Winter Park, FL Houses for Rent

• 

  

  

  /53

  $9,700 Per Month

  • 4 Beds
  • 5.5 Baths
  • 4,392 Sq Ft
  • House for Rent

  1760 Legion Dr, Winter Park, FL 32789

  Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect

  Steven Looper CHARLES RUTENBERG REALTY ORLANDO

  1760 Legion Dr, Winter Park, FL 32789
• 

  

  

  /12

  $1,900 Per Month

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft
  • Gorgeous, Completely Remodeled 2/2.5 Condo in Sandlewood Creek- Winter Park!

  303 Sandlewood Trail, Winter Park, FL 32789

  Welcome home to this beautifully renovated two-story condo in desirable Sandlewood Trails. This 2-Bedroom, 2.5 Bath condo home is ideally located in Winter Park and is one of the few condo communities where residents are close enough to bike or walk to Dommerich Elementary and Maitland Middle School.As you enter, you are welcomed by a spacious Great Room and attractive gray-toned laminate

  303 Sandlewood Trail, Winter Park, FL 32789
• 

  

  

  /23

  $3,500 Per Month

  • 4 Beds
  • 2 Baths
  • 2,099 Sq Ft
  • House for Rent

  2115 Sycamore Dr, Winter Park, FL 32789

  Updated Charming 4 Bed/2 Bath mid-century home located in Northwood Terrace/Audubon Park (just across the street from Baldwin Park). You will love the large lot .34 Acres with it botanical garden, meditation area, a patio with a raised HOT Tub (perfect for a starry night) and plenty of privacy with all the lush foliage. The front door opens to a great room where the kitchen, living area, dining

  John Goggin STOCKWORTH REALTY GROUP

  2115 Sycamore Dr, Winter Park, FL 32789
• 

  

  

  /20

  $3,995 Per Month

  • 3 Beds
  • 3 Baths
  • 1,715 Sq Ft
  • House for Rent

  1667 Mizell Ave, Winter Park, FL 32789

  Minimum Deposit $3995. Monthly Rent $3995. Available June 1st!Contact Polina at or email to schedule your private showing. Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been established.Welcome to your dream Winter Park home! This charming 3-bedroom, 3 full bathroom gem is the epitome of comfort and

  1667 Mizell Ave, Winter Park, FL 32789
• 

  

  

  /89

  $4,000 Per Month

  • 4 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • House for Rent

  1815 Barker Dr, Winter Park, FL 32789

  Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals, airports, Winter Park's cultural gems,

  Benjamin Cole, IV SOTERA LIVING

  1815 Barker Dr, Winter Park, FL 32789
• 

  

  /15

  $2,095 Per Month

  • 3 Beds
  • 2 Baths
  • 1,324 Sq Ft
  • House for Rent

  704 Carnation Dr, Winter Park, FL 32792

  Welcome to 704 Carnation Drive in Winter Park! This amazing home is located on a quiet street in the Eastbrook subdivision off Aloma Ave and was just freshly painted inside and out. The single-story home features an open concept living room/dining room/kitchen floorplan with stainless steel appliances, granite countertops, ceiling fan and ceramic tile flooring throughout. There is plenty of

  704 Carnation Dr, Winter Park, FL 32792
• 

  

  /32

  $3,475 Per Month

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft
  • House for Rent

  1850 Whitehall Dr, Winter Park, FL 32789

  This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1850 Whitehall Dr, Winter Park, FL 32789
• 

  

  /9

  $2,100 Per Month

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Nice 3 bedroom, 2 bath single family home

  3036 Patel Dr, Winter Park, FL 32792

  Available May 1st! 3/2 with open-concept kitchen. Your new home has an open and airy living room/kitchen area with easy-to-maintain tile. A HUGE screened patio looks out to a private wooded backyard. Privacy fence and attached one-car garage make this the perfect place to call home! The home is nestled on a cul-de-sac minutes from Full Sail.All ERA Grizzard Real Estate residents are

  3036 Patel Dr, Winter Park, FL 32792
• 

  

  /18

  $4,300 Per Month

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • House for Rent

  1026 S Lakemont Ave, Winter Park, FL 32792

  Lawn and pool maintenance included in rent! Welcome to this beautifully upgraded Winter Park pool home, designed for effortless living and exceptional entertaining. This 3-bedroom, 2-bath residence offers an open, inviting floor plan with a spacious kitchen featuring updated countertops and cabinetry, stainless steel appliances, beautiful bathroom finishes and updated flooring throughout. The

  Lianna D'Angelo SOTERA LIVING

  1026 S Lakemont Ave, Winter Park, FL 32792
• 

  

  /21

  $1,200 Per Month

  • 1 Bed
  • 1 Bath
  • 537 Sq Ft
  • One bedroom apt 7 or 12 months furnish or unfurnished. Apartamento disponible amueblado o sin mue...

  3075 Aaron Burr Ave, Winter Park, FL 32792

  Centrally located in Winter Park near Full Sail University, and check out this cute move-in ready, 1 Bed/1 Bath second-floor condo with a rear balcony. All tiled flooring, new paint, new toilets and light fixtures, new dishwasher and range. The community features a large swimming pool and a coined laundry room inside a community multipurpose room. This location is zoned for A-rated schools and

  3075 Aaron Burr Ave, Winter Park, FL 32792
• 

  

  /43

  $19,000 Per Month

  • 5 Beds
  • 5.5 Baths
  • 5,164 Sq Ft
  • House for Rent

  1221 Richmond Rd, Winter Park, FL 32789

  Owner/Builder/Agent - An Award-Winning Architectural Masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Welcome to 1221 Richmond Rd, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of Winter Park-offering deeded lake access to the Winter Park Chain of Lakes. This architectural showpiece was honored as the 2024

  Christopher Salhab La Rosa Realty Llc

  1221 Richmond Rd, Winter Park, FL 32789
• 

  

  /6

  $1,540 Per Month

  • 3 Beds
  • 1.5 Baths
  • House for Rent

  105 Jergo Rd, Winter Park, FL 32792

  This unique 3 bedroom, 1.5 bathroom Duplex is ready to welcome its new occupants. Spread over one story, this residence offers a perfect blend of space, comfort, and modern amenities. Enjoy ample space for your family with generously sized living areas, including a wide living room for gatherings and quality family time. The Kitchen is equipped with all the essential appliances you would need.

  105 Jergo Rd, Winter Park, FL 32792
• 

  

  /78

  $10,000 Per Month

  • 5 Beds
  • 4 Baths
  • 4,200 Sq Ft
  • House for Rent

  1814 Barker Dr, Winter Park, FL 32789

  Stunning newer-construction luxury home in Winter Park offering 5 bedrooms, 4 baths, and 4,100 sq ft of modern living. Sleek architectural lines, abundant natural light, and seamless indoor–outdoor flow define this exceptional residence. The chef’s kitchen features premium stainless steel appliances, breakfast bar, custom cabinetry, and a large walk-in pantry. The spacious living area includes a

  Tab Bish LLC REAL BROKER, LLC

  1814 Barker Dr, Winter Park, FL 32789
• 

  

  /11

  $1,950 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,024 Sq Ft
  • House for Rent

  731 W Comstock Ave, Winter Park, FL 32789

  Close to downtown Winter Park, Winter Park Village, and Park Avenue - Charming 3 bedroom 1.5 bath home, with single carport, fenced backyard, ceiling fans and blinds. Tile floors in main living areas and NEW carpet in bedrooms. Additional sun room located off the kitchen with entry to/from carport. This home is available for immediate move in. PETS NEGOTIABLE. Please call to schedule an

  731 W Comstock Ave, Winter Park, FL 32789
• 

  

  /22

  $3,950 Per Month

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft
  • House for Rent

  425 Balmoral Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. NOW AVAILABLE FOR LEASE IN ONE OF WINTER PARK’S MOST DESIRABLE ZIP CODES! Welcome to 425 Balmoral Road, a beautifully updated 3 BEDROOM, 2 BATHROOM home situated on a spacious CORNER LOT in the heart of 32789. Offering approximately 1,929 SF of living space, this charming residence is located near the highly sought after Windsong area, surrounded by

  Nydia Marrero ZEN LIVING HOMES LLC

  425 Balmoral Rd, Winter Park, FL 32789
• 

  

  /5

  $1,950 Per Month

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft
  • House for Rent

  4800 Tangerine Ave, Winter Park, FL 32792

  Beautiful & Spacious 2-Bedroom, 2-Bath Condo for Rent in Winter Park – $1,950/MonthDiscover the perfect blend of comfort, convenience, and lifestyle in this beautifully maintained condo located in the highly desirable Winter Park area. This home offers an exceptional layout with 2 spacious bedrooms and 2 full bathrooms, ideal for families, professionals, or roommates seeking a comfortable and

  4800 Tangerine Ave, Winter Park, FL 32792
• 

  

  /30

  $2,100 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,279 Sq Ft
  • House for Rent

  2846 Euston Rd, Winter Park, FL 32789

  Special of the month! $2100 for the first 2 months then $2350. Welcome to a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes from I4, close to Park Avenue District, College Park, major shopping centers and

  Vanessa Laboy 365 REALTY, INC.

  2846 Euston Rd, Winter Park, FL 32789
• 

  

  /15

  $1,740 Per Month

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft
  • Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease!

  7429 Daniel Webster Dr, Winter Park, FL 32792

  Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease! Welcome to this enchanting fully furnished 2-bedroom, 2-bathroom condo nestled in the heart of Winter Park, FL! Offering easy access to a plethora of attractions, this home invites you to immerse yourself in the magic of Disney, just 30 minutes away, or bask in the sun at picturesque Cocoa Beach, all

  7429 Daniel Webster Dr, Winter Park, FL 32792
• 

  

  /21

  $2,649 Per Month

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft
  • House for Rent

  1947 Summerfield Rd, Winter Park, FL 32792

  Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act

  Steve Simpson 407 PROPERTIES

  1947 Summerfield Rd, Winter Park, FL 32792
• 

  

  /13

  $2,550 Per Month

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • **MOVE IN SPECIAL $500 off first months rent** Beautiful 2 bedroom, 2 bath Condo located in Winte...

  110 Killarney Bay Ct, Winter Park, FL 32789

  **MOVE IN SPECIAL $500 off first months rent** Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining.Both bedrooms

  110 Killarney Bay Ct, Winter Park, FL 32789
• 

  

  /39

  $12,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,064 Sq Ft
  • House for Rent

  1041 Tuscany Place, Winter Park, FL 32789

  Nestled along a quiet brick-lined street in Winter Park’s coveted Via’s neighborhood, 1041 Tuscany Place offers a rare blend of elegance, comfort, and breathtaking natural beauty. From nearly every room, this exceptional residence captures tranquil views of the private backyard and picturesque Lake Temple beyond. Inside, a thoughtfully designed open floor plan is enhanced by soaring vaulted

  Brad Barnett COMPASS FLORIDA LLC

  1041 Tuscany Place, Winter Park, FL 32789
• 

  

  /37

  $2,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Affordable 3BR Home in Winter Park – Prime Location & Move-In Ready!

  151 N Orlando Ave, Winter Park, FL 32789

  Discover this affordable and well-located 3-bedroom, 2-bathroom home in the desirable Winter Park area, perfect for those seeking comfort, convenience, and long-term stability.This property offers a functional layout with comfortable living spaces, ideal for families or individuals looking for a practical and welcoming place to call home.

  151 N Orlando Ave, Winter Park, FL 32789
• 

  

  /29

  $2,650 Per Month

  • 4 Beds
  • 2 Baths
  • 2,053 Sq Ft
  • House for Rent

  7619 Georgeann St, Winter Park, FL 32792

  Welcome to 7619 Georgeann Street, a beautifully appointed 2,053+ sq. ft. single-family home that captures the essence of modern living in one of Winter Park’s most desirable neighborhoods. Thoughtfully designed and meticulously maintained, this residence offers the perfect blend of sophistication, comfort, and everyday functionality. Step through the front door and instantly feel the openness

  Ting Li SOUTH EARTH REALTY LLC

  7619 Georgeann St, Winter Park, FL 32792
• 

  

  /7

  $1,600 Per Month

  • 2 Beds
  • 2 Baths
  • 967 Sq Ft
  • 1/2 Duplex in Winter Park

  3012 Patel Dr, Winter Park, FL 32792

  Nice two bedroom, two bath home with spacious kitchen and living area. House is tiled throughout. Driveway accommodates 2 cars. Fenced in backyard with small shed. Close to Target, Costco Publix, Aldi. Winter Park Schools.

  3012 Patel Dr, Winter Park, FL 32792
• 

  

  /15

  $2,095 Per Month

  • 3 Beds
  • 2 Baths
  • 1,613 Sq Ft
  • House for Rent

  1724 Peruvian Ln, Winter Park, FL 32792

  Live in this updated home in Winter Park with 3 bedroom, 2 bathrooms. Large formal living area and a separate family room with dining. Kitchen with Stainless Steel appliances, Granite counter tops throughout, Ceramic Tile and Carpet flooring. Freshly painted interior and exterior. Large, fenced backyard. Laundry-room with Washer/Dryer hookups. *Bonus Amenity Included* - All residents are enrolled

  Mo Jabr RE/MAX 200 REALTY

  1724 Peruvian Ln, Winter Park, FL 32792
• 

  

  /19

  $1,299 Per Month

  • 1 Bed
  • 1 Bath
  • 638 Sq Ft
  • House for Rent

  1695 Lee Rd, Winter Park, FL 32789

  Don't miss out on this cozy 1-bedroom, 1-bathroom condo at Waterfall Cove. The unit has been newly painted throughout and features kitchen appliances, upgraded blinds, ceiling fans, and a full-size washer and dryer. You can also enjoy your morning coffee on the private patio. The community offers excellent amenities, including a pool, playground, and picnic area. Waterfall Cove is ideally located

  1695 Lee Rd, Winter Park, FL 32789
• 

  

  /70

  $5,200 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,514 Sq Ft
  • House for Rent

  5338 Ardsdale Ln, Orlando, FL 32814

  Rare opportunity to rent a beautiful single-family home in Baldwin Park. This stunning two-story Craftsman-style residence features a charming front porch overlooking a private mews and is just steps from the community pool. The home offers three bedrooms plus a spacious media or playroom, two and a half bathrooms, and a desirable first-floor primary suite. Interior highlights include gorgeous

  Carolina Brum WRA BUSINESS & REAL ESTATE

  5338 Ardsdale Ln, Orlando, FL 32814

Showing Results 41 - 67, Page 2 of 2