Zumper

Apartments for Rent in Winter Park, FL

275 rentals

151 N Orlando Ave #101 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

151 N Orlando Ave #101, Winter Park, FL 32789

In-unit laundry | Swimming pool | Dishwasher

2 beds

1 bath

$1,799

Condo for rent

Chic Lakeside Condo with Modern Finishes

This stylish 2-bedroom, 1-bath condo blends comfort and charm in a prime lakeside location. Featuring an open layout, modern kitchen with granite countertops, and energy-efficient sliding doors, this home offers effortless living. Enjoy stunning sunsets from the lakefront pool, picnic area, and access to a private boat ramp. Just minutes from Winter Park Village and right next to Trader Joe’s, this condo embodies the perfect balance of relaxation and convenience.

295 Sandlewood Trl - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

2 BR / 2.5 BA Townhome In Sandlewood Creek

295 Sandlewood Trl, Winter Park, FL 32789

On-site laundry | Outdoor space

2 beds

2.5 baths

$1,895

House for rent

Modern Townhome with Chic Features & Community Pool

This inviting 2-bedroom, 2.5-bath townhouse in the desirable Sandlewood Creek community offers a bright open living area, a stylish kitchen with quartz countertops, and a lovely primary suite. Enjoy outdoor relaxation on the private rear patio, and take advantage of community amenities like the pool. With easy access to Winter Park's shops, dining, and entertainment options, this home is perfect for those seeking modern living in a vibrant area.

520 N Orlando Ave #125 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

In-unit laundry | Fitness center | Storage

1 bed

1 bath

$1,710

Apartment for rent

Available May 7

Chic Urban Loft with Unique Two-Level Layout

Experience vibrant urban living in this stylish two-level loft featuring high ceilings, oversized windows, and industrial charm. Enjoy amenities like a fitness center, private parking, and bike storage. Located steps from dining and entertainment options, this pet-friendly 1-bed, 1-bath, 690 sq. ft. apartment offers the perfect blend of comfort and convenience in Winter Park. Pre-lease now for $500 off and a low security deposit!

5334 Lake Howell Rd - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

5334 Lake Howell Rd, Winter Park, FL 32792

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

3 beds

2 baths

$2,850

Apartment for rent

Available Jun 1

Bright & Spacious Fully Renovated 3-Bed Apartment

Experience modern living in this fully renovated 3-bedroom, 2-bath apartment, featuring a spacious floor plan with tile throughout. The bright, open living area is designed for entertaining, and the large front and backyards provide ample outdoor space. Perfectly located just minutes from Winter Park’s shops and restaurants, this home is an ideal choice for those seeking comfort and convenience. Move-in ready starting June 1st!

1313 Buckingham Rd - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

1313 Buckingham Rd, Winter Park, FL 32789

In-unit laundry | On-site management | Outdoor space

4 beds

2 baths

$3,800

Apartment for rent

Available Jun 1

Charming 4-Bed Home with Sunroom & Fenced Yard

This delightful 4-bedroom, 2-bath apartment features beautiful hardwood floors throughout, creating a warm atmosphere. Enjoy sunny days in the sunroom or unwind in the spacious fenced yard. Ideally located just minutes from shops, restaurants, and Rollins College, this pet-friendly home offers a perfect blend of comfort and convenience. In-unit laundry and lawn service are also included, making this move-in ready home an ideal choice for students and families alike.

644 N Knowles Ave #8 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

644 N Knowles Ave #8, Winter Park, FL 32789

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

3 beds

2 baths

$2,850

Apartment for rent

Available Jun 1

Modern Winter Park Condo with Scenic Views

Enjoy the vibrant lifestyle in this beautifully renovated 3-bedroom, 2-bathroom apartment, featuring modern upgrades and stunning views of the Winter Park 9 golf course from the balcony. The open floor plan showcases sleek solid surface flooring and a designer kitchen equipped with stainless steel appliances. Located just steps from Rollins College and Park Avenue's shops and cafes, this move-in-ready retreat is perfect for those seeking convenience and charm in Downtown 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!

1580 Oakhurst Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1580 Oakhurst Ave, Winter Park, FL 32789

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

4 beds

2.5 baths

$4,700

$4,495

Price drop

House for rent

Charming Two-Story Home with Outdoor Oasis

This stunning 4-bedroom, 2.5-bath residence features recent updates and a stylish interior, including hardwood floors and granite countertops. The gourmet kitchen flows into a cozy family room with a wood-burning fireplace. A spacious master suite offers a luxurious bath and access to a delightful second-floor deck. Enjoy the serene front porch and lush backyard with fruit trees. Ideally situated near shops, restaurants, and top schools, this home is perfect for Florida living.

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717 Denton Rd - Photo 1 of 1

5d+ ago

House for rent in Winter Park

717 Denton Rd, Winter Park, FL 32792

On-site management | Package service | Business center

4 beds

2 baths

$2,099

House for rent

Available May 19

Cozy Family Home with Spacious Bonus Room

This charming 4-bedroom, 2-bath home offers 1,411 sq ft of comfortable living space, complete with a bonus room ideal for an office or play area. The eat-in kitchen comes with stainless steel appliances, perfect for family meals. Enjoy the convenience of a 2-car carport and proximity to major roads, shopping, and Full Sail University. Pet-friendly with a spacious yard, make this Winter Park residence a perfect family retreat!

3027 Patel Dr #NA - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

$1,800 - 2 Bedroom 2 Bathroom House In Winter Park With Great Amenities

3027 Patel Dr #NA, Winter Park, FL 32792

In-unit laundry | Air conditioning | Assigned parking

2 beds

2 baths

$1,800

Apartment for rent

Available Mar 12

Charming 2-Bed House with Backyard and Parking

Experience the best of both worlds in this cozy 2-bedroom, 2-bath house featuring an inviting open floor kitchen. Enjoy the private outdoor space with citrus trees, perfect for grilling and relaxation. Conveniently located between UCF and Full Sail, this home boasts ample parking for up to 4 cars. Your furry friends are welcome with proper care. Easy access to shopping and restaurants, this property marries comfort and convenience beautifully.

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.

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1860 Via Contessa - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1860 Via Contessa, Winter Park, FL 32789

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

8 beds

6 baths

$13,500

House for rent

Luxe 7,000 SF Dream Home with Private In-Law Suite

This extraordinary residence features 8 bedrooms and 6 bathrooms across three levels, offering an exceptional blend of sophistication and livability. The chef's kitchen and expansive primary suites are just the beginning. Entertain seamlessly between the spacious family room and covered patio, while a fully-equipped in-law suite downstairs promises flexibility. Located in a prestigious neighborhood, it's the perfect retreat for modern living.

1611 Little Wren Ln - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

3 BR / 2.5 BA Townhouse In Hawks Crest

1611 Little Wren Ln, Winter Park, FL 32792

In-unit laundry | Walk-in closets | Carpet

3 beds

2.5 baths

$2,730

House for rent

Available Mar 12

Modern Townhouse with Pool & Serene Backyard Oasis

Embrace contemporary living in this stylish 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 countertops, and stainless steel appliances. The primary suite offers a walk-in closet and elegant bath. Enjoy outdoor relaxation in the private backyard patio, plus community amenities like a pool, cabana, park, and playground. Convenient access to Winter Park dining and shopping.

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.

252 Balfour Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

House for rent

Modern Townhome with Serene Green View Retreat

This remodeled 3-bedroom, 2.5-bath townhouse offers modern comforts with an updated kitchen and bathrooms. Enjoy the enclosed/screen patio overlooking a tranquil green view and courtyard. Additional perks include a solar boosted water heater and a pet-friendly environment, perfect for dog lovers. With 1,727 sq ft of living space, this townhome blends convenience and style, making it an ideal retreat in Winter Park.

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

1.5 baths

$2,435

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!

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

Elegant Oasis with Pool in Prime Location

Fully renovated 4-bedroom, 3-bath home offers 2,207 SF of sunlit living space just steps from Winter Park Racquet Club. The private backyard features a sparkling pool and heated spa, surrounded by lush landscaping for perfect outdoor relaxation. Enjoy modern comforts with a new roof, dual-speed AC, and included services for gardening and pool maintenance. This dreamy retreat combines luxury with low utility costs, making it an ideal choice for effortless Florida living.

933 Early Ave #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Cozy Midcentury Modern Home with Easy Highway Access

933 Early Ave #NA, Winter Park, FL 32789

In-unit laundry | Air conditioning | Garage parking

3 beds

1.5 baths

$2,325

House for rent

Available Mar 9

Charming Midcentury Retreat with Spacious Yard

This fully furnished 3-bedroom, 1.5-bath midcentury modern home boasts refinished parquet hardwood floors and an abundance of natural light. Enjoy open living areas, two Florida rooms, and a fenced backyard. Additional features include a one-car garage and a large driveway. Located just minutes from I-4, this stylish retreat offers easy access to premier shopping and dining in the vibrant Winter Park area, making it an ideal rental escape.

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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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

$2,200

Price drop

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.

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 | On-site laundry

3 beds

2.5 baths

$3,850

House for rent

Elegant Home with Gourmet Kitchen & Patio Retreat

This stunning 3-bedroom, 2.5-bath residence showcases elegance and comfort in 1,880 sq ft. The gourmet kitchen boasts wood cabinetry, stainless steel appliances, and granite countertops, perfect for culinary enthusiasts. French doors lead to a large, secluded patio, ideal for entertaining. The spacious master suite features an ensuite with dual vanities and a jacuzzi. Conveniently located near Park Avenue and Rollins College, this pet-friendly home is a true delight.

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

$5,500

$4,000

Price drop

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.

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.

307 Sandlewood Trl - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

2 BR / 2.5 BA Townhome In Sandlewood Creek

307 Sandlewood Trl, Winter Park, FL 32789

On-site laundry | Outdoor space

2 beds

2.5 baths

$1,895

House for rent

Available May 29

Modern Townhome with Pool in Vibrant Community

Embrace a stylish lifestyle in this pet-friendly 2-bedroom, 2.5-bathroom townhome featuring 960 sq ft of living space. Enjoy a spacious main area with open living and dining, a chic kitchen with quartz countertops, and a lovely primary suite with custom finishes. A rear patio offers outdoor relaxation, while the community pool adds a touch of fun. Located near Park Avenue's shops, dining, and recreational amenities, this home is perfect for those seeking convenience in Winter Park.

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.

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

2.5 baths

$2,500

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!

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2743 Sanbina St - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

2743 Sanbina St, Winter Park, FL 32789

In-unit laundry | Concierge service | On-site management

3 beds

2 baths

$2,500

Apartment for rent

Available Feb 27

Bright & Charming 3-Bed Oasis with Modern Upgrades

This beautifully updated 3-bedroom, 2-bath home features classic terrazzo flooring and a recently remodeled kitchen with brand-new appliances. The primary suite offers a spacious walk-in closet and ensuite bath. Enjoy a fully fenced backyard, 2-car parking, and included washer/dryer. Nestled in prime Winter Park, this inviting residence is close to shopping, dining, and parks, offering a blend of modern comforts and timeless charm.

715 Warrenton Rd - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

715 Warrenton Rd, Winter Park, FL 32792

In-unit laundry | Dishwasher | Microwave

3 beds

2 baths

$2,195

Condo for rent

Charming 3-Bed Condo with Bright Open Spaces

This beautifully maintained 3-bedroom, 2-bath condo offers a spacious layout teeming with natural light. The efficient kitchen boasts ample storage, perfect for meal preparations. The primary suite features an en-suite bath and generous closet space, while additional bedrooms provide versatility. Enjoy a large yard ideal for gatherings or relaxing evenings. Conveniently located near shopping, dining, and top-rated schools, this residence offers comfort and accessibility in Winter Park.

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!

1000 S Semoran Blvd #115 - Photo 1 of 1

5d+ ago

Golfside condo for rent in Winter Park

2 Bedroom | 2 Bathroom Condo

1000 S Semoran Blvd #115, Winter Park, FL 32792

Air conditioning | On-site laundry | Assigned parking

2 beds

2 baths

$1,400

Condo for rent

Available Feb 26

Bright & Spacious Condo with Pool Access

This charming 2-bedroom, 2-bathroom condo offers over 1,000 sq ft of comfortable living space, featuring an open floor plan and a screened-in patio. Located in the Golfside Villas community, enjoy easy access to Downtown Orlando, shopping, and dining. Residents benefit from a community pool, laundry facilities, and assigned parking. Ideal for those seeking a pet-friendly home in a vibrant neighborhood!

7429 Daniel Webster Dr #14E - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease!

7429 Daniel Webster Dr #14E, Winter Park, FL 32792

In-unit laundry | Furnished | Package service

2 beds

2 baths

$1,740

Condo for rent

Fully Furnished 2-Bed Condo with Rent Credit!

Embrace comfortable living in this charming 2-bedroom, 2-bathroom condo, featuring fresh paint, upgraded lighting, and spacious bedrooms. Enjoy a stylish kitchen with new granite countertops and in-unit laundry. Perfectly located for easy access to Disney, Cocoa Beach, and major colleges. Take advantage of a special rent credit and resident benefits package. This beautifully maintained unit offers both convenience and comfort—just unpack and enjoy!

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

$1,400

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!

421 W Fairbanks Ave - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

Apartment - WINTER PARK, FL

421 W Fairbanks Ave, Winter Park, FL 32789

In-unit laundry | Hardwood floor | Ceiling fan

3 beds

3 baths

$3,750

Apartment for rent

Stunning 1925 Loft with Designer Touches

Experience luxury living in this fully reimagined 3-bedroom, 3-bathroom loft, occupying the entire second floor of a historic brick building. With high ceilings and abundant natural light from skylights, the open concept space features hardwood flooring and sleek quartz countertops. Each bedroom offers a private ensuite bath, ensuring both comfort and privacy. Located just two blocks from Park Avenue, this designer residence combines historic charm with modern elegance, steps away from local shopping and dining.

520 N Orlando Ave #119 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Park

In-unit laundry | Fitness center | Elevator

1 bed

1 bath

$1,825

Apartment for rent

Available Apr 10

Stylish Loft Living in the Heart of Winter Park

Experience the vibrant lifestyle of Winter Park in this unique 1-bed, 1-bath loft featuring an impressive two-level layout with high ceilings and oversized windows. Enjoy the convenience of a fitness center, private parking, and an indoor patio, all steps away from delicious dining and shopping at Winter Park Village. Perfect for those seeking modern living in a bustling community, this pet-friendly apartment combines style and comfort seamlessly.

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612 Montego Bay Ct #612 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condominium - WINTER PARK, FL

612 Montego Bay Ct #612, Winter Park, FL 32792

In-unit laundry | Ceiling fan | Fireplace

2 beds

2 baths

$1,850

Condo for rent

Charming Villa with Fireplace and Private Patio

This cozy one-story villa features 2 bedrooms and 2 full baths, offering a bright living-dining area complete with a charming fireplace. Enjoy outdoor living on the private patio, and convenience with an included washer and dryer. Located in desirable Winter Park, this home is near shopping, major highways, and local colleges, making it an ideal spot for modern living. Pets are welcome with some restrictions.

612 Trinidad Ct #612 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Park

Condominium - WINTER PARK, FL

612 Trinidad Ct #612, Winter Park, FL 32792

In-unit laundry | Swimming pool | Fitness center

2 beds

2 baths

$1,850

Condo for rent

Bright & Cozy Condo with Private Outdoor Space

This charming 2-bed, 2-bath condo villa offers a spacious 1,037 sq ft of living space, featuring renovated kitchen and bathrooms, ceramic tile flooring, and a cozy fireplace. Enjoy the natural light from abundant windows, the convenience of in-unit laundry, and large walk-in closets. Step outside to the covered patio or explore the small courtyard. Residents benefit from nearby community amenities, including a pool and fitness center, all in a pet-friendly setting!

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.

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.

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!

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!

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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

5.5 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.

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.

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

$2,200

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!

7350 Swallow Run #1 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

7350 Swallow Run, Winter Park, FL 32792 - 1

7350 Swallow Run #1, Winter Park, FL 32792

Swimming pool

2 beds

2 baths

$1,650

House for rent

Available Jul 1

Stylish Ground-Floor Townhouse with Pool Access

This spacious 2-bedroom, 2-bathroom ground-floor townhouse features freshly painted interiors, modern appliances, and sleek tile flooring throughout. Enjoy granite countertops in the kitchen and relax by the community pool. Conveniently located near Full Sail University, UCF, and various shopping and dining options just minutes away. A perfect blend of comfort and accessibility awaits!

2619 Ambergate Rd - Photo 1 of 1

5d+ ago

House for rent in Winter Park

2619 Ambergate Rd, Winter Park, FL 32792

Garage parking | Fireplace | Outdoor space

3 beds

1.5 baths

$2,350

House for rent

Charming Home with Bonus Room and Fenced Yard

Experience the vibrancy of Winter Park in this charming 3-bedroom residence featuring a bonus room perfect for a home office. Enjoy peace of mind with a fenced backyard, a cozy fireplace, and the benefits of solar panels. Conveniently located near fine dining, entertainment, and top-rated schools, this home is within minutes of rolling’s College and UCF. With 1,598 sq ft of living space, your new chapter in this inviting community awaits!

5d+ ago

8.8

Very good

Winter Park Woods

115 Winter Way, Winter Park, FL 32792

Air conditioning | On-site laundry | Balcony

Studio–3 beds

1–2 baths

$1,185–$1,715

Apartment for rent

Top amenities
On-Site Laundry
Swimming Pool
Showing 51 - 100 of 100 results
Home > Apartments in Winter Park
Updated: March 28, 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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