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Winter Park, FL Homes for Rent with Water View

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  • /39

    $7,900 Per Month

    • 4 Beds
    • 3 Baths
    • 2,476 Sq Ft
    • House for Rent

    300 Killarney Dr, Winter Park, FL 32789

    Exceptional Lakefront Living in the Heart of Winter ParkWelcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location. This exquisite 4-bedroom, 3-bath home presents a rare opportunity to enjoy Winter Park's coveted lifestyle.Property Highlights:Situated on an oversized lot with coveted Lake Killarney

    Kelly Price KELLY PRICE & COMPANY LLC

    300 Killarney Dr, Winter Park, FL 32789
  • /24

    $3,200 Per Month

    • 2 Beds
    • 1 Bath
    • 1,250 Sq Ft
    • House for Rent

    438 Lakeview Ave, Winter Park, FL 32789

    Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete

    Alex Scures COLONIALTOWN REALTY

    438 Lakeview Ave, Winter Park, FL 32789
  • /24

    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Condo for Rent

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

    Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

    Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

    151 N Orlando Ave Unit 118, 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
  • /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
  • /41

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,837 Sq Ft
    • Condo for Rent

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

    REMODELLED - new flooring and freshly painted. Welcome home to this beautiful townhome centrally located in Winter Park, 15 miles away from Park Avenue, just outside of Baldwin Park. Enjoy beautiful water views on the back patio. This home is fresh ready to move in. Available for rent April 15 or later. Top schools, Glenridge middle school, Winter Park high school and Brookshire elementary

    Livia Petraru EXP REALTY LLC

    2530 Passamonte Dr Unit 10E, Winter Park, FL 32792
  • /46

    $3,150 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft
    • Townhouse for Rent

    1351 Merrydale Way, Winter Park, FL 32792

    Fantastic, Modern townhome WITH 3 beds & 2.5 baths. Hawk's Crest is a gated community in Winter Park. This home is has a very spacious open floor plan with a water view! The kitchen has granite countertops and is fully equipped with stainless steel Whirlpool appliances; oven, stove, microwave, refrigerator, dishwasher, and garbage disposal. The kitchen area also has a large pantry! This energy

    Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

    1351 Merrydale Way, Winter Park, FL 32792
  • /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

Rental Home Trends in Winter Park, FL

Rental Home Trends

Number of Homes for Rent
8
Median Rent
$2,095
Median Single Family Home Rent
$2,647
Median Townhouse Rent
$2,450
Median Condo Rent
$1,650
How to Rent a Home