2-Bedroom Homes for Rent in Winter Park, FL

• 

  

  

  /40

  $1,240 - $1,830 per month

  Seabrook

  1 - 2 Beds

  3114 Terry Brook Dr, Winter Park, FL 32792

  The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been

  3114 Terry Brook Dr, Winter Park, FL 32792
• 

  Explore Winter Park

• 

  

  

  /17

  $1,695 per month

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft
  • House for Rent

  2328 Inagua Way, Winter Park, FL 32792

  This 2 bedroom, 2 bathroom home is located in the Windward Square community near local Winter Park shops, restaurants, and schools. Features include a spacious floor plan with a large main living area, a lovely kitchen, dining room, a wonderful primary suite with walk-in closet, a laundry closet, a screened patio, a beautiful fenced backyard, and carport. Community amenities include 2 swimming

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  2328 Inagua Way, Winter Park, FL 32792
• 

  

  

  /37

  $1,318 - $3,121 per month

  Cranes Landing Apartments

  1 - 3 Beds

  3440 N Goldenrod Rd, Winter Park, FL 32792

  Incredible Move In Specials!Up to 6 Weeks Free!Receive a small kitchen appliance if you Look & Lease the same day!!!LIMITED TIME ONLY!!!Open House Saturday 10am - 4pm

  3440 N Goldenrod Rd, Winter Park, FL 32792
• 

  

  

  /22

  $2,000 per month

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Condo for Rent

  1500 Gay Rd Unit 9B, Winter Park, FL 32789

  Lakefront Community on beautiful Lake Killarney. Community Boat Ramp and Lakefront Deck. Community Heated Pool and Sauna. Walking distance to Grocery Store, Movie Theaters, Restaurants, Trader Joes. Close proximity to Park Avenue and Farmers Market. Peaceful Setting, Perfect Location! First Floor 2Bedroom/2Bath End Unit, beautifully renovated. New Kitchen with raised ceiling, new Cabinets,

  Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 9B, Winter Park, FL 32789
• 

  

  

  /23

  $1,881 - $6,506 per month

  Juno Winter Park

  Studio - 3 Beds

  1305 Morgan Stanley Ave, Winter Park, FL 32789

  Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

  1305 Morgan Stanley Ave, Winter Park, FL 32789
• 

  

  /12

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,038 Sq Ft
  • House for Rent

  1961 Casselwood St, Winter Park, FL 32792

  Welcome to your new home in vibrant Winter Park! This beautifully updated 2-bedroom, 2-bath condo features brand-new flooring, a private patio for relaxing mornings or evenings, and the convenience of an in-unit washer and dryer. With spacious bedrooms designed for comfort and privacy, this home perfectly blends style and functionality.Nestled in a highly desirable neighborhood, you’ll be

  Jacob Hara TRANSCEND REALTY

  1961 Casselwood St, Winter Park, FL 32792
• 

  

  /85

  $1,560 - $5,459 per month

  Berkshire Winter Park

  Studio - 3 Beds

  1874 Harmon Ave, Winter Park, FL 32789

  Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

  1874 Harmon Ave, Winter Park, FL 32789
• 

  

  /17

  $2,350 per month

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • House for Rent

  1919 Azalea Ave, Winter Park, FL 32792

  Super Home sits on a dead end street with LARGE LANDSCAPED YARD with Natural Landscaping. Enjoy long weekends on the large screened back patio. This TWO BEDROOM IS UPDATED and ready for the new tenant. Super Winter Park Area - Affordable living. Washer and Dryer in laundry area. Updated bathroom and kitchen. This one won't last long! Available immediately.

  Jane Slone CONWAY REALTY CORP

  1919 Azalea Ave, Winter Park, FL 32792
• 

  

  /74

  $1,500 - $4,336 per month

  Vintage Winter Park Apartments

  1 - 3 Beds

  7490 Dwell Well Way, Winter Park, FL 32792

  Dwell well with us. Welcome to quintessential Vintage Winter Park, a residential community featuring One, Two & Three bedroom apartments in Winter Park, FL. Spacious layouts and amenities welcome you home, along with exceptional service and an ideal location within walking distance to shopping, dining and entertainment options.

  7490 Dwell Well Way, Winter Park, FL 32792
• 

  

  /9

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,066 Sq Ft
  • Condo for Rent

  3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792

  Great rent . First flour . Two bedrooms' and two bathroom in great quite safe community. 3 miles from SAM Wearhouse.It is new pint and include washer and dryer. Its clean and ready to move in.

  Amin Abraham FLORIDA REALTY INVESTMENTS

  3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792
• 

  

  /43

  $1,639 - $3,252 per month

  Bainbridge Winter Park

  1 - 3 Beds

  1400 Morgan Stanley Ave, Winter Park, FL 32789

  Celebrate the power of possibilities. Signature details enhance grand features in expansive homes, all a promise to your heightened prosperity at Bainbridge Winter Park. In the heart of Winter Park, Florida’s lush parks and gardens, museums, festivals, and events - you’re central to the finer things in life.

  1400 Morgan Stanley Ave, Winter Park, FL 32789
• 

  

  /24

  $1,695 per month

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Condo for Rent

  851 Miles Ave Unit 21, Winter Park, FL 32789

  Enjoy a quiet but beautiful space at Aragon Condominiums. This first-floor corner unit allows for privacy with only one adjoining neighbor. It is a perfect place to call home with upgrades all around, including granite countertops, washer and dryer in unit, and a community pool just right outside your door. It is conveniently located in Winter Park, where you can enjoy many shops, restaurants,

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

  851 Miles Ave Unit 21, Winter Park, FL 32789
• 

  

  /20

  $1,529 - $2,599 per month

  Sapphire Winter Park

  1 - 3 Beds

  1743 Semoran Cir N, Winter Park, FL 32792

  Sapphire Winter Park offers the ultimate luxury oasis as a sanctuary of good living tucked away on 26-acres of lush landscaping. Located in the city of Winter Park, Florida, select apartments offer brand new washer & dryer, modern white shaker cabinets, quartz countertops, contemporary light & utility fixtures, stainless-steel appliances and vinyl wood floors in main areas with carpet in each

  1743 Semoran Cir N, Winter Park, FL 32792
• 

  

  /24

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 913 Sq Ft
  • Condo for Rent

  1250 S Denning Dr Unit 233, Winter Park, FL 32789

  Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a light and bright open floor plan, updated finishes, views of Mead Gardens, and one of Central Florida's most sought after locations! As you enter the front door, you are immediately welcomed by views of Mead Botanical Gardens, Khaki oak wood-look luxury vinyl floors, an open

  Samuel Kingsford STOCKWORTH REALTY GROUP

  1250 S Denning Dr Unit 233, Winter Park, FL 32789
• 

  

  /110

  $1,475 - $2,075 per month

  Oak Reserve at Winter Park

  1 - 3 Beds

  541 Oak Reserve Ln, Winter Park, FL 32792

  Welcome home to Oak Reserve at Winter Park Apartments, a quiet community where your needs and wishes are our priority. Covering all the bases for a comfortable living experience, our apartments in Winter Park, FL, are completed by lifestyle-oriented amenities, fantastic services, and a well-connected location within walking distance of Full Sail University. Short-term leases are available,

  541 Oak Reserve Ln, Winter Park, FL 32792
• 

  

  /37

  $2,599 per month

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Condo for Rent

  3254 Oak Lake Place Unit 137, Winter Park, FL 32792

  FURNISHED CORPORATE/EXECUTIVE RENTAL "THE FLORENCE" ,TOWNHOUSE COMMUNITY BOAST 2 BED/2.5 BATH EXECUTIVE CONDO IN THE HIDDEN OAKS COMMUNITY, WINTER PARK FLORIDA. THIS ELEGANT HOME FEATURES 1031 SQ. FT. OF LIVING SPACE, AND COMMUNITY POOL. 32'' AND 90" CABINETS IN THE SCANDINAVIAN DESIGNED KITCHEN. PORCELAIN TILE FLOORS IN THE KITCHEN AND BATHROOMS. FULLY EQUIPPED LAUNDRY ROOM FOR YOUR CONVENIENTLY

  Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP

  3254 Oak Lake Place Unit 137, Winter Park, FL 32792
• 

  

  /103

  $2,156 - $6,550 per month

  Paseo at Winter Park Village

  1 - 3 Beds

  940 W Canton Ave, Winter Park, FL 32789

  Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

  940 W Canton Ave, Winter Park, FL 32789
• 

  

  /18

  $1,680 per month

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft
  • Apartment for Rent

  2923 Antique Oaks Cir Unit GE, Winter Park, FL 32792

  Discover your new home! This beautiful 2-bedroom, 2-bathroom apartment offers the perfect balance between comfort and style. Ideal for families, couples, or professionals looking for a modern and functional space.?? Key Features:2 spacious bedrooms with closets2 modern, well-ventilated full bathroomsOpen-concept living and dining roomKitchen equipped with cabinets and a

  Michell Carrasquero GLOBALWIDE REALTY LLC

  2923 Antique Oaks Cir Unit GE, Winter Park, FL 32792
• 

  

  /50

  $1,497 - $2,018 per month

  Calibre Bend Apartments

  1 - 2 Beds

  3924 Calibre Bend Ln, Winter Park, FL 32792

  Calibre Bend Apartments offers a wide variety of apartment styles designed to accommodate the demands of today's sophisticated professional, while offering the setting and charm of yesteryear. You can expect unsurpassed amenities that will delight your senses, and a cozy community that makes coming home a breeze. Imagine your meals coming together perfectly in your gourmet kitchen, relaxing on

  3924 Calibre Bend Ln, Winter Park, FL 32792
• 

  

  /20

  $3,400 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Townhouse for Rent

  775 Maryland Ave, Winter Park, FL 32789

  Newly Remodeled!! This 2 bed 1 bath duplex in the heart of Winter Park is just a few short blocks from Rollins College and Park Avenue. Offering a brand new kitchen with stainless steel appliances and quartz counter top, a full size washer and dryer and new flooring throughout. There is one bed and bath downstairs and a spacious 2nd bedroom upstairs making the space very versatile for roommates

  Alexis Magargee ROAM FLORIDA REALTY LLC

  775 Maryland Ave, Winter Park, FL 32789
• 

  

  /40

  $1,391 - $2,447 per month

  The Taylor at Winter Park

  Studio - 3 Beds

  2000 Village Ln, Winter Park, FL 32792

  5 miles north of Orlando lies The Taylor at Winter Park. Experience true comfort and serenity in a newly renovated 1-, 2-, or 3-bedroom apartment. With spacious home layouts, sleek interior finishes, screened porches, private balconies, and stunning garden-style landscaping, you can enjoy a healthy, Zen lifestyle. Cut your commute and enjoy going out on the town with a prime location near

  2000 Village Ln, Winter Park, FL 32792
• 

  

  /23

  $1,695 per month

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft
  • House for Rent

  200 Saint Andrews Blvd Unit 3502, Winter Park, FL 32792

  This lovely 2 bedroom, 2 bathroom ground floor unit in the Four Seasons community is located in the heart of Winter Park. Enjoy all Downtown Winter Park has, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include vinyl plank flooring throughout, spacious

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  200 Saint Andrews Blvd Unit 3502, Winter Park, FL 32792
• 

  

  /36

  $1,366 - $2,854 per month

  Summerlin at Winter Park Apartments

  1 - 3 Beds

  3207 Rosebud Ln, Winter Park, FL 32792

  These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

  3207 Rosebud Ln, Winter Park, FL 32792
• 

  

  /25

  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 913 Sq Ft
  • Condo for Rent

  1250 S Denning Dr Unit 232, Winter Park, FL 32789

  Less than 1 mile from Rollins College and Park Ave in the highly desirable 32789 Winter Park zip code. This 2-Bedroom, 2-Bath hidden gem backs up to Mead Botanical Gardens. Also, less than 5 miles from from Downtown Orlando. This light-filled home features a brand-new kitchen with granite countertops & appliances, fresh paint, updated bathrooms, new carpet, and modern finishes throughout.

  Robert Isaac Rodriguez RE/MAX DOWNTOWN

  1250 S Denning Dr Unit 232, Winter Park, FL 32789
• 

  

  /26

  $1,195 - $1,965 per month

  Central Place At Winter Park

  1 - 3 Beds

  7000 University Blvd, Winter Park, FL 32792

  Central Place at Winter Park, where contemporary living meets convenience in a vibrant locale in Winter Park, FL. Our one, two, and three-bedroom apartment community offers a prime location on University Blvd. near Full Sail University and just moments away from the charming downtown Winter Park area. Experience the essence of modern living in our thoughtfully designed residences, featuring

  7000 University Blvd, Winter Park, FL 32792
• 

  

  /58

  $4,850 per month

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • Condo for Rent

  104 S Interlachen Ave Unit 114, Winter Park, FL 32789

  Welcome to the Cloisters, an exclusive lakefront condominium community in Winter Park, now available for lease. This first-floor two-bedroom, two-bath residence offers a thoughtfully updated open-concept layout and direct garden access. Entering from the main hallway, you step into a welcoming interior where the kitchen sits to the right, featuring a breakfast bar that connects seamlessly to the

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  104 S Interlachen Ave Unit 114, Winter Park, FL 32789
• 

  

  /50

  $1,200 - $1,715 per month

  Winter Park Woods

  Studio - 3 Beds

  7200 Aloma Ave, Winter Park, FL 32792

  This community boasts a prime location that effortlessly combines charm with convenience. Nestled in a well established neighborhood, it offers residents easy access to an array of amenities, including local shops, cafes, and restaurants, all just a short stroll away. The mature landscaping creates a tranquil atmosphere, inviting residents to take leisurely walks and enjoy the scenery.

  7200 Aloma Ave, Winter Park, FL 32792
• 

  

  /10

  $1,549 per month

  • 2 Beds
  • 1 Bath
  • 650 Sq Ft
  • Apartment for Rent

  1500 Michigan Ave Unit B, Winter Park, FL 32789

  This charming 2-bedroom, 1-bathroom apartment offers comfortable living space in a prime Winter Park location. Situated just around the corner from Orlando and Orange Avenues, residents enjoy easy access to downtown Orlando, Florida Hospital's main campus, I-4, and a variety of dining and entertainment options that make Winter Park one of the most desirable places to live. The home features a

  Steve Simpson 407 PROPERTIES

  1500 Michigan Ave Unit B, Winter Park, FL 32789
• 

  

  /44

  $1,257 - $3,558 per month

  Liv at Winter Park Apartment Homes

  Studio - 3 Beds

  4755 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to LIV at Winter Park, offering beautiful lakeside apartments for rent. Our Winter Park, Florida community offers your choice of studio, one-bedroom, two-bedroom, and three-bedroom apartment floor plans, with six distinct styles available. Experience the convenience of living just outside of the opportunities and excitement of Orlando, FL. Our spacious floor plans boast modern

  4755 N Goldenrod Rd, Winter Park, FL 32792
• 

  

  /19

  $1,895 per month

  • 2 Beds
  • 2.5 Baths
  • 1,133 Sq Ft
  • Townhouse for Rent

  200 Sandlewood Trail Unit 4, Winter Park, FL 32789

  ovely, light and airy home with newer appliances, fresh paint through out and newer laminate flooring upstairs. The kitchen shines with natural light and eat-in space, large window that floods the room with natural light. The spacious living and dining features a corner fireplace - tile flooring and over-sized sliders that open to back patio and greens space...pool is short walk across the yard.

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  200 Sandlewood Trail Unit 4, Winter Park, FL 32789
• 

  

  /50

  $1,630 - $3,123 per month

  Seven41 Winter Park

  Studio - 2 Beds

  741 Clay St, Winter Park, FL 32789

  Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

  741 Clay St, Winter Park, FL 32789
• 

  

  /17

  $2,500 per month

  • 2 Beds
  • 2.5 Baths
  • 1,204 Sq Ft
  • Townhouse for Rent

  645 Huntington Ave Unit 7, Winter Park, FL 32789

  Live in style in this renovated 2-bedroom, 2.5-bath townhome located in the heart of Winter Park. The modern kitchen features stainless steel appliances, granite counters, and upscale finishes. Both bedrooms have private balconies, and the master includes a versatile loft space, great for a workspace or lounge. The home also comes equipped with a front-load washer and dryer. Outside, enjoy a

  Summer Hornburg BELMONT REALTY

  645 Huntington Ave Unit 7, Winter Park, FL 32789
• 

  

  /39

  $903 - $1,535 per month

  San Jose Apartments

  1 - 3 Beds

  2353 Winter Woods Blvd, Winter Park, FL 32792

  Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

  2353 Winter Woods Blvd, Winter Park, FL 32792
• 

  

  /26

  $2,400 per month

  • 2 Beds
  • 2.5 Baths
  • 1,495 Sq Ft
  • Condo for Rent

  2340 Sun Valley Cir Unit 2340, Winter Park, FL 32792

  Welcome to 2340 Sun Valley Circle, Winter Park, FL 32792, a stylish 2-bedroom, 2-bath condo featuring a bonus loft that’s perfect for a office or guest space. Step into an updated layout boasting vaulted ceilings, modern luxury flooring, a remodeled kitchen, and a sleek, refreshed bathroom that feels both contemporary and timeless. In-unit laundry, two dedicated parking spaces, and smart,

  Melissa Johnson EXP REALTY LLC

  2340 Sun Valley Cir Unit 2340, Winter Park, FL 32792
• 

  

  /50

  $1,150 - $2,848 per month

  Sovereignty at Winter Park Apartments

  1 - 2 Beds

  7745 Brandywood Cir, Winter Park, FL 32792

  We offer 1 and 2 bedroom apartment homes with fully equipped kitchens, garden tubs, vaulted ceilings, ornamental chair rails, and so much more. Our community has a designer clubhouse, state-of-the-art fitness center, a sparkling pool, planned social activities, a high-speed internet business center, and 24 hour emergency maintenance. Winter Park location convenient to Full Sail, UCF, Valencia,

  7745 Brandywood Cir, Winter Park, FL 32792
• 

  

  /15

  $1,850 per month

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft
  • Condo for Rent

  1250 S Denning Dr Unit 105, Winter Park, FL 32789

  Welcome to your dream home in the heart of Winter Park! This beautifully updated 2-bedroom, 2-bath condo offers the perfect blend of style, comfort, and convenience. Just steps away from Mead Gardens, fantastic restaurants, cozy coffee shops, vibrant cocktail bars, and so much more, you’ll love the walkable and bikeable lifestyle. Park Avenue is only minutes away, making it easy to enjoy

  Joe Devlin DEVLIN INVESTORS & ASSOCIATES

  1250 S Denning Dr Unit 105, Winter Park, FL 32789
• 

  

  /16

  $1,135 - $1,975 per month

  Sorrento

  Studio - 3 Beds

  2400 Howell Branch Rd, Winter Park, FL 32792

  2400 Howell Branch Rd, Winter Park, FL 32792
• 

  

  /15

  $2,050 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Apartment for Rent

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

  Lakefront Living at Its Best: Renovated 1st Floor End Unit on Lake KillarneyExperience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney.Key Features:Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings.Water Activities: Benefit from

  Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

  1500 Gay Rd Unit 3B, Winter Park, FL 32789
• 

  

  /29

  $1,166 - $2,139 per month

  Atlas at Winter Park

  1 - 3 Beds

  3733 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to Atlas at Winter Park!

  3733 N Goldenrod Rd, Winter Park, FL 32792
• 

  

  /16

  $3,000 per month

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft
  • House for Rent

  430 Ololu Dr, Winter Park, FL 32789

  Interested in trying out the lake life in Winter Park? 430 Ololu is available FOR RENT beginning October 1st on Lake Killarney! This 2 bedroom, 1 bath home has a brand new metal roof, a newly renovated kitchen with new appliances, a newer washer and dryer, and a DREAM backyard with views of and private access to Lake Killarney. Bring your kayak, jet ski, boat, or even a seaplane and make your way

  Ellen Hencken MILLER GRANT AND COMPANY

  430 Ololu Dr, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 3