Refrigerator, Range, Dishwasher, Washer/dryer & Microwave/hood. Cats Allowed.

House for rent at 2816 Cady Way, Winter Park, FL 32792

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Managed by Innovative Realty

$2,395

House4 Beds2 Baths1,645 ft²

2816 Cady Way

Winter Park, FL 32792

Welcome to this spacious 4-bedroom, 2-bathroom home located in Winter Park, FL. This home features tile flooring in the living areas, new carpet and an open floorplan perfect for entertaining. The kitchen boasts extra countertop space and plenty of cabinet storage. The master bathroom includes a walk-in shower, while the two-car garage provides ample parking and storage space. Enjoy the convenience of washer/dryer hook-ups in the inside laundry room. Relax on the screened-in porch overlooking the backyard. With large closets throughout, this 1645 square foot home offers plenty of space for all your needs.

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Managed by PMI Property Alliance

$1,449

Townhouse2 Beds2.5 Baths1,031 ft²

3271 Forest Oaks Court #110

Winter Park, FL 32792

Welcome to this beautifully updated townhouse, ideally located in the sought-after Winter Park community. Featuring 2 spacious bedrooms and 2.5 bathrooms, this home offers the perfect blend of comfort and style for modern living. Enjoy the convenience of a community pool, providing a refreshing retreat on warm Florida days. The included washer and dryer make laundry day a breeze, adding ease to your daily routine. Step outside to your private patio, a serene space ideal for relaxing and enjoying the outdoors. This property is pet friendly.

Condo for rent at 2500 Lee Rd #142, Winter Park, FL 32789

Updated - 2 days ago

Managed by Real Property Management Verita

$1,650

Condo2 Beds1 Bath851 ft²

2500 Lee Rd #142

Winter Park, FL 32789

Discover this stunning gem nestled in the sought-after Lake Killarney community. This charming corner unit boasts privacy with no direct sunlight and has been fully renovated to perfection. Featuring 2 bedrooms and 1 bathroom, this condo offers over 850 sq. ft. of modern living space, highlighted by elegant vinyl flooring throughout. Residents can enjoy the serene community amenities, including a refreshing pool and a picturesque lakefront gazebo. Conveniently located just minutes from Park Avenue and I-4, this property combines comfort and accessibility in one of Winter Park's most desirable areas. Don't miss the chance to make this your new home.

Updated - 2 days ago

Managed by Shawn

$1,695

House2 Beds1 Bath800 ft²

1714 Miller Ave

Winter Park, FL 32789

Welcome to this charming duplex nestled in the heart of Winter Park. This 2-bedroom one bathroom with a one car carport 800sqft. has been totally remodeled with a well-designed floor plan. It includes all new appliances and washer and dryer hookups with tile floors throughout. Enjoy a bright and airy living space creating a welcoming atmosphere. Central heat and air. Nestled in a prime location you are mins from downtown Winter Park, downtown Orlando, Rollins College and Park avenue shopping. All RE/MAX 200 Realty Property Management Division residents are enrolled in the Resident Benefits Package (rbp) for $49.

Townhouse for rent at 105 Jergo Rd, Winter Park, FL 32792

Updated - 2 days ago

Managed by Orlando Property Management

$1,490

Townhouse3 Beds1.5 Baths

105 Jergo Rd

Winter Park, FL 32792

This unique 3 bedroom, 1.5 bathroom Duplex is ready to welcome it's new occupants. Spread over one story, this residence offers a perfect blend of space, comfort and modern amenities. Enjoy ample space for your family with generously sized living areas, including a wide living room for gatherings and quality family time. The Kitchen is equipped with all the essential appliances you would need. Retreat to generously sized bedrooms and indulge in ultimate relaxation in the upgraded bathrooms. Outside, a fenced backyard with a screened lanai offers the perfect setting for outdoor gatherings.

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Managed by 2cassa Management

$1,725

Condo2 Beds2 Baths1,018 ft²

2941 Antique Oaks Circle

Winter Park, FL 32792

Beautiful Winter Park 2/2 Condo on the first floor x Rent in front of Full Sail. Amenities include pool, sauna and clubhouse. Close to Park Ave, Advent Health Winter Park Hospital, Rollins College, Valencia College and University of Central Florida. Pool and Jacuzzy, Water, Sewer and Garbage & Range Refrigerator Dishwasher Microwave Washer Dryer. Dogs Allowed.

House for rent at 1716 Miller Ave, Winter Park, FL 32789

Updated - 2 days ago

Managed by Shawn

$1,695

House2 Beds1 Bath800 ft²

1716 Miller Ave

Winter Park, FL 32789

Updated - yesterday

Managed by Belmont Management Group

$1,625 - $1,950

Apartment1 Bed1 Bath667-800 ft²

520 N Orlando Ave

Winter Park, FL 32789

Discover urban living at it's best in Winter Park's The Lofts. Offering a unique 2-level loft, the allure of high ceilings, oversized windows and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People and much more. This unique urban charm sets The Lofts apart in Orlando.

Townhouse for rent at 3201 Royal St, Winter Park, FL 32792

New - this week

Managed by David Basher

$2,100

Townhouse3 Beds2 Baths1,292 ft²

3201 Royal St

Winter Park, FL 32792

Welcome to your future home in charming Winter Park. This delightful townhome combines comfort and convenience, offering the perfect space for cozy living and modern amenities. Step into a spacious, tiled living room featuring a stylish hardwood built-in cabinet that adds a warm and inviting touch. The upgraded kitchen is a culinary dream, boasting granite countertops, stainless steel appliances and ample cabinet space-perfect for preparing anything from quick snacks to gourmet meals. Adjacent to the kitchen, a bright and roomy dining area awaits, ideal for hosting family and friends.

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Managed by Innovative Realty

$2,795

Townhouse3 Beds2.5 Baths1,755 ft²

1355 Merrydale Way

Winter Park, FL 32792

1355 Merrydale Way is a beautiful 3 bedroom, 2.5 bath two story town home located in the Enclave at Hawks Crest gated community in Winter Park. Upon entry, you are welcomed into the oversized living area overlooking the kitchen and dining area. The kitchen features a full suite of stainless steel appliances including refrigerator, dishwasher, stove top and over the range microwave as well as spacious counter tops. Through the sliding glass doors in the living area is the large covered patio. The half bath is located with easy access for guests.

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Managed by Rick Protheroe

$1,700

Condo2 Beds1.5 Baths1,281 ft²

4880 Tangerine Ave

Winter Park, FL 32792

Clean Winter Park Condo for Rent in Wrenwood. 2-Story Condo with 2 Bedrooms, 1.5 Bathrooms, 1,281 sqft. (under air). Features include spacious living area downstairs, Carpeted upstairs bedrooms with walk-in closets, indoor laundry and private screened porch. Community offers quiet setting, Mature Landscaping & Community Pool. Location offers close access to Bus line, 417 & easy access to 436. Conveniently located just a short distance from downtown Winter Park. Water and sewer included. Schedule your showing today. Note: Some Photographs reflect a Virtual Staging. Community Pool. No dogs & No cats.

New - this week

Managed by Four Seasons

$1,500

Condo1 Bed1 Bath793 ft²

Four Seasons

200 Saint Andrews Blvd #407, Winter Park, FL 32792

Fantastic location with Winter Park address. This condo is one bedroom and one bathroom. Having a separate dining room in a one bedroom condo is unique. The living room leads out to a balcony through a sliding glass door with a storage closet and a view of the courtyard. The Four Seasons Community has it all. Pools, Jacuzzi, tennis court, playground, shuffleboard, a clubhouse and many courtyards and walking paths in a beautifully maintained landscaped surrounding. Centrally located to everything, restaurants, hospital and much more.

House for rent at 1833 Pineview Circle, Winter Park, FL 32792

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Managed by FirstKey Homes Management

$2,180

House3 Beds2 Baths1,380 ft²

1833 Pineview Circle

Winter Park, FL 32792

Please note that the advertised price may exclude additional fees. These include a mandatory $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; fees for amenities like smart home or internet service; and optional conditional fees for services like self-guided tours with third-party provider Rently ($1.99 to $11.99), pet fees/rent or pool maintenance, if applicable. HOA application and amenity fees, where applicable, are paid directly to the Hoa. Get rewarded for rental payments and more through FirstKey Homes Rewards - a rewarding and fun loyalty program.

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Managed by Progress Residential

$2,625

House4 Beds2 Baths1,756 ft²

5219 Ardmore Dr

Winter Park, FL 32792

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant. This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Attractive 3 bedroom, 2 bathroom home in Winter Park, FL. This home features: 1,756 square feet of generous space to move about, ceiling fans, an eat-in kitchen, a pantry for extra storage and a nice living room.

Condo for rent at 151 N Orlando Ave #142, Winter Park, FL 32789

Updated - this week

Managed by Atrium Property Management

$1,500

Condo1 Bed1 Bath582 ft²

151 N Orlando Ave #142

Winter Park, FL 32789

Welcome to your private retreat in the heart of Winter Park. This charming 1-bedroom, 1-bathroom condo in the highly desirable Lake Killarney Condominiums offers breathtaking views of Lake Killarney and unbeatable walkability to Trader Joe's, Winter Park Village, Park Avenue's renowned shops and restaurants, Rollins College and more. Enjoy the ultimate Florida lifestyle with access to a community pool, boat dock and ramp access-perfect for sunset strolls or weekend boating. Inside, you'll find wood-look vinyl plank flooring throughout, spacious closet, screened in patio. The unit also boasts two private entrances, offering added flexibility and privacy.

House for rent at 7429 Daniel Webster Dr, Winter Park, FL 32792

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Managed by Innovation Property Management

$1,125

House1 Bed1 Bath809 ft²

7429 Daniel Webster Dr

Winter Park, FL 32792

Welcome to this charming 1-bedroom, 1-bathroom house located in the desirable Winter Park, FL. This cozy home offers a comfortable living space with a range of amenities to enhance your lifestyle. The community pool is perfect for those warm Florida days, providing a refreshing retreat just steps away from your front door. Inside, you'll find beautiful ceramic tile flooring throughout, adding a touch of elegance to the space. The bathroom has been recently updated, ensuring a modern and fresh feel.

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Provided by Leasing Agent

$1,495

Condo2 Beds2 Baths1,045 ft²

1000 S Semoran Blvd #806

Winter Park, FL 32792

LB/O - Nice 2 bedroom 2 bathrooms, 2nd Floor Unit, Open Floor Concept, Living Area, Breakfast Area, Community Pool, Water Included. Application Credit upon Move In. Com And An Agent Will Respond Back With The Available Show Times. How To APPLY/ABOUT Our Application Process: Our application process has two phases. The first phase is to provide basic information so we may perform background screening upon payment of your application fee(s).

Viewing 1-20 of 82 rentals in Winter Park

What to Know About

Life in Winter Park & Beyond

Winter Park shares many of the great qualities that make Florida a desirable place to live.

Florida is a sunshine-filled state known for its beautiful beaches, warm weather, and world-famous theme parks like Walt Disney World, Universal Studios, and Sea World. From its iconic beaches to vibrant cities, you have a unique blend of outdoor adventure and urban excitement. Explore the state's past by visiting attractions like the Kennedy Space Center, the Museum of Florida History, or the Perez Art Museum Miami. In addition, Florida is home to renowned universities such as the University of Florida and Florida State University, University of Miami.

With hundreds of miles of sandy beaches, crystal-clear springs, and lush everglades, Florida is a paradise for visitors and residents alike. The state is also home to several professional sports teams, including the Miami Dolphins (NFL), Tampa Bay Buccaneers (NFL), Florida Panthers (NHL), Tampa Lighting (NHL), Miami Marlins (MLB), Orlando Magic (NBA), and Miami Heat (NBA). Experience all that Florida has to offer, from its stunning beaches and vibrant atmosphere to its rich traditions and thriving economy.

Discover the magic of living in Florida, where the sun shines bright, the economy thrives, and the quality of life is unparalleled, making it the perfect place to call home.

Rental Market Trends

Winter Park, FL

As of May 2025, Winter Park's rental market is competitive, with strong renter demand causing quick leasing times for well-priced units. Winter Park's average rent is 20.2% ($436) lower than the Florida average of $2,161 and 3.8% ($68) lower than the U.S. average of $1,793.

Average Rent

$1,725

Monthly ChangeMonth Over Month Change

4.9% ($89)

Yearly ChangeYear Over Year Change

11.3% ($220)

Avg. Days on MarketAverage Days on Market

Unit Type	Average Rent	Monthly ChangeMonth Over Month Change	Yearly ChangeYear Over Year Change
1 Bed	$1,546	11.6% ($161)	2.7% ($43)
2 Beds	$1,884	16% ($260)	2.8% ($51)
3 Beds	$2,290	0.4% ($8)	3.7% ($82)

Nearby Cities	Average Rent	Avg. Rent vs. Winter ParkAverage Rent vs. Winter Park	Avg. Days on MarketAverage Days on Market
Maitland	$1,823	5.7% ($98)	30 days
Casselberry	$2,045	18.6% ($320)	24 days
Altamonte Springs	$1,476	14.4% ($249)	24 days
Winter Springs	$2,140	24.1% ($415)	22 days
Orlando	$2,089	21.1% ($364)	31 days

Rental market trends are calculated using listing data from RentalSource.

Frequently Asked Questions

Winter Park Rental Market FAQs

Explore rental prices, market trends, and availability in Winter Park, FL.

What is the average rent in Winter Park, FL?

The average rent in Winter Park, FL is $1,725 per month.

What is the rental price range for homes in Winter Park, FL?

Homes in Winter Park typically rent for between $1,082 and $2,977 per month, with an average of $1,725 per month.

What is the average rent for different bedroom sizes in Winter Park, FL?

In Winter Park, the average rent for a 1-bedroom home is $1,546 per month, for a 2-bedroom home, $1,884 per month, and a 3-bedroom home is $2,290 per month.

How do rent prices in Winter Park, FL compare with the national average?

The average rent in Winter Park is 3.8% ($68) lower than the national average of $1,793 per month.

How have rent prices in Winter Park, FL changed recently?

The average rent in Winter Park has decreased by 4.9% ($89) in the last month and decreased by 11.3% ($220) over the past year.

How competitive is the rental market in Winter Park, FL?

The rental market in Winter Park, FL, is currently competitive, with strong renter demand causing quick leasing times for well-priced units.

How long do rentals stay on the market in Winter Park, FL?

In Winter Park, FL, the average rental stays on the market for approximately 31 days. While most properties are rented within this timeframe, factors like seasonality, demand, and property type can affect how quickly a rental leases.

How many rental properties are available in Winter Park, FL?

There are currently 82 rental properties available in Winter Park, FL.

Can I afford to rent a home in Winter Park, FL?

Based on the current averages, a household would need an annual income of $75,360 to comfortably afford a 2-bedroom home in Winter Park.

Apartments & Homes for Rent in Winter Park, FL

Life in Winter Park & Beyond

Winter Park, FL

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