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Apartments for Rent in Winter Park, FL

1-20 of 31 rentals

2+ Beds

Condo for rent at 3007 George Mason Ave #H, Winter Park, FL 32792

Updated - 2 days ago

Managed by Allegiant Management Group

$1,649

Condo2 Beds2.5 Baths1,090 ft²

3007 George Mason Ave #H

Winter Park, FL 32792

Move-in ready and beautifully updated, this two-story condo in the desirable Colonies Community offers 2 bedrooms and 2.5 bathrooms, with each bedroom featuring it's own private en-suite bath. All bedrooms are located upstairs. While a convenient half bath is located on the first floor. The home features fresh interior paint, new flooring in many rooms and numerous upgrades throughout. The kitchen comes fully equipped with a range, refrigerator, dishwasher and microwave. Living and dining areas provide a welcoming space perfect for relaxing or entertaining. A private balcony extends off one of the bedrooms, offering a quiet outdoor retreat.

Updated - yesterday

Managed by The Fisher Apartments

$1,849 - $1,999

Apartment2 Beds1 Bath838 ft²

2001 Glenridge Way

Winter Park, FL 32792

Welcome to The Fisher - Winter Park's hidden gem. Discover modern, pet-friendly living just steps from Lake Baldwin Trail. Located directly across the street from the scenic loop and within walking distance to downtown Baldwin Park, The Fisher offers unbeatable value in one of Central Florida's most sought-after neighborhoods. Choose from beautifully updated one and two bedroom apartments featuring high-speed Wi-Fi, premium appliances, in-home laundry, spacious layouts and smart-home technology. Outside your door, enjoy top-tier amenities including a refreshing community pool, gated dog park, outdoor kitchen and a cozy firepit.

Updated - today

Managed by Orlando Communities

$1,899

Apartment2 Beds2.5 Baths1,175 ft²

3656 N Goldenrod Rd

Winter Park, FL 32792

Welcome to Tuscany Villas, located in the charming Winter Park, FL. Our community offers a serene and inviting atmosphere, perfect for those seeking a peaceful retreat. Tuscany Villas is nestled in the heart of Orange County, providing residents with convenient access to all the attractions and amenities this vibrant area has to offer. At Tuscany Villas, we understand the importance of relaxation and recreation, which is why we offer an 8 Days community pool. Take a refreshing dip in the crystal-clear waters or lounge poolside while soaking up the warm Florida sun.

Updated - this week

Managed by Douglas E Homes

$1,499

Apartment2 Beds2 Baths1,049 ft²

1000 S Semoran Blvd #816

Winter Park, FL 32792

Charming 2-Bedroom, 2-Bathroom Condo in Winter Park - Move-In Ready. This lovely second-floor unit in Golfside Villas features brand-new carpet installed in 2025. Step into a spacious, open-concept kitchen and living area, offering a comfortable and inviting space to relax and entertain. The master bedroom includes an en-suite bathroom, while the generously sized second bedroom also boasts new carpet. A conveniently located hallway bathroom provides easy access for both guests and residents. While the property does not have washer and dryer connections, the community offers a laundry facility for residents' convenience. Rent includes water and sewer services.

Apartment for rent at 1500 Gay Rd #3B, Winter Park, FL 32789

Featured

Managed by Specialized Property Management Orlando

$2,199

Apartment2 Beds2 Baths1,100 ft²

1500 Gay Rd #3B

Winter Park, FL 32789

Lakefront Living at It's Best: Renovated 1st Floor End Unit on Lake Killarney. Experience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney. Key Features: Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings. Water Activities: Benefit from the community boat ramp and access to a skiable lake for endless water fun. Prime Location: Just a short walk to shopping centers, theaters and restaurants and minutes from Park Avenue with easy access to I-4.

Managed by Alexan Wp2

$2,110 - $2,435

Apartment2 Beds2 Baths

Alexan Wp2

741 Clay St, Winter Park, FL 32789

Alexan WP2 is an apartment community designed with you in mind, putting extra care into every detail. Details that make your living space an extension of you, with open floor plans and extra touches like keyless entry and Usb outlets. Our social spaces, like the clubhouse and courtyard with pool, help you make the most of socializing or downtime. Located just east of I-4, you'll find yourself in the middle of the charm and history of Winter Park, but also connected to the energy of Orlando.

Apartment for rent at 3651 N Goldenrod Rd, Winter Park, FL 32792

Updated - this week

Managed by C F R P Realty

$1,595

Apartment2 Beds2 Baths840 ft²

3651 N Goldenrod Rd

Winter Park, FL 32792

Wow, this location is fantastic for the 2 bedroom, 2 bath, updated condo. This community of Lancelot at Winter Park, which is off of N. Goldenrod, has easy access to University Blvd. From University Blvd you can go into Seminole County or further into Orange County very easily. Your commute to downtown Orlando, UCF, Valencia, Full Sail, Rollins College is only a few minutes. Easy Access to The 417/408. The condo is a 1st floor unit that has good space. From the moment you enter the living room/dining room combination, the space feels very cozy and at home.

Condo for rent at 2500 Lee Rd #105, Winter Park, FL 32789

Featured

Managed by Specialized Property Management Orlando

$1,799

Condo2 Beds2 Baths996 ft²

2500 Lee Rd #105

Winter Park, FL 32789

This condo has frontage on and access to Lake Killarney. It is a spacious 2bed/2bath with a beautiful kitchen with plenty of cabinet space and stainless steel appliances. Condo also has fresh paint, new flooring and bathrooms have been updated as well. The community has a pool and boat ramp. Very quiet neighborhood, a great place to live and a great location. Close to I-4, local shopping and dining. Water included in rent. Additional HOA approval required. This property is eligible for deposit alternative coverage in lieu of a security deposit.

Featured

Managed by Belmont Management Group

$2,900

Condo3 Beds2 Baths1,130 ft²

644 N Knowles Ave #8

Winter Park, FL 32789

Welcome to your private retreat in the heart of Downtown Winter Park. This exclusive address affords views of the world famous Winter Park 9 course and the timeless Casa Feliz, right from your balcony. This wonderful 3/2 Large condo features: a Fully renovated kitchen, equipped with designer touches and top of the line stainless steel appliances, solid surface flooring throughout, clean and updated bathrooms and much more. The spectacular location provides it's future resident with the ability to walk to Rollins College, Park Avenue and all of it's restaurants, cafes and shops. Rollins community and Staff are welcome.

Condo for rent at 1917 Woodcrest Dr #C, Winter Park, FL 32792

Updated - 3 days ago

Managed by Atrium Property Management

$1,895

Condo2 Beds2 Baths987 ft²

1917 Woodcrest Dr #C

Winter Park, FL 32792

Welcome to this charming 2-bedroom, 2-bathroom home located at the Oaks Condominium community. Centrally located between the heart of Downtown Orlando and the finest shopping and dining of in desirable Winter Park. This rental includes water service along with monthly pest control by the Hoa. This cozy unit offers a comfortable living space with updated kitchen and custom features you have to see to really appreciate. With spacious bedrooms and great floorplan privacy is a key factor. An added bonus is that you can enjoy a community pool, perfect for those warm Florida days.

Featured

Managed by C F R P Realty

$1,500

Apartment2 Beds2 Baths840 ft²

3651 N Goldenrod Rd

Winter Park, FL 32792

Beautiful ground floor unit with all tile flooring. This 2 bed/2 bath has an open floor plan. The kitchen is open to the living room and dining area and features all appliances, granite counter, a breakfast bar and sliding glass doors to the patio, Both bedrooms are good size. Both bathrooms have been updated. Inside utility with a Stackable Washer and Dryer. Tenants are Required to have renters insurance with 100k of liability insurance or landlord's liability policy. No Pets Allowed. Convenient location for shopping, dining, Full Sail University, UCF and all major roads.

New - this week

Managed by Belmont Management Group

$2,800

Apartment3 Beds2 Baths2,319 ft²

5334 Lake Howell Rd

Winter Park, FL 32792

Rollins Students Welcomed. Highlights: Fully Renovated - Spacious Floor Plan - Tile Throughout - Minutes From Winter Park Shops + Restaurants - Spacious Front Yard. Move-in ready starting on July 20th. Schedule your tour today. Looking for a charming home in the beautiful Winter Park area? Look no further than this fully renovated 3 bed, 2 bath home. The bright and open-concept living area features beautiful tile throughout, making the space both modern and welcoming. The spacious living room is perfect for entertaining guests, while the large front and backyards offer plenty of room for outdoor activities.

Updated - today

Managed by HomeRiver Group Florida

$1,450

Condo2 Beds2 Baths1,042 ft²

3054 George Mason Ave #C6

Winter Park, FL 32792

Estimated Total Monthly Leasing Price: $1,499.95. Base Rent: $1,450. Filter Delivery: $5. Renters Insurance: $10.95. $1M Identify Protection, Credit Building, Resident Rewards, Move-In Concierge: $34. The estimated total monthly leasing price does not include utilities or optional/conditional fees, such as: pet, utility service and security deposit waiver fees. Our Resident Benefits Package includes required Renters Insurance, Utility Service Set-Up, Identity Theft Protection, Resident Rewards, HVAC air filter delivery (where applicable) and Credit Building, all at the additional monthly cost shown above. Welcome. A charming 2-bedroom, 2-bathroom condo located in the well-established Colonies community of Winter Park awaits.

New - this week

Managed by Lissany Kelly

$1,795

Apartment2 Beds1.5 Baths900 ft²

2667 Rook Cove

Winter Park, FL 32792

Newly Remodeled Home in the Heart of Winter Park. 2667 Rook Cove, Winter Park, FL. Welcome to this stunning 2-bedroom, 1.5-bathroom home, nestled in a quiet cul-de-sac in the highly sought-after Winter Park area. Just remodeled, this unit features a brand-new kitchen with modern shaker-style cabinets, sparkling white granite countertops and all-new stainless steel appliances - the perfect blend of style and function. Enjoy the comfort of new light fixtures and ceiling fans throughout, as well as convenient amenities like a microwave, washer, dryer and a fenced yard - great for relaxing outdoors or giving your pets space to roam.

Updated - this week

Managed by Anderson Commercial & Asset Management

$1,800

Apartment2 Beds1 Bath826 ft²

2045 S Lakemont Ave

Winter Park, FL 32792

Welcome to Maccallum Sub A/98, presented by Anderson Commercial & Asset Management. We have several units available for lease. For more information and to schedule a showing, please contact us. Fridge, Stove, Dishwasher, washer Dryer, Microwave & water sewer & Trash.

Featured

Managed by Central Florida Property Management

$1,450

Condo2 Beds2 Baths840 ft²

3651 N Goldenrod Rd #B109

Winter Park, FL 32792

This home is ready for move in July 1st. You will love this fabulous condo in the charming and great central location of Winter Park /East Orlando. The 2 bedroom, 2 bath condo offers a spacious living and dining combo, with an open floor plan, large kitchen with lots of cabinet and storage space. There are Sizable closet space in both bedrooms. The unit comes with many upgrades and beautiful tile throughout the entire unit. Ample parking and inside laundry hookups. Convenient to highways, shopping, restaurants, minutes away from university of Central Fl(ucf), Valencia College and Full Sail University.

Condo for rent at 1250 S Denning Dr #204, Winter Park, FL 32789

Featured

Managed by Atrium Property Management

$1,865

Condo2 Beds2 Baths908 ft²

1250 S Denning Dr #204

Winter Park, FL 32789

Convenient, Connected, & Full of Character. Discover the perfect blend of nature, culture and comfort in this beautifully maintained 2-bedroom, 2-bathroom condo located in the highly desirable Mead Gardens Condominiums in Winter Park. Just minutes north of Downtown Orlando, this community is in the perfect setting and features a sparkling community pool, on site laundry facilities and courtyard outdoor spaces. Step inside and feel instantly at home in this warm and welcoming 2-bedroom condo, featuring rich wood flooring throughout and the convenience of an in-unit washer and dryer, located on the second floor.

Condo for rent at 7726 Country Place, Winter Park, FL 32792

Managed by Orlando Cribs

$1,900

Condo2 Beds2 Baths1,068 ft²

7726 Country Place

Winter Park, FL 32792

1st Floor Condo In Winter park Florida.

Apartment for rent at 1500 Gay Rd #26-B, Winter Park, FL 32789

New - this week

Managed by Central Florida Property Management

$1,949

Apartment2 Beds2 Baths1,026 ft²

1500 Gay Rd #26-B

Winter Park, FL 32789

Stop your search. This beautifully remodeled first-floor poolside unit is located in a desirable Lakefront Community on skiable Lake Killarney. The home features an updated, oversized kitchen with quartz countertops, stainless steel appliances and custom wood cabinetry. Enjoy stylish wood plank tile floors throughout and fresh paint that enhances the home's modern feel. The spacious kitchen and great room flow seamlessly, offering a perfect space for entertaining, with views of the pool just outside. Relax by the lake and watch stunning sunsets or take a dip in the heated community pool year-round.

Apartment for rent at 115 Scottsdale Square, Winter Park, FL 32792

Featured

Managed by Winter Park Woods Condos

$1,595

Apartment2 Beds2 Baths1,020 ft²

115 Scottsdale Square

Winter Park, FL 32792

Special offer. 2 Months Free rent for Immediate Move-in. While supplies last, limited time offer. This community boasts a prime location that effortlessly combines charm with convenience. Nestled in a well established neighborhood, it offers residents easy access to an array of amenities, including local shops, cafes and restaurants, all just a short stroll away. The mature landscaping creates a tranquil atmosphere, inviting residents to take leisurely walks and enjoy the scenery. Characterized by it's unique architectural styles the community features a variety of homes that reflect the history and character of Winter Park.

Viewing 1-20 of 31 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 August 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 12.2% ($252) lower than the Florida average of $2,067 and 1.4% ($25) higher than the U.S. average of $1,790.

Average Rent

$1,815

Monthly ChangeMonth Over Month Change

1.7% ($31)

Yearly ChangeYear Over Year Change

11.1% ($226)

Avg. Days on MarketAverage Days on Market

Unit Type	Average Rent	Monthly ChangeMonth Over Month Change	Yearly ChangeYear Over Year Change
1 Bed	$1,692	0.9% ($16)	12.6% ($189)
2 Beds	$1,868	10.2% ($213)	7.7% ($134)
3 Beds	$2,665	2.7% ($75)	27.6% ($576)

Nearby Cities	Average Rent	Avg. Rent vs. Winter ParkAverage Rent vs. Winter Park	Avg. Days on MarketAverage Days on Market
Maitland	$2,222	22.4% ($407)	30 days
Casselberry	$1,689	6.9% ($126)	24 days
Altamonte Springs	$1,599	11.9% ($216)	24 days
Winter Springs	$2,088	15% ($273)	22 days
Orlando	$1,918	5.7% ($103)	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 $1,815 per month.

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

Apartments in Winter Park typically rent for between $1,184 and $3,465 per month, with an average of $1,815 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 apartment is $1,692 per month, for a 2-bedroom apartment, $1,868 per month, and a 3-bedroom apartment is $2,665 per month.

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

The average rent in Winter Park is 1.4% ($25) higher than the national average of $1,790 per month.

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

The average rent in Winter Park has increased by 1.7% ($31) in the last month and decreased by 11.1% ($226) 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 80 rental properties available in Winter Park, FL.

Can I afford to rent an apartment in Winter Park, FL?

Based on the current averages, a household would need an annual income of $74,720 to comfortably afford a 2-bedroom apartment in Winter Park.