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Apartments for Rent in Winter Park, FL

291 rentals

2460 Firstlight Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

3 BR / 2.5 BA Townhouse In Hawks Crest

2460 Firstlight Way, Winter Park, FL 32792

In-unit laundry | Walk-in closets | Carpet

3 beds

2 baths

$2,675

House for rent

Gated Townhouse with Stylish Upgrades & Community Perks

This modern 3-bedroom, 2.5-bathroom townhouse spans 1,755 sqft in the gated Hawks Crest community. It features an open floor plan, a chic kitchen with granite counters and stainless steel appliances, plus a serene backyard patio. The upstairs primary suite boasts dual sinks and a walk-in closet. Enjoy community amenities like a pool, playground, and park. Conveniently located near Lake Howell, shopping, and dining, this pet-friendly residence is perfect for a vibrant lifestyle.

7761 Country Pl - Photo 1 of 1

5d+ ago

House for rent in Winter Park

House for rent

Charming Home with Screened Patio & Modern Finishes

This lovely 3-bedroom, 2-bathroom home features tile flooring throughout, eliminating carpet worries. The kitchen boasts stainless steel appliances and granite countertops. The spacious master bedroom includes a walk-in closet, while both bathrooms feature granite countertops. Enjoy the outdoors on the screened patio and relax in the fenced backyard. Conveniently located near dining, shopping, and entertainment options, this pet-friendly residence is ready for new tenants!

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

$7,900

House for rent

Elegant Lakefront Retreat with Gourmet Kitchen

A stunning 4-bedroom, 3-bath lakefront residence boasts 2,476 sq ft of sophisticated living in Winter Park. Featuring engineered wood flooring, soaring ceilings, and an open-concept design, this home is filled with natural light. The gourmet kitchen with stainless appliances and a generous island is perfect for entertaining. Enjoy a private courtyard with a hot tub, plus a detached bonus room ideal for a home office or fitness studio. Walk to dining, shopping, and cultural attractions nearby.

2500 Lee Rd #244 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condominium - WINTER PARK, FL

2500 Lee Rd #244, Winter Park, FL 32789

In-unit laundry | Assigned parking | Swimming pool

1 bed

1 bath

$1,465

Condo for rent

Bright & Spacious Condo with Pool Access

Enjoy easy living in this charming 1-bedroom, 1-bathroom condo featuring 645 sq. ft. of bright space with an open layout and plenty of storage. The well-equipped kitchen includes a dishwasher, and the community offers a swimming pool and assigned parking. Located near Park Avenue and Rollins College, this home is perfectly situated for those seeking comfort and convenience in Winter Park.

147 S Interlachen Ave #250 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

Coming soon Walk to Park Ave. 3 Bedroom 5 Bathroom 3320 s.f. -Single level condo.

147 S Interlachen Ave #250, Winter Park, FL 32789

In-unit laundry | Air conditioning | Garage parking

3 beds

5 baths

$9,500

Apartment for rent

Available Feb 1

Luxurious 3-Bedroom Oasis with Poolside Charm

Experience luxury living in this 3-bedroom, 5-bathroom apartment featuring 3,320 sq. ft. of sun-filled space with private elevator access. Enjoy two serene balconies overlooking a beautiful pool and spa area. The sophisticated interior boasts a fireplace and a spacious master suite with dual closets and exquisite bath. Conveniently located steps from Park Avenue and Central Park, this residence also offers secure parking and ample storage, perfect for a vibrant Winter Park lifestyle.

1695 Lee Rd #E107 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

1695 Lee Rd #E107, Winter Park, FL 32789

In-unit laundry | Air conditioning | Balcony

1 bed

1 bath

$1,300

Apartment for rent

Available Feb 1

Charming Downstairs Apartment with Pool Access

This delightful 1-bedroom, 1-bathroom apartment features modern updates throughout, including an updated kitchen and bathroom. Enjoy the convenience of in-unit laundry, central air, and a private patio. Community amenities include a refreshing pool and assigned parking. Cable and internet are included in the rent, making this 725 sq. ft. space both cozy and convenient for comfortable living. Perfect for those seeking a vibrant lifestyle in Winter Park!

3050 Autumn Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

3/2 In Desirable Winter Park Neighborhood

3050 Autumn Ct, Winter Park, FL 32792

In-unit laundry | Swimming pool | Dishwasher

3 beds

2 baths

$2,000

House for rent

Available Feb 1

Family-Friendly Townhome with Community Pool Access

This charming 3-bedroom, 2-bathroom townhome in a sought-after A-rated school district features a spacious corner lot and a welcoming porched back patio. Enjoy easy living with an included washer and dryer, modern appliances, and a well-maintained community pool for relaxation and recreation. Perfect for families seeking comfort and convenience in a vibrant community, this home offers a delightful blend of space and amenities. Experience the best of family living!

2942 Antique Oaks Cir #82 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Parkview Condominiums

2942 Antique Oaks Cir #82, Winter Park, FL 32792

In-unit laundry | Swimming pool | Dishwasher

1 bed

1 bath

$1,380

Condo for rent

Available Mar 1

Cozy 1-Bed Condo Near Full Sail University

This charming second-floor 1-bedroom condo features 749 sq. ft. of laminate flooring and a modern kitchen with essential appliances. Enjoy the convenience of in-unit laundry, plus the added benefit of water and sewer included in rent. Residents can relax by the community pool or unwind in the hot tub, all in a pet-friendly environment close to Full Sail University. Perfect for students or young professionals!

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1860 Via Contessa #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Newly Renovated - 8 Bedroom 6 Bathroom House In Winter Park

1860 Via Contessa #NA, Winter Park, FL 32789

In-unit laundry | Air conditioning | Garage parking

8 beds

6 baths

$15,550

House for rent

Available Jan 27

Expansive Family Haven with In-Law Suite & Pool

This stunning 7,000 SF home features 8 bedrooms and 6 baths across three levels, perfect for family living. Enjoy a chef-inspired kitchen with quartz countertops, cozy living spaces with a gas fireplace, and dual primary suites. An impressive lower level boasts an in-law suite, gym, and game room. The outdoor area includes a covered patio and pool deck, ideal for entertaining. Located in a quiet cul-de-sac near Park Avenue, this residence is a perfect blend of luxury and comfort.

438 W Swoope Ave - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

438 W Swoope Ave, Winter Park, FL 32789

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

4 beds

3 baths

$4,795

$4,495

Price drop

House for rent

Available Dec 17

Modern Townhome with Spacious Living & Elegant Design

Experience luxurious living in this modern 4-bedroom, 3.5-bath townhome featuring high-end finishes and an open-concept layout. The chef's kitchen boasts quartz countertops and stainless appliances, while large windows fill the spacious primary suites with light. Versatile third-floor spaces, ample storage, and a rear-entry garage enhance convenience. Located just steps from Winter Park's vibrant attractions, this elegant residence offers a perfect blend of comfort and style.

2992 Chantilly Ave #2992 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

3 BR, 2 BA in Winter Park

2992 Chantilly Ave #2992, Winter Park, FL 32789

Outdoor space

3 beds

2 baths

$2,880

Apartment for rent

Available Jan 21

Charming Pool Home with Bonus Room & Sunroom Bliss

This inviting 3-bedroom, 2-bath single-family pool home boasts a versatile bonus room perfect for a game room or office, plus a bright sunroom that opens to a private pool. The spacious backyard is ideal for entertaining or relaxing. With lawn and pool maintenance included, enjoy hassle-free living. Conveniently located within excellent school zones, this home is a perfect blend of comfort and convenience.

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2458 Grand Teton Cir #1 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

$3 Bedroom 2 Bathroom Condo In Winter Park

2458 Grand Teton Cir #1, Winter Park, FL 32792

In-unit laundry | Air conditioning | Assigned parking

3 beds

2 baths

$2,200

Condo for rent

Available Feb 15

Stylishly Renovated Condo with Pool & Tennis Courts

This fully renovated 3-bedroom, 2-bathroom condo features a modern design with a heated lanai, brand new appliances, and ceramic flooring. Enjoy community amenities like a clubhouse, pool, and tennis courts. Located just a short walk from shopping essentials, it’s move-in ready and perfect for those seeking comfort and convenience in a peaceful setting. Don't miss this fantastic living opportunity!

651 Trinidad Ct #S - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condominium - WINTER PARK, FL

651 Trinidad Ct #S, Winter Park, FL 32792

In-unit laundry | Walk-in closets | Ceiling fan

1 bed

1 bath

$1,450

Condo for rent

Bright & Spacious End Unit Condo Near Full Sail

This large one-bedroom end unit condo boasts abundant natural light and privacy, all within walking distance to Full Sail University. Featuring fresh paint, ceramic tile throughout, and a spacious living room with a separate dining area, this 759 sq. ft. home is in great condition. Enjoy the convenience of in-unit laundry with a washer and dryer and included water. Perfect for comfortable living in a vibrant community!

101 N Interlachen Ave #102 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

101 N Interlachen Ave #102, Winter Park, FL 32789

In-unit laundry | Air conditioning | Assigned parking

2 beds

2 baths

$1,995

Condo for rent

Charming First-Floor Condo Steps from Park Ave

Experience the allure of this stylish 2-bedroom, 2-bath Lachen House condo, offering 1,148 sq. ft. of living space. Ideal for those who appreciate elegance, it features a fully equipped kitchen, in-unit laundry, and central heat/AC. Enjoy the beautifully landscaped courtyard and trees while being just steps away from Central Park and Park Ave. This pet-friendly residence also includes a reserved carport and amenities like water, sewer, and lawncare, making it a perfect blend of comfort and convenience.

3020 Antique Oaks Cir #132 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

3020 Antique Oaks Cir #132, Winter Park, FL 32792

In-unit laundry | Swimming pool | Residents lounge

2 beds

2 baths

$1,525

Condo for rent

Stylish Condo with Pool Near Full Sail University

Remodeled second-floor 2-bedroom, 2-bath condo offering 1,018 sq ft of modern living. Features include a nice patio, in-unit laundry, and access to a beautiful pool and hot tub. Located in A-rated Winter Park school district, with easy proximity to Park Avenue, Baldwin Park, Winter Park Hospital, and close to Valencia, Rollins College, Full Sail, and UCF. Ideal for those seeking convenience and quality living in a vibrant community. Pet-friendly!

2936 Antique Oaks Cir #71 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

2936 Antique Oaks Cir #71, Winter Park, FL 32792

In-unit laundry | Swimming pool | Dishwasher

2 beds

2 baths

$1,525

Condo for rent

Charming First-Floor Condo with Pool Access

This lovely 2-bedroom, 2-bathroom first-floor condo features spacious living in 1,018 sq ft. Located near Full Sail, it offers a range of amenities including a swimming pool, sauna, and clubhouse. Enjoy the convenience of in-unit laundry and a relaxing jacuzzi. Water, garbage, and sewer services are included in the rent, making this a perfect spot for easy living close to local colleges and healthcare facilities. Dog-friendly for added comfort!

2911 Antique Oaks Cir #12 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

2911 Antique Oaks Cir #12, Winter Park, FL 32792

In-unit laundry | Swimming pool | Hardwood floor

2 beds

2 baths

$1,799

Condo for rent

Modern Condo with Pool Access & Fresh Updates

This beautifully remodeled 2-bedroom, 2-bathroom condo features fresh paint and new wood and ceramic tile flooring throughout. The kitchen boasts granite countertops and new appliances, including a washer and dryer. Enjoy the convenience of a screened patio adjacent to the living and dining areas. Located steps from the pool, this dog-friendly home is perfect for busy lifestyles, with easy access to Full Sail University, UCF, and nearby colleges.

205 Lewfield Cir #205 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condominium - WINTER PARK, FL

205 Lewfield Cir #205, Winter Park, FL 32792

In-unit laundry | Swimming pool | Fitness center

2 beds

2 baths

$1,950

Condo for rent

Charming Ground-Floor Condo with Resort Amenities

This delightful 2-bedroom, 2-bath ground-floor condo offers a perfect Winter Park lifestyle. Enjoy morning coffee on the screened patio overlooking beautiful gardens. The community boasts 2 pools, tennis courts, and a fitness center. Recent upgrades include a new electric panel, washer/dryer, and dishwasher. Just minutes from quaint shops, delicious restaurants, and farmers markets, this home is an ideal blend of comfort and convenience for an active lifestyle.

2021 Canny Cv - Photo 1 of 1
New construction

5d+ ago

Townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

2021 Canny Cv, Winter Park, FL 32792

In-unit laundry | Garage parking | Swimming pool

3 beds

2 baths

$2,700

House for rent

Elegant Townhome with Resort-Style Amenities

This stunning 3-bedroom, 2.5-bath townhome boasts 1,907 sq ft of modern elegance in Grayson Square. Featuring an open-concept living space, a stylish kitchen with stainless steel appliances, and a spacious owner’s suite with a walk-in closet, this home is perfect for entertaining. Enjoy the covered rear lanai, community resort-style pool, and complimentary high-speed internet. Conveniently located near shopping, dining, and major highways, experience the best of Winter Park living.

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2128 Sycamore Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

2128 Sycamore Dr, Winter Park, FL 32789

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

3 beds

2 baths

$2,900

House for rent

Charming Upgraded Home on a Spacious Corner Lot

Move-in ready 3-bedroom, 2-bathroom home featuring 1,760 sq. ft. of stylish space on a .23-acre corner lot. Highlights include a newer septic tank, a durable 2016 roof, and fresh upgrades throughout. Nestled in a highly sought-after school district, it offers an excellent choice for families seeking comfort and convenience. Don’t miss the chance to make this beautifully upgraded residence your own!

428 W Swoope Ave #NA - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

$5,500 Walk to Park Ave!! 4 Bedroom 4 Bathroom Townhouse In Winter Park With Great Amenities

428 W Swoope Ave #NA, Winter Park, FL 32789

In-unit laundry | Air conditioning | Garage parking

4 beds

4 baths

$6,200

$5,500

Price drop

House for rent

Available Feb 15

Luxurious 4-Bedroom Townhouse Steps from Park Ave

Experience upscale living in this stunning 4-bedroom, 4-bathroom townhouse, featuring modern amenities and elegant hardwood floors. Boasting a spacious 2,602 sq ft, the updated kitchen and bathrooms offer convenience and style. Enjoy the comfort of central air and heating, along with in-unit laundry and ample storage. This pet-friendly residence provides a remarkable blend of luxury and practicality, perfect for those seeking vibrant Winter Park living.

1525 Palmer Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

1525 Palmer Ave, Winter Park, FL 32789

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

4 beds

3 baths

$4,695

House for rent

Available Nov 11

Spacious Modern Home with Dual Suites & Fenced Yard

This stunning 4-bedroom, 3-bathroom home boasts 2,300 sqft of bright, inviting space perfect for family living and entertaining. Enjoy a modern kitchen with stainless steel appliances, and two luxurious primary suites with walk-in closets. A fenced backyard offers a private retreat, while ample parking and a convenient laundry room add to the comforts. Located on desirable Palmer Avenue, residents are steps away from Winter Park's energetic downtown, parks, and lakes.

2460 Firstlight Way #2460 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

3 BR, 3 BA in Winter Park

2460 Firstlight Way #2460, Winter Park, FL 32792

In-unit laundry | Walk-in closets | Carpet

3 beds

3 baths

$2,775

House for rent

Available Dec 18

Modern Townhouse with Community Amenities

Enjoy this beautifully designed 3-bedroom, 2.5-bathroom townhouse in a gated community by Lake Howell. The open floor plan features tile flooring, an upgraded kitchen with granite counters and stainless steel appliances, and a spacious primary suite with dual sinks and a walk-in closet. Outdoor highlights include a patio and a quiet backyard area, while community perks offer a pool, cabana, park, and playground. Conveniently located near shopping and dining, this pet-friendly home is perfect for modern living.

7765 Fernbrook Way #7765 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

2 BR, 3 BA in Winter Park

7765 Fernbrook Way #7765, Winter Park, FL 32792

2 beds

3 baths

$1,950

Apartment for rent

Available Dec 21

Refreshing Modern Oasis with Spacious Yard

This beautifully updated 2-bedroom, 3-bath dwelling features new bathrooms, chic ceramic floors, and fresh paint throughout. Enjoy entertaining in the large rear yard, perfect for gatherings. Pet-friendly and conveniently located, this rental offers a vibrant living experience in a serene setting. At 1,200 square feet, it’s designed for comfort and style.

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

$2,800

House for rent

Stylishly Updated Home with Expansive Living Space

This charming 2-bedroom, 1-bath home features hand-scraped wood floors and a modern kitchen with granite counters and sleek appliances. The open layout connects the kitchen, living, and dining areas, perfect for entertaining. Enjoy the expansive covered patio overlooking the backyard, ideal for relaxation. Additional highlights include a spacious primary bedroom with a walk-in closet and a detached garage. Lawn care is included, ensuring a beautiful outdoor space year-round.

3032 Antique Oaks Cir #146 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

3032 Antique Oaks Cir #146, Winter Park, FL 32792

In-unit laundry | Swimming pool | Dishwasher

1 bed

1 bath

$1,350

Condo for rent

Charming Condo with Pool Near Full Sail University

This beautifully remodeled 1-bedroom, 1-bath condo boasts a lovely patio and in-unit laundry. Enjoy resort-style amenities including a pool and hot tub. Located in a prime area with access to A-rated schools, Winter Park Hospital, and major universities like Full Sail and UCF, this condo is perfect for those seeking comfort and convenience. Experience vibrant community living close to Park Avenue and Baldwin Park. Dog-friendly, making it ideal for pet lovers!

1695 Lee Rd #C216 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

1695 Lee Rd #C216, Winter Park, FL 32789

In-unit laundry | Balcony | Assigned parking

3 beds

2 baths

$1,695

Condo for rent

Bright Corner Condo with Pool & Playground Views

Available for immediate move-in, this inviting 3-bedroom, 2-bathroom corner condo boasts serene pool and playground views. Features include a spacious kitchen with pantry, new refrigerator, and convenient in-unit washer and dryer. The fully carpeted interior offers a cozy atmosphere, complemented by a lovely balcony for relaxation. Enjoy quick access to I-4, local dining, and Winter Park Village shopping, making this home a perfect blend of comfort and convenience.

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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

Charming 3-Bed Home with Spacious Garage and Yard

This delightful 3-bedroom, 2.5-bath home spans 1,880 sq. ft., offering a spacious layout perfect for comfortable living. Features include central air for year-round comfort and a garage for added convenience. Enjoy a lovely outdoor space ideal for relaxation or gatherings. Located within a vibrant community, this residence provides a welcoming atmosphere and great potential for those seeking a cozy home.

1957 Canny Cv - Photo 1 of 1
New construction

5d+ ago

Townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

1957 Canny Cv, Winter Park, FL 32792

In-unit laundry | Garage parking | Swimming pool

3 beds

2 baths

$2,800

House for rent

Bright End-Unit Townhome with Resort-Style Amenities

This stunning 3-bedroom, 2.5-bath end-unit townhouse features an open-concept design filled with natural light. Enjoy a modern kitchen with stainless steel appliances and quartz countertops, along with an impressive owner’s suite complete with a walk-in closet and luxurious ensuite. The gated Grayson Square community offers a pool, cabana, high-speed internet, and cable. With a convenient two-car garage, this home is ideally located just minutes from downtown Winter Park and local shopping.

2684 Galliano Cir - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

3 bed 2.5 bath Townhome w 1 car garage

2684 Galliano Cir, Winter Park, FL 32792

In-unit laundry | Garage parking | Carpet

3 beds

2 baths

$2,250

House for rent

Modern Townhouse in Secure Gated Community

This charming 3-bed, 2.5-bath townhouse features a convenient one-car garage in a secure gated community. Enjoy the comfort of in-unit laundry and a stylish kitchen with a dishwasher. The bright living spaces are enhanced by cozy carpets, making this home perfect for relaxation and entertaining. Ideal for those seeking modern living while enjoying community security and amenities.

241 Lewfield Cir - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

241 Lewfield Cir, Winter Park, FL 32792

In-unit laundry | Swimming pool | Dishwasher

2 beds

2 baths

$1,600

Condo for rent

Updated 2-Bed Condo with Private Porch & Pool Access

This freshly renovated 2-bedroom, 2-bathroom condo features a spacious split floor plan, large walk-in closets, and a bright living area. Enjoy modern amenities including a contemporary kitchen and updated bathrooms. A charming porch offers a serene rear view, while the community pool and maintenance-free living add to the appeal. Water, sewer, and lawn care are included, making this pet-friendly home an ideal retreat. Perfect for those ready to move in!

1500 Gay Rd #3B - Photo 1 of 1
3D tour

5d+ ago

Condo for rent in Winter Park

1500 Gay Rd #3B, Winter Park, FL 32789

Carpet | On-site management | Package service

2 beds

2 baths

$1,750

Condo for rent

Available Sep 22

Renovated Lakefront Retreat with Stunning Sunsets

This beautifully renovated 2-bed, 2-bath first-floor end unit offers a serene lakefront lifestyle on Lake Killarney. Enjoy breathtaking sunset views from your deck, and take advantage of the community boat ramp for thrilling water activities. The cozy living and dining area features tile and carpet flooring, while the well-equipped kitchen provides ample space for culinary creations. A covered lanai adds to the outdoor enjoyment, making this a perfect retreat for relaxation and recreation.

3002 Antique Oaks Cir #99 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

3002 Antique Oaks Cir #99, Winter Park, FL 32792

In-unit laundry | Swimming pool | Walk-in closets

1 bed

1 bath

$1,200

Apartment for rent

Available Nov 25

Cozy Apartment with Walk-In Closet & Pet Park Access

This charming 1-bedroom, 1-bath apartment offers a spacious living area and a functional kitchen with full-size appliances. Enjoy the convenience of an in-unit washer and dryer, a bedroom featuring a walk-in closet, and local amenities like a dog park and pool. Nestled in a peaceful Winter Park neighborhood, this affordable home is just minutes away from restaurants, grocery stores, and parks, making it an ideal choice for comfort and convenience.

1575 Lawndale Cir - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1575 Lawndale Cir, Winter Park, FL 32792

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

3 beds

2 baths

$2,600

House for rent

Charming 2-Story Home with Backyard Bliss

This elegant 3-bedroom, 2.5-bath home offers a perfect blend of comfort and style across 1,848 sq ft. Enjoy natural light in spacious living areas with laminate wood and ceramic flooring. Entertain in the sunny backyard or relax in cozy spaces. Conveniently located near schools, shopping, and dining, this home is ready for a new owner to embrace the Florida lifestyle. Washer and dryer included for added convenience!

1973 Canny Cv - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

1973 Canny Cv, Winter Park, FL 32792

In-unit laundry | Swimming pool

3 beds

2 baths

$2,690

House for rent

Modern Townhome with Pool & Special Offer!

This spacious 3-bedroom, 2.5-bath townhouse features 1,907 sq. ft. of comfortable living in a gated community. Enjoy the convenience of in-unit laundry, plus 1 GB Fiber Internet and TV included. Relax by the pool and cabana, all while being just minutes away from Orlando's finest dining, shopping, and attractions. With a holiday special of 1 month free for applications before December 31st, this opportunity is too good to miss!

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1470 Lone Feather Trl - Photo 1 of 1

5d+ ago

House for rent in Winter Park

1470 Lone Feather Trl, Winter Park, FL 32792

In-unit laundry | Air conditioning | Assigned parking

4 beds

3 baths

$4,150

House for rent

Expansive Home with Pool & Modern Comforts

This inviting 4-bedroom, 3.5-bathroom residence spans 2,589 sq ft and offers a serene lifestyle near modern conveniences. Enjoy spacious bedrooms, well-appointed baths, and year-round comfort with central air and heating. The property features a refreshing swimming pool and a courtyard, perfect for relaxation. Located just minutes from shopping and AdventHealth Orlando, this home combines comfort and convenience for a delightful living experience.

1931 Carrigan Ave #1931 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

3 BR, 2 BA in Winter Park

1931 Carrigan Ave #1931, Winter Park, FL 32792

In-unit laundry | Air conditioning | Outdoor space

3 beds

2 baths

$2,200

Apartment for rent

Available Feb 13

Newly Renovated Home with Spacious Fenced Yard

This beautifully renovated 3-bedroom, 2-bath home offers ample space, set on an oversized lot with a fully fenced backyard, perfect for entertaining. With new AC, plumbing, and electric systems, this home also features washer/dryer hookups and a prime location just 7 minutes from Park Ave’s shopping and dining. Ideal for families and pet owners seeking comfort and convenience near A+ schools. Perfect for those who want a fresh start!

3007 Ash Park Pt #3007 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

2 BR, 2 BA in Winter Park

3007 Ash Park Pt #3007, Winter Park, FL 32792

Outdoor space

2 beds

2 baths

$2,195

Apartment for rent

Available Dec 9

Bright & Spacious 2BR Retreat with Fenced Yard

This charming 2-bedroom, 2-bath home features an inviting open layout with plenty of natural light and spacious living areas. Ideal for comfort and privacy, both bedrooms come with their own bathrooms. Enjoy a two-car garage and a fully fenced backyard, perfect for pets and outdoor relaxation. Located in a desirable neighborhood, this home is conveniently close to top-rated schools, parks, shopping, and dining spots. Move-in ready and waiting for you!

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

Charming Ground-Floor Condo Steps from Park Avenue

This beautifully remodeled 2-bedroom, 2-bathroom condo features new laminate flooring and a stunning gourmet kitchen. Enjoy spacious bedrooms with ample closet space and a lovely courtyard off the back for outdoor relaxation. With one reserved covered parking space and located just a block from the vibrant dining and shopping of Park Avenue, this downtown Winter Park gem offers convenience and style in a desirable setting.

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

Charming Cape Cod Retreat Near Lake Mizell

This delightful 2-bedroom, 2-bath Cape Cod-style home offers 1,393 sq ft of inviting living space in Winter Park. Enjoy beautiful hardwood floors, quartz countertops, and spacious bedroom suites. The sunlit sunroom and private screened-in porch provide perfect spots for relaxation. Just one block from Lake Mizell and close to dining and shopping, this pet-friendly rental includes a saltbox detached garage with laundry facilities, making it a wonderful opportunity for your next home.

650 Trinidad Ct - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

650 Trinidad Ct, Winter Park, FL 32792

In-unit laundry | Swimming pool | Fitness center

2 beds

2 baths

$1,750

Condo for rent

Available Dec 16

Vibrant 2-Bedroom Condo with Community Amenities

This inviting 2-bedroom, 2-bath condo offers spacious living across two levels, perfect for roommates. Enjoy the benefits of a vibrant community with a refreshing pool, well-equipped gym, and tennis courts. Located in the heart of Winter Park, it promises a comfortable lifestyle with modern conveniences. Also includes an option for a security deposit-free lease. Make this your home today and embrace the Winter Park way of living!

1622 Arbor Park Dr #1 - Photo 1 of 1

5d+ ago

House for rent in Winter Park

1622 Arbor Park Drive - 1

1622 Arbor Park Dr #1, Winter Park, FL 32789

Ceiling fan | Controlled access

3 beds

1 bath

$2,500

House for rent

Available Oct 10

Bright & Spacious Home with Large Fenced Yard

This inviting 3-bed, 1.5-bath residence spans 1,351 sq. ft. and offers a large living room bathed in natural light, connecting to a spacious backyard with a deck. Enjoy the tranquility of the fenced yard bordered by a serene watercourse. Conveniently located near schools, parks, and restaurants, this pet-friendly home comes with a washer/dryer and boasts no HOA. With a move-in incentive of $500 for a December move, it’s a perfect opportunity for a fresh start!

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

Award-Winning Architectural Marvel with Pool

This stunning custom residence spans 5,164 sq ft and showcases 5 bedrooms and 6 bathrooms, redefining luxury living with state-of-the-art technology and artful design. Highlights include a floating staircase, expansive outdoor living space with a resort-style pool, and a tranquil primary suite. Located in the desirable Virginia Heights neighborhood, this home offers deeded lake access and is a short stroll from Winter Park’s dining and shopping, embodying elegance and modern sophistication.

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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

Modern Townhome with Luxury Finishes & Smart Features

This stunning 3-bedroom, 2.5-bath townhome radiates coastal charm and modern efficiency in an open-concept design. Highlights include a gourmet kitchen with quartz countertops, a spacious primary suite with a designer bath, and a private courtyard for outdoor entertaining. With features like smart home technology and a WiFi-enabled garage, this immaculate residence ensures comfort and convenience just minutes from dining and shopping in vibrant Winter Park.

1807 N Park Ave #1807 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

3 BR, 2 BA in Winter Park

1807 N Park Ave #1807, Winter Park, FL 32789

Assigned parking | Outdoor space

3 beds

2 baths

$3,295

Apartment for rent

Available Jul 11

Private Oasis with Pool & Spacious Living

This beautifully maintained 3-bedroom, 3-bathroom home boasts 1,747 sq. ft. of bright, open living space. Each bedroom offers its own bath for added convenience. Enjoy entertaining in the fully fenced backyard with a sparkling private pool. An attached 2½-car garage and extra driveway parking spaces add practicality to this charming residence. Set in a prime Winter Park area, it's close to parks, shopping, dining, and top-rated schools, making it ideal for families and pets.

519 Park North Ct - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

519 Park North Ct, Winter Park, FL 32789

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

4 beds

3 baths

$7,000

House for rent

Elegant Single-Story Oasis with Private Pool

Experience luxurious comfort in this stunning four-bedroom, three-and-a-half-bath home offering 3,302 sq. ft. of refined living space. The open layout connects a gourmet kitchen with granite counters to a cozy family room, leading to a screened patio and private pool. Enjoy a relaxing primary suite with an expansive en suite bath and custom closet. Beautiful Brazilian cherry wood floors, crown molding, and high ceilings enhance the elegant ambiance. Monthly rent includes grounds care and pool maintenance for a hassle-free lifestyle.

3055 Autumn Ct #3055 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

3 BR, 2 BA in Casselberry

3055 Autumn Ct #3055, Winter Park, FL 32792

Carpet | Outdoor space

3 beds

2 baths

$2,275

Apartment for rent

Available Nov 10

Modern Village Home with Fenced Backyard Retreat

This charming 3-bed, 2-bath village-style home offers an open-concept layout with stainless steel appliances and sleek laminate flooring. Cozy carpet in the bedrooms enhances comfort, while the fenced backyard provides a private outdoor space ideal for relaxation. Conveniently located near top-rated schools, shopping, and major roads, this residence is ready for comfortable living in the heart of Winter Park.

3060 George Mason Avenue #N10C - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

3060 George Mason Avenue #N10C, Winter Park, FL 32792

In-unit laundry | On-site laundry | Balcony

1 bed

1 bath

$1,300

Condo for rent

Bright & Charming Condo with Private Balcony

This updated 1-bedroom, 1-bath condo features an open layout with abundant natural light and modern cabinetry in the kitchen. Enjoy in-unit laundry and a private balcony for outdoor relaxation. Ideally located near Full Sail University and UCF, this 803 sq ft home offers convenience for residents and investors alike in a vibrant community.

2553 Galliano Cir - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

2553 Galliano Cir, Winter Park, FL 32792

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

3 beds

2 baths

$2,000

House for rent

Elegant Townhome with Screened Lanai Retreat

Experience comfort in this stylish 3-bedroom, 2.5-bath townhouse spanning 1,628 sq ft. Nestled in a gated community, this residence features a convenient laundry area and a one-car garage. Enjoy serene outdoor living on the screened-in lanai and explore beautiful walking paths nearby. The high ceilings and central air add to the home's inviting atmosphere, making it perfect for both relaxation and entertaining in the vibrant Winter Park area.

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

Elegant Townhome with Smart Features & Courtyard

This stunning 3-bedroom, 2.5-bath townhome features an open-concept design, high ceilings, and stylish finishes throughout. The gourmet kitchen boasts waterfall quartz countertops and stainless steel appliances. A private walled courtyard is perfect for outdoor entertaining, while the spacious primary suite includes a luxurious bath and walk-in closet. Built for modern living with smart-home technology, this immaculately maintained residence offers convenience near vibrant local attractions.

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Updated: February 11, 2026

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Learn more about renting in Winter Park, FL

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Local insights: What it's like to live in Winter Park, FL

Winter Park, FL, offers a blend of beautiful parks and lakes, making it a pleasant place for outdoor activities like jogging and biking. Residents appreciate the vibrant local arts scene, with frequent events and galleries to explore. The area is noted for its excellent schools, which is a significant draw for families. However, some locals mention frustrations with traffic and parking, especially around the popular Park Avenue shopping district, where congestion can be a hassle during peak times.

How much is the average rent in Winter-Park, FL for 1-bedroom and 2-bedroom apartments?

The median rent for a one-bedroom apartment in Winter Park, FL is $1,349, while a two-bedroom apartment averages $1,649.

Are rents going up or down in Winter-Park, FL?

Rents in Winter Park, FL have experienced a slight decline in 2024, with average monthly rents decreasing by 3.1% year-over-year.

When is the best time to look for an apartment in Winter-Park, FL?

The best time to look for an apartment in Winter Park, FL is during the less competitive months of April and January, when prices may be lower, although the selection might be limited.

Are there pet-friendly apartments in Winter-Park, FL?

Yes, approximately 62% of the listings in Winter Park, FL are pet-friendly with some restrictions.

Are utilities usually included in rent in Winter-Park, FL?

Only about 11% of the listings in Winter Park, FL include utilities in the rent.

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.

Looking for apartments in Winter Park, FL near you?

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💰Best rent deal3002 Antique Oaks Cir #99
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