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Fully Furnished Homes for Rent in Winter Park, FL

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  • /40

    $14,000 Per Month

    • 3 Beds
    • 6 Baths
    • 4,027 Sq Ft
    • House for Rent

    2024 Lake Dr, Winter Park, FL 32789

    This beautiful, furnished home on Lake Killarney offers a rare opportunity to lease a luxury property on a skiable lake, complete with a private dock for your boat and jet ski. Enjoy scenic rides to popular local dining spots like Hillstone's or Shake Shack, or simply unwind in your own backyard, lounging by the saltwater infinity pool and cozying up around the outdoor fire pit. Inside, the home

    Agent Photo

    Jennifer King

    CORCORAN PREMIER REALTY

    (321) 384-7923

    2024 Lake Dr, Winter Park, FL 32789
  • /65

    $6,995 Per Month

    • 5 Beds
    • 4 Baths
    • 2,918 Sq Ft
    • House for Rent

    2075 Jewell Ave, Winter Park, FL 32789

    FULLY FURNISHED 5br/4b +bonus loft GEM! Welcome to 2075 Jewel Avenue, an exceptional residence nestled in the heart of Winter Park, 32789—one of Central Florida’s most sought-after communities. Ideally situated just minutes from the vibrant shops and dining along Park Avenue and the scenic beauty of Rollins College, this home offers the perfect blend of charm, convenience, and lifestyle. Set on a

    Agent Photo

    Paul Jimenez

    URBANISTA BROKERS

    (321) 483-3119

    2075 Jewell Ave, Winter Park, FL 32789
  • /62

    $3,900 Per Month

    • 4 Beds
    • 3 Baths
    • 2,130 Sq Ft
    • House for Rent

    1542 Sugarwood Cir, Winter Park, FL 32792

    Spacious, fully remodeled 4-bedroom, 2.5-bath single-family home located in the desirable Amberwood community in Winter Park. This one-story property offers approximately 2,130 sq ft of living space, featuring vaulted ceilings, a functional layout, and a bright living and dining area. The home showcases luxury finishes throughout, a brand-new roof, central A/C, and a 2-car attached garage. Enjoy

    Dayana Perez Moreno AROD PARTNERS REALTY

    1542 Sugarwood Cir, Winter Park, FL 32792
  • /19

    $1,995 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    1942 Conifer Ct, Winter Park, FL 32792

    Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a talbe with 4 chairs - picnic in your own park

    Scott Banta BLACKFIN REALTY LLC

    1942 Conifer Ct, Winter Park, FL 32792
  • /15

    $4,100 Per Month

    • 4 Beds
    • 2 Baths
    • 1,764 Sq Ft
    • House for Rent

    2344 Woodcrest Dr, Winter Park, FL 32792

    Resort Style Pool Home in KENILWORTH ESTATES! Conveniently located in Winter Park with a walking distance to Baldwin Park, Advent Health, Cody trail park! A short drive to Renown Rollin College, Park Ave, Full Sail University, downtown Orlando, theme parks, and UCF! Close to restaurants, shopping centers, bars, Publix, CVS and gas stations. Welcome Home! through the main door, you will be amazed

    SHANNON LEE EXPLORE FLORIDA REALTY SERVICES LLC

    2344 Woodcrest Dr, Winter Park, FL 32792
  • /37

    $3,900 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,196 Sq Ft
    • House for Rent

    Unlisted Address

    This beautiful new two-story home, high ceiling and fully equipment kitchen, located in Winter Park’s exclusive gated community of Hawk’s Crest. Community has lake access with canon launch. This home was build by Taylor Morrison comes with 4-bedroom, 2.5 bathroom home has a great open floor plan that features open dining and living rooms that look out to the lanai and backyard. Home comes all

    Elaine Zheng HONEST REAL ESTATE COMPANY

    Unlisted Address
  • /15

    $1,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft
    • Condo for Rent

    7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792

    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 within reach of central Florida's vibrant offerings. Strategically positioned minutes from the

    David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

    7429 Daniel Webster Dr Unit 14 (C), 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
$2,650
Median Townhouse Rent
$2,490
Median Condo Rent
$1,630
How to Rent a Home