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Apartments for Rent in Winter Park, FL

230 rentals

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

$10,500

Apartment for rent

Available May 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.

7421 Daniel Webster Dr #A - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

7421 Daniel Webster Dr #A, Winter Park, FL 32792

On-site laundry | Swimming pool | Concierge service

1 bed

1 bath

$1,250

Condo for rent

Available May 22

Bright & Breezy Condo with Serene Courtyard Views

This charming first-floor condo offers 809 sq ft of cozy living space with 1 bedroom and 1 bath. The open-concept design showcases tile flooring and a bright living area. Enjoy your mornings in the screened lanai overlooking the peaceful courtyard. Residents have access to a community pool and clubhouse, all while being conveniently situated near shopping and dining. Pet-friendly and perfect for those seeking affordable, comfortable living in Central Florida!

2433 Firstlight Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

2433 Firstlight Way, Winter Park, FL 32792

In-unit laundry | Garage parking | Swimming pool

3 beds

2.5 baths

$2,900

House for rent

Stylish Townhome with Modern Comforts & Community Perks

This stunning 3-bedroom, 2.5-bathroom townhouse offers 2,308 sqft of modern living within the gated Enclave at Hawks Crest. Enjoy an open living area, sleek kitchen with stainless steel appliances, and a cozy flex room ideal for a home office. The primary suite features tray ceilings and an en-suite bath. Additional highlights include a loft area, garage parking, and a covered patio. Residents will love the community pool and playground, plus internet & cable included!

2471 Waving Moss Way - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Winter Park Pool Home in the Landings at Hawks Crest!!

2471 Waving Moss Way, Winter Park, FL 32792

In-unit laundry | Furnished | Dishwasher

4 beds

3 baths

$3,695

House for rent

Available Jun 1

Elegant Pool Home with Resort-Style Amenities

A stunning 4-bedroom, 3-bath home featuring a private pool within the gated Landings at Hawks Crest community. This spacious 2,196 sq ft residence offers contemporary designs for effortless living and entertaining. Enjoy access to resort-style amenities, including a community pool, fitness center, and fishing pier. The home can be rented furnished or unfurnished, with lawn and pool services included, making it a perfect place for comfortable Florida living.

1931 Carrigan Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

1931 Carrigan Ave, Winter Park, FL 32792

Air conditioning | Central heat | Dishwasher

3 beds

2 baths

$2,095

House for rent

Newly Renovated Home with Spacious Backyard Oasis

This charming 3-bedroom, 2-bath residence features fresh renovations and sits on an oversized, fully fenced lot, perfect for outdoor fun. Enjoy central AC, washer/dryer hookups, and proximity to A+ schools and Park Avenue's vibrant shopping and dining. An excellent choice for comfort and convenience, this pet-friendly home is ready for its next residents!

1625 Tioga Trl - Photo 1 of 1

5d+ ago

House for rent in Winter Park

1625 Tioga Trl, Winter Park, FL 32789

Air conditioning | Garage parking | Swimming pool

4 beds

3 baths

$4,195

House for rent

Spacious Home with Pool in a Desirable Locale

This inviting 4-bedroom, 3-bathroom residence boasts a split floorplan, open living spaces, and an idyllic outdoor oasis with a screened porch and sparkling pool. Enjoy wood flooring throughout and a well-equipped kitchen featuring white cabinets and a breakfast nook. Perfectly located in a sought-after school district near parks, shopping, and dining, this home combines comfort and convenience for enjoyable living. Regular pool service is included.

2379 Flamingo Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

2379 Flamingo Way, Winter Park, FL 32792

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

3 beds

2 baths

$2,400

House for rent

Stunning Townhome with Resort-Style Amenities

This beautifully maintained 3-bedroom, 2-bathroom townhome features an open-concept layout and stylish tile flooring. Enjoy entertaining in the spacious kitchen with granite countertops. The primary suite is a private retreat with dual walk-in closets and an ensuite bath, while two additional bedrooms offer versatility. Delight in community amenities like tennis courts, pools, and a clubhouse, all just minutes from Park Avenue and top local universities. Embrace vibrant living in a prime location!

1947 Summerfield Rd - Photo 1 of 1

5d+ ago

House for rent in Winter Park

3 beds

2 baths

$2,649

House for rent

Available Apr 17

Comfortable Family Home Near Winter Park Attractions

Ideal for immediate move-in, this welcoming 3-bedroom, 2-bath home offers a spacious layout with well-appointed rooms and a lovely kitchen filled with counter and cabinet space. Enjoy convenient access to downtown Winter Park, Crosby Center, and Cady Way Park. Pet-friendly and equipped with on-site management, this property is perfect for families seeking comfort and convenience. Don't miss out on this opportunity!

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520 Holt Ave - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

College Quarters - 520 Holt Ave

520 Holt Ave, Winter Park, FL 32789

In-unit laundry | Dishwasher | Outdoor space

1 bed

1 bath

$1,950

Apartment for rent

Available Jun 1

Charming Cottage Steps from Rollins College

This delightful one-bedroom, one-bathroom cottage offers modern living just a five-minute walk from Rollins College and vibrant Park Avenue. Featuring a newly-renovated interior, it boasts high-quality appliances, an upgraded bathroom, and an in-unit washer and dryer. Enjoy the convenience of off-street parking and your own private entry porch. Rent includes sewer, water, and garbage, making this an ideal blend of comfort and location.

1409 Lone Feather Trl - Photo 1 of 1

5d+ ago

House for rent in Winter Park

1409 Lone Feather Trl, Winter Park, FL 32792

In-unit laundry | Swimming pool | Microwave

4 beds

3.5 baths

$3,895

House for rent

Modern Family Home in Exclusive Gated Community

This stunning 4-bedroom, 3.5-bathroom home features a beautiful tile roof and an inviting open-concept layout. With a soaring 20-foot ceiling in the family room and wide sliding doors leading to a spacious covered lanai, it’s the perfect space for gatherings. Enjoy big-ticket upgrades like UV sanitizing lights in bathrooms and a water filter system in the kitchen. The community offers fantastic amenities, including a pool, clubhouse, and dog park, all while being minutes from shopping and dining.

3012 Patel Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

2 beds

2 baths

$1,600

House for rent

Cozy Home with Fenced Yard & Convenient Location

This charming 2-bedroom, 2-bath home features a spacious kitchen and living area, all set within 967 sq ft of tiled comfort. Enjoy an accommodating driveway for two cars and a fenced backyard with a small shed, perfect for pets or outdoor activities. Located near shopping options like Target and Publix, plus the highly-rated Winter Park Schools, this home combines convenience with a welcoming atmosphere.

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1000 S Semoran Blvd #806 - Photo 1 of 1

5d+ ago

Golfside condo for rent in Winter Park

Nice 2 Bedroom 2 Bath Condo! Golfside Villas! Apply Today!

1000 S Semoran Blvd #806, Winter Park, FL 32792

In-unit laundry | Air conditioning | On-site laundry

2 beds

2 baths

$1,495

Condo for rent

Available Apr 13

Charming Condo with Pool and Modern Amenities

Enjoy this inviting 2-bedroom, 2-bathroom condo featuring an open floor plan and cozy living area. This pet-friendly unit includes water, in-unit laundry, and a lovely breakfast bar. Residents can relax by the community pool and appreciate the convenient location. With 1,045 sq. ft. of comfortable living space, this home is ready for immediate move-in, making it a perfect choice for anyone looking for style and convenience.

1041 Tuscany Pl - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1041 Tuscany Pl, Winter Park, FL 32789

In-unit laundry | Garage parking | Swimming pool

4 beds

3.5 baths

$12,000

House for rent

Elegant Home with Scenic Views & Luxurious Touches

Nestled in a tranquil neighborhood, this stunning 4-bedroom, 3.5-bath residence spans 3,064 sq ft and features an open floor plan highlighted by soaring vaulted ceilings and abundant natural light. The gourmet kitchen boasts premium Wolf appliances and quartz countertops, while the primary suite offers a spa-inspired bath with a luxurious walk-in shower. Outdoor spaces include a spacious deck overlooking the pool, hot tub, and beautifully landscaped backyard, perfect for embracing resort-style living.

5523 Cretan Way - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Single Family Residence - WINTER PARK, FL

5523 Cretan Way, Winter Park, FL 32792

In-unit laundry | Assigned parking | Central heat

3 beds

2 baths

$2,195

House for rent

Charming Townhouse in Tranquil Cul-de-Sac Setting

Experience comfort in this delightful 3-bedroom, 2-bath townhouse featuring a private driveway in a peaceful neighborhood. Enjoy modern amenities like central air, a fully-equipped kitchen, and a mini bar, alongside a yard and storage shed. Lawn service is included, while the Resident Benefits Package adds value with liability insurance, identity theft protection, and more, making living here both convenient and secure.

1026 S Lakemont Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1026 S Lakemont Ave, Winter Park, FL 32792

In-unit laundry | On-site laundry | Swimming pool

3 beds

2 baths

$4,300

House for rent

Upgraded Pool Home with Outdoor Entertaining Spaces

Experience effortless living in this beautifully upgraded 3-bedroom, 2-bath pool home. Featuring an open floor plan and a spacious kitchen with modern finishes, this residence shines with ample outdoor entertaining space including a screened-in pool, covered patio, and firepit lounge. Located in a top-rated school zone and close to local amenities, this home balances lifestyle and convenience in a vibrant Winter Park setting.

303 Sandlewood Trl #2 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Gorgeous, Completely Remodeled 2/2.5 Condo in Sandlewood Creek- Winter Park!

303 Sandlewood Trl #2, Winter Park, FL 32789

In-unit laundry | On-site laundry | Swimming pool

2 beds

2.5 baths

$1,900

Condo for rent

Charming Two-Story Condo with Modern Flair

This beautifully renovated 2-bedroom, 2.5-bath condo features stylish gray-toned laminate flooring throughout, creating a contemporary vibe. The updated kitchen boasts stainless steel appliances and leads to a screened back porch. Upstairs, both spacious bedrooms offer ample closet space and ceiling fans. Enjoy the community pool and unbeatable location near top-rated schools and shopping. Perfect for those seeking stylish and convenient living in Winter Park!

138 Lewfield Cir - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

138 Lewfield Circle - .

138 Lewfield Cir, Winter Park, FL 32792

Outdoor space

1 bed

1 bath

$1,250

Condo for rent

Available Apr 1

Cozy Second-Floor Condo with Private Balcony

This charming 1-bedroom, 1-bath condo spans 678 sq ft and features a spacious open layout. Enjoy cozy living with access to a private balcony overlooking a serene view. Perfectly situated in a tranquil neighborhood, this home offers great community amenities including a sparkling pool and clubhouse. Conveniently located near shopping, dining, and top-rated schools, this delightful condo is a perfect blend of comfort and accessibility in the Lake Howell community.

1776 Mondrian Cir - Photo 1 of 1
New construction

5d+ ago

Townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

1776 Mondrian Cir, Winter Park, FL 32789

In-unit laundry | Garage parking | Hardwood floor

3 beds

3.5 baths

$5,500

House for rent

Luxurious Waterfront Townhome with Outdoor Spaces

Experience modern luxury in this stunning 3-bedroom, 3.5-bath waterfront townhome featuring an expansive layout with 2,193 sq ft of elegance. Bright interiors boast soaring 10'6" ceilings and stylish kitchens with high-end Samsung appliances. Enjoy a private terrace with partial lake views, an outdoor patio for entertaining, and access to community amenities like kayak racks. With its prime location near downtown Winter Park and Lake Killarney, this residence blends comfort and convenience perfectly.

2530 Passamonte Dr #10E - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Condominium - WINTER PARK, FL

2530 Passamonte Dr #10E, Winter Park, FL 32792

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

3 beds

2.5 baths

$2,600

House for rent

Charming Townhome with Scenic Water Views

This beautifully remodeled 3-bedroom, 2.5-bath townhouse offers fresh interior updates, including new flooring and paint. Enjoy serene water views from the patio, and take advantage of nearby amenities like a dog park and children's play area. Ideally located just outside Baldwin Park, this home provides easy access to shopping and top schools, making it perfect for families. Unfurnished and ready for move-in by mid-April, it combines comfort and convenience in a welcoming community.

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1721 Shasta Ct - Photo 1 of 1

5d+ ago

House for rent in Winter Park

3 Bedroom Pet-Friendly Home in WINTER PARK, FL with Main Street Renewal

1721 Shasta Ct, Winter Park, FL 32792

Swimming pool

3 beds

2 baths

$2,675

House for rent

Charming Pet-Friendly Retreat with Pool Access

This beautiful 3-bedroom, 2-bath home offers 1,525 sq ft of inviting space, perfect for families and pet lovers. Enjoy the convenience of a swimming pool, making it an ideal spot for relaxation and fun. With a pet-friendly policy and easy application process, this residence is ready for new tenants! The home features a welcoming atmosphere and is well-suited for comfortable living in a vibrant community.

7429 Daniel Webster Dr - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condo for rent

Charming Fully Furnished Condo in Winter Park

Embrace the vibrant lifestyle in this enchanting fully furnished 2-bed, 2-bath condo. Measuring 1,036 sq ft, this beautifully maintained unit features upgraded fixtures and abundant natural light. Enjoy modern amenities, including a kitchen with new granite countertops and in-unit washer/dryer. Conveniently located near attractions like Disney and Cocoa Beach, plus easy access to major routes and local colleges. Rent special includes $100 credit for the first three months!

3036 Patel Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

House for rent

Bright 3-Bed Home with Huge Screened Patio

Available May 1st, this charming 3-bedroom, 2-bath house features an open-concept layout with easy-to-maintain tile flooring throughout. Enjoy the spacious living area that flows into a gigantic screened patio overlooking a private wooded backyard, perfect for relaxation. Nestled on a cul-de-sac and just minutes from Full Sail, this home also includes a privacy fence and attached one-car garage, making it an ideal serene retreat.

1508 Florentino Ln - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

1508 Florentino Ln, Winter Park, FL 32792

In-unit laundry | Garage parking | Fitness center

2 beds

2.5 baths

$2,350

House for rent

Modern Townhome with Loft & Screened Patio Retreat

This charming 2-bedroom, 2.5-bath townhouse features a spacious layout enhanced by high ceilings and modern upgrades. The kitchen boasts granite countertops and stainless steel appliances, while a large loft adds versatility. Enjoy relaxing in the screened patio, seamlessly connecting indoor and outdoor living. Located in a gated community, this residence offers convenience just minutes from dining, shopping, and downtown Winter Park. Perfect for those seeking comfort and style!

2115 Sycamore Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

2115 Sycamore Dr, Winter Park, FL 32789

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

4 beds

2 baths

$3,500

House for rent

Mid-Century Delight with Lush Outdoor Oasis

This updated 4-bed, 2-bath mid-century home features an expansive .34-acre lot with a botanical garden and a serene patio with a raised hot tub. The open-concept great room offers a bright space with a wood-burning fireplace, while the kitchen boasts granite counters and a reverse osmosis water filtration system. Enjoy the master suite's spacious walk-in closet and convenient access to the scenic backyard. Located near Baldwin Park and top-rated schools, it's perfect for family living.

1521 Chestnut Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1521 Chestnut Ave, Winter Park, FL 32789

Garage parking | Balcony | Swimming pool

4 beds

3 baths

$6,500

House for rent

Modern Family Home with Private Pool Paradise

This stunning 4-bedroom, 3-bathroom home, built in 2023, offers a perfect blend of modern luxury and functional elegance. Boasting an open-concept layout with a designer kitchen, light-filled living room, and a spacious dining area, it's designed for today's lifestyle. Enjoy the private in-ground pool, fenced yard, and oversized balcony overlooking the serene outdoor space. Located steps from Phelps Park and minutes from Park Avenue's shops and dining, this residence is truly exceptional.

1803 Pineview Cir - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1803 Pineview Cir, Winter Park, FL 32792

In-unit laundry | Hardwood floor | Ceiling fan

2 beds

1 bath

$1,975

House for rent

Refurbished Winter Park Home with Open Yard

This charming 2-bedroom, 1-bathroom home spans 1,029 sq ft and has been beautifully refurbished. Featuring wood flooring throughout and a modern kitchen with newer cabinets, this property includes a single car carport, washer/dryer, and ample outdoor space. Enjoy a large open yard for relaxation, with lawn care included for convenience. Perfect for anyone seeking comfort and style in Winter Park!

151 N Orlando Ave #118 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

151 N Orlando Ave #118, Winter Park, FL 32789

In-unit laundry | Swimming pool | Ceiling fan

3 beds

2 baths

$2,500

Condo for rent

Lakefront Condo with Scenic Sunsets & Pool Access

This tranquil 2-bed, 1-bath condo offers stunning lakefront views in the serene Lake Killarney Condos. Enjoy 710 sq. ft. of comfortable living space, complete with a community pool and lush grassy areas. Conveniently located near local shops, restaurants, and entertainment, this property presents a perfect investment opportunity or a dream retreat in Winter Park.

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2711 Aloma Ave - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

3 beds

2 baths

$2,015

Apartment for rent

Available Apr 27

Charming 3-Bed Apartment with Modern Comforts

This inviting 3-bedroom, 2-bathroom apartment is designed for comfort and style, boasting 1,175 square feet of living space. With a pet-friendly policy, it offers a welcoming atmosphere. Perfect for those seeking a cozy and convenient lifestyle. Don’t miss out on this upcoming opportunity!

540 W Comstock Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

540 W Comstock Ave, Winter Park, FL 32789

Ceiling fan

3 beds

1 bath

$2,900

House for rent

Charming Renovated Home in Prime Winter Park Area

This newly renovated 3-bedroom, 1-bath home offers a stylish and comfortable living experience. Located just minutes from Park Avenue, enjoy modern finishes in a clean, move-in ready space. With 1,056 square feet of functional layout, this property combines accessibility and neighborhood charm, making it perfect for families and professionals alike in vibrant Winter Park. Don't miss out on this high-demand rental opportunity!

3032 Antique Oaks Cir #145 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condominium - WINTER PARK, FL

3032 Antique Oaks Cir #145, Winter Park, FL 32792

In-unit laundry | Swimming pool | Dishwasher

1 bed

1 bath

$1,400

Condo for rent

Cozy 1-Bed Condo with Poolside Charm

This inviting 1-bedroom, 1-bath condo offers an open layout with fresh interior paint and convenient in-unit laundry. Relax on the screened patio or enjoy the community pool and clubhouse at Parkview Village. Perfect for students or professionals, located near UCF and Full Sail University.

3075 Aaron Burr Ave #Q8B - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

1 bed

1 bath

$1,200

Condo for rent

Charming 1-Bed Condo with Pool Access

This delightful 1-bedroom, 1-bath condominium offers a move-in ready retreat with all-tiled flooring, fresh paint, and new appliances. Enjoy your rear balcony overlooking the pool, perfect for relaxation. The community features a large swimming pool and a laundry facility. Located near Full Sail University and UCF, with easy access to shopping, dining, and schools. A fully furnished option is available, making this a prime choice for students and professionals alike!

1814 Barker Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1814 Barker Dr, Winter Park, FL 32789

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

5 beds

4 baths

$11,000

House for rent

Luxurious Modern Marvel with Private Pool Oasis

Experience luxury in this stunning 5-bedroom, 4-bath home boasting 4,100 sq ft of modern living. Sleek architecture and abundant light enhance the chef's kitchen and spacious living areas, which flow seamlessly into a resort-style lanai and private backyard with a sparkling pool. The first-floor primary suite features a spa-like bath, while upstairs offers a loft and four more bedrooms. Minutes from vibrant Park Avenue, this home is perfect for stylish entertaining and comfortable living.

7454 Wynnewood Sq #188 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

7454 wynnewood circle - 188

7454 Wynnewood Sq #188, Winter Park, FL 32792

3 beds

2.5 baths

$1,950

House for rent

Available Apr 1

Spacious 3-Bed Townhome with Ample Storage

This inviting townhouse features 3 bedrooms and 2.5 baths, offering plenty of space for comfortable living. Ideal for those seeking a vibrant lifestyle, it includes washer/dryer connections and lots of storage throughout. Enjoy a well-designed layout perfect for modern living. Pet restrictions apply.

1441 Oneco Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

1441 Oneco Ave, Winter Park, FL 32789

In-unit laundry | Air conditioning | Garage parking

4 beds

3.5 baths

$6,000

House for rent

Stylish Modern Home with Spacious Living Areas

This stunning 4-bedroom, 3.5-bathroom home features numerous upgrades and a spacious layout, ideal for entertaining. The gorgeous kitchen shines with solid wood cabinets, granite counters, and a gas stove, flowing into a bright family room. Enjoy hardwood floors, a bonus loft, and an exquisite primary suite that opens to a private balcony. The fenced yard and covered patio complete this beautiful family oasis, conveniently located near parks, shops, and top-rated schools.

3075 Aaron Burr Ave #C - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

1BR/1.0BA

3075 Aaron Burr Ave #C, Winter Park, FL 32792

On-site laundry | Dishwasher | Microwave

1 bed

1 bath

$1,200

Condo for rent

Cozy Condo Retreat Near Winter Park's Best

Embrace the charm of this pet-friendly 1-bedroom, 1-bath condo. With 537 square feet of thoughtfully designed space, it features modern appliances including a microwave and dishwasher, ensuring convenience and comfort. Onsite laundry adds to the ease of living. Perfectly situated near Winter Park's vibrant offerings, this condo is an ideal retreat for those seeking a blend of cozy living and accessibility. Enjoy the Florida lifestyle in this inviting space!

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1667 Mizell Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

1667 Mizell Ave, Winter Park, FL 32789

Dishwasher | Outdoor space | Oven

3 beds

3 baths

$3,995

House for rent

Charming Home with Lush Backyard Oasis

This delightful 3-bedroom, 3-bathroom residence combines comfort and style in a warm, inviting space. Detailed archways and bright living areas enhance its charm, while a modern kitchen with stainless steel appliances is perfect for culinary adventures. The expansive private backyard features a paved area, ideal for relaxing or entertaining. Conveniently located near shopping and dining, this home offers the best of Winter Park living. Lawn care included for added ease.

3050 Autumn Ct - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

3050 Autumn Ct, Winter Park, FL 32792

In-unit laundry | On-site laundry | Swimming pool

3 beds

2 baths

$1,950

Condo for rent

Available Mar 27

Charming Corner Condo with Pool Access in Winter Park

This delightful 3-bedroom, 2-bath condo offers tile and laminate flooring throughout and features an in-unit washer and dryer for added convenience. Enjoy outdoor living on the covered back patio, complete with storage. Located on a spacious corner lot, this pet-friendly home also grants access to a refreshing community pool. Experience comfort and community living at a reduced price of $1,950/month—schedule a showing today!

110 Killarney Bay Ct #1 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condominium - WINTER PARK, FL

110 Killarney Bay Ct #1, Winter Park, FL 32789

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

2 beds

2 baths

$2,550

Condo for rent

Charming Lakefront Condo with Spacious Layout

Embrace serene lakefront living in this beautifully maintained 2-bedroom, 2-bath condo, featuring an open-concept design and abundant natural light. The well-appointed kitchen blends with generous living and dining areas, ideal for entertaining. Enjoy a private primary suite with en-suite bath and ample storage. Located near Downtown Winter Park and Interstate 4, this home combines comfort and convenience with access to community amenities.

782 S Pennsylvania Ave #1 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condominium - WINTER PARK, FL

782 S Pennsylvania Ave #1, Winter Park, FL 32789

In-unit laundry | Garage parking | Ceiling fan

3 beds

2.5 baths

$5,490

Condo for rent

Bright & Spacious Condo with Modern Amenities

This charming 3-bedroom, 2.5-bath condo features a generous 2,354 sq. ft. of living space filled with natural light. Enjoy a sleek modern kitchen with updated appliances, spacious bedrooms, and the convenience of in-unit laundry. Residents benefit from well-maintained community amenities and a prime location near shopping, dining, and entertainment options. Perfect for those seeking comfort and accessibility in vibrant Winter Park!

520 N Orlando Ave #105 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

In-unit laundry | Fitness center | Storage

1 bed

1 bath

$1,695

Apartment for rent

Available Mar 12

Trendy Two-Level Loft in Vibrant Winter Park

Experience modern urban living in this stylish 1-bed, 1-bath loft featuring a unique two-level layout. Spacious high ceilings and oversized windows offer a bright, inviting atmosphere. Enjoy access to amenities like a fitness center, bike storage, and a community lounge. Located in the heart of Winter Park Village, residents are steps away from shopping, dining, and entertainment. Plus, with pet-friendly options available, it's perfect for furry companions!

1807 N Park Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

House for rent

Serene Home with Pool & Office in Winter Park

This beautifully maintained 3-bed, 3-bath home offers 1,747 sq. ft. of open living space, complete with a dedicated office, ideal for remote work. Enjoy a fully fenced backyard featuring a sparkling pool perfect for relaxation or entertainment. The property includes an attached garage and ample parking, with lawn care and pool service included. Nestled in a coveted neighborhood, this pet-friendly residence is close to parks and amenities, offering convenience for the whole family.

1235 Via Estrella - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1235 Via Estrella, Winter Park, FL 32789

In-unit laundry | Garage parking | Swimming pool

4 beds

3 baths

$5,895

House for rent

Spacious 4-Bed Home with Pool & Spa Oasis

Lease this stunning 4-bedroom, 3-bath residence featuring an open-concept layout and beautiful bamboo wood floors. The well-equipped kitchen and sunken family room overlook a sparkling pool and heated spa in your private backyard. Enjoy the convenience of a full pool bath and an attached garage. Situated near the prestigious Winter Park Racquet Club, this 2,207 SF home offers a fantastic Florida lifestyle with lawn and pool care included.

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

$2,250

Condo for rent

Available Apr 4

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!

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1815 Barker Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1815 Barker Dr, Winter Park, FL 32789

In-unit laundry | Furnished | Ceiling fan

4 beds

2 baths

$4,000

House for rent

Luxury Lake-View Retreat with Outdoor Paradise

This stylish 4-bedroom, 2-bath home features an open-concept design adorned with curated artwork, lush gardens, and a spacious wood deck with an outdoor kitchen, perfect for entertaining. Enjoy stunning lake views and proximity to Orlando's attractions and cultural sights. Ideal for families or professionals seeking a refined long-term stay—embrace an active lifestyle with nearby walking trails, tennis courts, and golf clubs.

952 Fairway Dr - Photo 1 of 1

5d+ ago

Golfside house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

952 Fairway Dr, Winter Park, FL 32792

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

3 beds

2 baths

$3,300

House for rent

Stunning Home with Luxurious Upgrades Throughout

Experience unparalleled craftsmanship in this exquisite 3-bedroom, 2-bathroom home, boasting over 2,000 sq. ft. of elegant living space. Highlights include a state-of-the-art kitchen with stainless appliances, a cozy family room with a fireplace, and a serene screened sunroom. The luxurious master suite features a spa-like bath, while the beautifully landscaped outdoor space and deck are ideal for entertaining. Enjoy the convenience of in-unit laundry and a double garage.

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

$1,800

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.

Leeward Way #C110 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condominium - WINTER PARK, FL

Leeward Way #C110, Winter Park, FL 32792

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

1 bed

1 bath

$1,400

Condo for rent

Bright & Inviting 1-Bedroom Condo with Charm

This spacious 1-bedroom, 1-bathroom condo spans 638 sq. ft. and boasts an inviting layout filled with natural light. Located on the first floor of Waterfall Cove, it offers convenient access to shops, restaurants, and parks. Enjoy the comfort of modern amenities including in-unit laundry, a dishwasher, and a walk-in closet. Perfect for embracing the vibrant Winter Park lifestyle!

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.

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

2.5 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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Updated: May 13, 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?

Winter Park's 2025 rental market shows one-bedroom apartments averaging around $1,400 per month, while two-bedroom units average around $1,700 monthly. Both apartment types experienced year-over-year decreases, with one-bedrooms declining 6.1% and two-bedrooms dropping 4.4% from 2024 levels.

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?

October stands out as the optimal month for apartment hunting in Winter Park, offering both the lowest seasonal rents and reduced competition among renters. The city sees an 8% difference between peak July pricing and October's off-peak rates, making fall timing particularly advantageous for budget-conscious searches.

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

Winter Park offers solid options for pet owners, with 48% of rental listings welcoming pets. This represents a substantial portion of the city's average 258 monthly apartment listings, providing pet owners with multiple housing choices across different property types.

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

Utilities are rarely included in Winter Park rental agreements, appearing in less than 1% of total listings. Among the limited options, one-bedroom apartments show the highest rate at 0.08% of listings, while studios currently show no utility-included options available.

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?

🔑Available apartment rentals230
💰Best rent deal3075 Aaron Burr Ave #C
Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos