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Apartments for Rent in Virginia Heights, Winter Park, FL

Average rent

$2,396
decreased by71%

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Great for

Social life
Wellness
Eco-living

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1221 Richmond Rd - Photo 1 of 1
New construction

5d+ ago

Virginia Heights house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1221 Richmond Rd, Winter Park, FL 32789

In-unit laundry | Garage parking | Swimming pool

5 beds

5 baths

$19,000

House for rent

1400 S Pennsylvania Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1400 S Pennsylvania Ave, Winter Park, FL 32789

In-unit laundry | Garage parking | Hardwood floor

4 beds

3 baths

$7,000

House for rent

Description

Property Status: Active A chic and trendy residence and winter park in an incredible location. A fully remodeled, one level four bedroom home with a fence corner lot. This home has an amazing curb appeal with its wide half circle, paved driveway, with plenty of parking flanked with lush mature landscaping. The open floor plan offers today's contemporary living and entertaining, with designer porcelain tile, trendy light fixtures, plantain shutters and a family room with high vaulted ceilings. The designer kitchen has just been totally remodeled with custom cabinets. Vikin

931 Cypress Ave - Photo 1 of 1

5d+ ago

Garden Acres house for rent in Winter Park

3 beds

1 bath

$1,995

$1,850

Price drop

House for rent

Description

COMING SOON! Newly remodeled 3/ 1 with carport, Bonus room/den/office and storage room. New kitchen cabinets and countertops with All new stainless steel appliances and remodeled bath. Located in the heart of winter park, within walking distance, to restaurants and shopping. Easy access to I-4. Do not miss out. Call for more inforlation All Flarent, Inc residents are enrolled in the Resident Benefits Package (RBP) for $50/month which includes liability insurance, credit building to help boost the resident’s credit score with timely rent payments, HVAC air filter del

1049 N Kentucky Ave - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

1049 N Kentucky Ave, Winter Park, FL 32789

In-unit laundry | Garage parking | Fitness center

3 beds

2 baths

$6,000

House for rent

Description

Property Status: Active Modern European-Inspired 3BR Home for Rent in the Heart of Winter Park. Live steps from everything that makes Winter Park extraordinary. This architect-designed attached home offers privacy, modern luxury, and unbeatable walkability — perfect for executives, creatives, fitness enthusiasts, and anyone seeking a refined long-term rental. 3 Bedrooms | 2.5 Bathrooms, Designed by Phil Kean, No HOA, enjoy the freedom of an attached home, Private two-story courtyard** and multiple outdoor living spaces, Walking distance to Park Avenue, Farmers Market, park

250 Carolina Ave - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

250 Carolina Ave, Winter Park, FL 32789

Garage parking | Swimming pool | Fireplace

2 beds

2 baths

$2,100

Condo for rent

Available Jan 13

Description

Welcome to Park West Condominiums, a highly desirable gated community in the heart of Winter Park, just steps from Park Avenue’s renowned shops, restaurants, cafés, galleries, and cultural attractions. This well-appointed 2-bedroom, 2-bath condominium offers an excellent blend of comfort, style, and location. Inside, the unit features a bright, open living area with vaulted ceilings, abundant natural light, and a wood-burning fireplace that adds warmth and character. The kitchen flows seamlessly into the living and dining spaces, making it ideal for everyday living and ent

1302 Michigan Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1302 Michigan Ave, Winter Park, FL 32789

In-unit laundry | Garage parking | Ceiling fan

3 beds

2 baths

$3,950

House for rent

Description

Property Status: Active Please visit our website at www ORLrent com you will find photos of our homes, tenant application, pet application, sample lease and more information. If applying for any of our homes all adult applicants over the age of 18 must submit a fully completed Application online. Application fee is $95.00 for each adult. An application reservation fee must be paid in the amount of one month's rent (in the form of a cashier's check or money order) to hold a property off the market. Office Phone: (407) 629-6330 Copyright © 2026 Stellar MLS. All rights reserv

Find rentals with popular amenities

New Construction

Swimming Pool

Dishwasher

Garage Parking

1315 Westchester Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1315 Westchester Ave, Winter Park, FL 32789

In-unit laundry | Garage parking | On-site laundry

2 beds

2 baths

$2,900

$2,800

Price drop

House for rent

Description

Property Status: Active Improved Price! Wow, expect to be impressed. This home has been lovingly updated and features handscraped wood floors and tile throughout...no carpeting! In addition, there is an expansive ceiling in the living room, updated kitchen with tumbled marble backsplash, sleek appliances, granite counters and lots of wood cabinetry for storage. This home has double pane windows, updated bathrooms with granite counters also! No detail has been left out. The primary bedroom is large enough for a king size bed, and a walk in closet. The kitchen, living

101 S Interlachen Ave #104 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condominium - WINTER PARK, FL

101 S Interlachen Ave #104, Winter Park, FL 32789

In-unit laundry | Assigned parking | Dishwasher

2 beds

2 baths

$3,800

Condo for rent

Description

Property Status: Active FOR RENT! SUPER RARE, GROUND FLOOR, DOWNTOWN WINTER PARK CONDO AT LACHEN HOUSE! This gorgeous 2 bedroom, 2 bath condo has been completely remodeled and features new laminate flooring, bright recessed lighting, and a stunning gourmet kitchen. Each bedroom is oversized with ample closet space. A charming courtyard off the back bedrooms provides a relaxing outdoor space to enjoy year round. Enjoy the convenience of one reserved covered parking space. Located just one block from Park Avenue, this condo is just a short stroll to all the amazing restauran

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1275 Michigan Ave #1275 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

3 BR, 3 BA in Winter Park

1275 Michigan Ave #1275, Winter Park, FL 32789

On-site laundry | Walk-in closets | High ceilings

3 beds

3 baths

$3,950

House for rent

Description

Welcome to this stunning townhome in the heart of Winter Park, built by award-winning Osprey Custom Home Builders. This residence combines timeless design, coastal aesthetic, certified greb construction, energy efficiency, and modern smart-home conveniences. Featuring 3 bedrooms, 2.5 baths, and an open-concept layout, the home is filled with designer finishes and thoughtful details throughout. The first floor offers inviting living and dining areas with plank-style tile floors, surround sound speakers, and high ceilings. The gourmet kitchen is equipped with maple cabinetry

1275 Michigan Ave - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

1275 Michigan Ave, Winter Park, FL 32789

In-unit laundry | Garage parking | On-site laundry

3 beds

2 baths

$3,950

House for rent

Description

Property Status: Active Welcome to this stunning townhome in the heart of Winter Park, built by award-winning Osprey Custom Home Builders. This residence combines timeless design, coastal aesthetic, certified greb construction, energy efficiency, and modern smart-home conveniences. Featuring 3 bedrooms, 2.5 baths, and an open-concept layout, the home is filled with designer finishes and thoughtful details throughout. The first floor offers inviting living and dining areas with plank-style tile floors, surround sound speakers, and high ceilings. The gourmet kitchen is equip

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104 Interlachen Avenue - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

2 BR, 2 BA in Winter Park

104 Interlachen Avenue, Winter Park, FL 32789

In-unit laundry | Ceiling fan | Outdoor space

2 beds

2 baths

$4,850

Condo for rent

Available Oct 1

Description

Welcome to the Cloisters, an exclusive lakefront condominium community in Winter Park, now available for lease. This first-floor two-bedroom, two-bath residence offers a thoughtfully updated open-concept layout and direct garden access. Entering from the main hallway, you enter into a welcoming interior where the kitchen sits to the right, featuring a breakfast bar that connects seamlessly to the dining and living areas. The open living space extends into a versatile sunroom, ideal as an office, library or den, with a ceiling fan and sliding doors leading out to the garden

690 Osceola Ave - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

2 BR, 2 BA in Winter Park

690 Osceola Ave, Winter Park, FL 32789

Hardwood floor

2 beds

2 baths

$3,400

Condo for rent

Available Nov 15

Description

Experience upscale living in this stunning 2-bedroom, 2-bath luxury condo featuring gorgeous raw wood floors in this breathtaking lakefront complex situated on the shores of the Winter Park Chain of Lakes and walking distance to Park Avenue, shopping, museums, restaurants and parks. The open-concept layout offers a seamless flow between the living, dining, and kitchen areas—perfect for both relaxing and entertaining. Enjoy resort-style amenities including a sparkling lakeside pool, a state-of-the-art fitness center, and an elegant clubhouse ideal for gatherings. With seren

1235 Ayrshire Street - Photo 1 of 1

5d+ ago

Orwin Manor house for rent in Orlando

1235 Ayrshire Street, Orlando, FL 32803

In-unit laundry | Garage parking | Hardwood floor

4 beds

2 baths

$3,500

House for rent

Available Oct 7

Description

This inviting single-story, 4-bedroom, 2-bath home is nestled in a peaceful suburban neighborhood that includes areas like Audubon Park and portions of downtown Orlando, which offer a unique blend of historic charm and modern living. The exterior showcases a fresh, light-colored façade complemented by a welcoming front yard, featuring lush greenery, vibrant flowers, and a well maintained lawn. A majestic oak tree draped in Spanish moss creates a picturesque frame, adding a touch of classic Southern elegance. Inside, warm wood floors flow throughout the home, enhancing its

1112 Chichester St - Photo 1 of 1

5d+ ago

Orwin Manor house for rent in Orlando

1112 Chichester St, Orlando, FL 32803

Deck | On-site management | Package service

4 beds

3 baths

$4,399

House for rent

Available Sep 22

Description

Discover this inviting four-bedroom, three-bathroom residence nestled in the highly sought-after Orwin Manor community of Orlando. Meticulously maintained, this home offers a thoughtful layout that seamlessly blends comfort and practicality. The main house features three spacious bedrooms and two full bathrooms, while a separate in-law suite or guest house includes an additional bedroom, bathroom, and full kitchenperfect for visitors or extended family. Situated on a rare 0.39-acre lotone of the largest in the neighborhoodthis property provides 2,252 square feet of welcomi

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These rentals are 10%-30% cheaper than the local average price for similar rentals.

Listings within 5 miles
1436 Minnesota Ave #1436 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

2 BR, 1 BA in Winter Park

1436 Minnesota Ave #1436, Winter Park, FL 32789

2 beds

1 bath

$1,299

Apartment for rent

Available Nov 12

Description

Updated 2 bedroom and 1 bath apartment located in the heart of the industrial district of Winter Park 32789. Close to Advent Health (Rollins campus), I-4 , Orange Avenue, 17-92, Rollins College, Fairbanks, Mills 50, College Park and Downtown Winter Park. Please no pets.

2663 Upper Park Rd - Photo 1 of 1

5d+ ago

Baldwin Park apartment for rent in Orlando

Garage Condo - ORLANDO, FL

2663 Upper Park Rd, Orlando, FL 32814

In-unit laundry | Garage parking | Swimming pool

1 bed

1 bath

$1,850

Apartment for rent

Description

Property Status: Active What a wonderful garage apartment that comes with ALL Utilities included! This one bedroom apartment is located off of Blue Jacket Park giving you access to everything that is wonderful about Baldwin Park. Inside you will find neutral wall color, wood flooring throughout, a number of windows providing lots of natural light. Windows have wood shutters. The kitchen is well appointed with stainless appliances and there is a full size stackable washer and dryer inside this home. In addition to the rent covering all utilities it also covers the HOA d

151 N Orlando Ave #203 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

151 N Orlando Ave #203, Winter Park, FL 32789

In-unit laundry | Furnished | On-site laundry

2 beds

1 bath

$2,200

Condo for rent

Description

Property Status: Active FURNISHED 6-12 month executive rental available immediately in Lake Killarney Condominiums. Perfect for one or two residents, this condo offers a bedroom with King-sized bed and walk-in closet, a separate office, and a sunroom with floor to ceiling windows. Newly installed bathroom and central air system. Combo washer/dryer unit in kitchen or optional coin laundry in building. Sorry, no tenant pets allowed per complex rules. One reserved parking space plus ample visitor parking. Residents will enjoy the private lakefront park, picnic tables and Adi

1550 Michigan Ave - Photo 1 of 1

5d+ ago

House for rent in Fairview Shores

1550 Michigan Ave, Fairview Shores, FL 32789

Air conditioning | On-site laundry | Assigned parking

1 bed

1 bath

$1,750

House for rent

Description

Welcome to your future home in the charming district of Winter Park, FL! This inviting property offers a warm atmosphere perfect for relaxation and convenience, surrounded by a vibrant community. This residence boasts spacious living equipped with essential comforts. With ample bedrooms and bathrooms, it accommodates various lifestyles. You'll appreciate the central heating and cooling systems, alongside the refreshing ceiling fans, ensuring your comfort year-round. Nestled in a prime location, you'll be just a short walk away from delightful restaurants and beautiful ou

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275 N Capen Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

275 N Capen Ave, Winter Park, FL 32789

In-unit laundry | Garage parking | Walk-in closets

4 beds

2 baths

$1,975

House for rent

Description

Property Status: Active This unique, old Florida style 4 ba / 2 ba 1180 sqft home features a single car garage, two baths, three smaller bedrooms and a master bedroom with walk in closet. Less than a mile away from desirable Park Avenue, and Rollins Collage. Washer/dryer included. Application Fee: $50 each adult (18+) **Full Credit/Skip/Eviction/Background check is done on all applicants. **Please have the following documents ready to attach as JPEG or PDF: - Drivers License - (3) Pay Stubs Office Phone: (407) 370-4400 Copyright © 2026 Stellar MLS. All rights reser

220 Overlook Rd #220 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

2 BR, 2 BA in Winter Park

220 Overlook Rd #220, Winter Park, FL 32789

In-unit laundry | Hardwood floor | Walk-in closets

2 beds

2 baths

$3,600

Apartment for rent

Available Sep 22

Description

Charming Cape Cod–style home available for lease in the heart of Winter Park. Ideally located just one block from Lake Mizell and moments from Park Avenue and Rollins College, this residence offers an exceptional lifestyle surrounded by premier shops, dining, and local amenities. The home features a spacious and inviting floor plan with a large living room, sunroom or dining area, and two generously sized bedroom suites. Interior highlights include beautiful hardwood floors, quartz countertops, walk-in closets, custom built-ins, and a private screened-in porch, perfect for

151 N Orlando Ave #226 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condominium - WINTER PARK, FL

151 N Orlando Ave #226, Winter Park, FL 32789

In-unit laundry | Furnished | Ceiling fan

2 beds

1 bath

$2,150

$1,750

Price drop

Condo for rent

Description

Property Status: Active Updated 2 bedrooms 1 bath conveniently located next to Winter Park Village and Trader Joes shopping center. Unit is can be furnished and is also for sale. Office Phone: (954) 545-5583 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

2979 Upper Park Road #2979 - Photo 1 of 1

5d+ ago

Baldwin Park townhouse for rent in Orlando

2 BR, 3 BA in Baldwin Park

2979 Upper Park Road #2979, Orlando, FL 32814

In-unit laundry | On-site laundry | Walk-in closets

2 beds

3 baths

$4,000

House for rent

Available Nov 17

Description

NOW LEASING | Move-in Ready December 1st! Experience upscale living in this beautifully appointed 1,897 SF townhome. This impressive home delivers both style and functionality in one of Orlando’s most desirable neighborhoods. Enter through the bright foyer into flowing living and dining areas. The well-appointed kitchen boasts warm wood cabinets, granite surfaces, ample pantry storage, and a breakfast bar for quick meals. An adjacent space serves as the perfect breakfast nook or casual seating area. The open family room extends your living space outdoors to a charming bric

300 Killarney Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

300 Killarney Dr, Winter Park, FL 32789

In-unit laundry | Garage parking | Fitness center

4 beds

3 baths

$8,500

House for rent

Description

Property Status: Active Exceptional Lakefront Living in the Heart of Winter Park Welcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location. This exquisite 4-bedroom, 3-bath home presents a rare opportunity to enjoy Winter Park's coveted lifestyle. Property Highlights: Situated on an oversized lot with coveted Lake Killarney frontage and a private boathouse, this elegant two-story home showcases engineered wood flooring throughout and an open-concept design flooded with natural light.

2979 Upper Park Rd - Photo 1 of 1

5d+ ago

Baldwin Park townhouse for rent in Orlando

Townhouse - ORLANDO, FL

2979 Upper Park Rd, Orlando, FL 32814

In-unit laundry | Garage parking | On-site laundry

2 beds

2 baths

$3,800

House for rent

Description

Property Status: Active New Year, New Home – Move In This Month! Start 2026 in style with this exceptional move-in ready townhome available immediately in sought-after Baldwin Park. With zero application fees for January move-ins, this is your opportunity to settle into upscale living without delay. This pet-friendly residence welcomes you and your furry companions. This beautifully appointed 1,897 square foot home perfectly balances elegance and everyday functionality. Enter through a bright foyer that opens to thoughtfully designed living spaces including separate livi

1565 Michigan Ave - Photo 1 of 1

5d+ ago

Apartment for rent in Fairview Shores

Half Duplex - WINTER PARK, FL

1565 Michigan Ave, Fairview Shores, FL 32789

In-unit laundry | Ceiling fan | Storage

2 beds

1 bath

$1,575

Apartment for rent

Description

Property Status: Active Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College. Office Phone: (407) 406-5300 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be indep

Showing 1 - 25 of 25 results
Home > Apartments in Winter Park > Virginia Heights Apartments For Rent
Updated: January 19, 2026

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Learn more about renting in Virginia Heights, Winter Park, FL

Virginia Heights, Winter Park apartment availability

Virginia Heights offers a limited selection of rental listings, with an average of about 2 rentals available each month. The majority of these listings are 1-bedroom apartments, followed by 2-bedroom and 3-bedroom options. Renters looking for a smaller, more intimate community may find Virginia Heights to be a good fit. With its limited but varied selection of rentals, Virginia Heights may appeal to those seeking a more low-key living environment.

Methodology: How we got this data

Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2024 rental inventory and prices.

Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.

Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.

Virginia Heights Apartments for rent FAQ

Can I afford an apartment for rent in Virginia Heights, FL?

To help you better understand how much rent you can afford, check out Zumper's rent calculator. Our rent calculator can help you learn more about Virginia Heights average rent prices.

What type of apartment rental is most common in Virginia Heights, Winter Park, FL?

4+ bedroom apartments are the most common type of rentals in Virginia Heights, Winter Park, FL right now.

What type of apartment rental is least common in Virginia Heights, Winter Park, FL?

4+ bedroom apartments are the least common type of rentals in Virginia Heights, Winter Park, FL right now.

Looking for apartments in Virginia Heights, Winter Park, FL near you?

🔑Available apartment rentals25
💰Best rent deal931 Cypress Ave
Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos