10

Winter Park, FL Houses for Rent with Community Pool

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  • /44

    $2,950 Per Month

    • 3 Beds
    • 2 Baths
    • 1,770 Sq Ft
    • House for Rent

    3463 Arnel Dr, Winter Park, FL 32792

    Beautiful pool home for rent in Winter Park located in the established Eastbrook community with NO HOA. This home offers 3 bedrooms plus a versatile bonus room, 2 bathrooms, approximately 1,770 sq ft of living space, a 2-car garage, extended driveway, and a private screened pool with fully fenced backyard. Inside, you’ll find a bright and functional layout with comfortable living and dining

    Agent Photo

    Alexa Monasterio Flores

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    3463 Arnel Dr, Winter Park, FL 32792
  • /19

    $2,830 Per Month

    • 4 Beds
    • 2 Baths
    • 1,756 Sq Ft
    • House for Rent

    5219 Ardmore Dr, Winter Park, FL 32792

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist

    5219 Ardmore Dr, Winter Park, FL 32792
  • /30

    $4,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,776 Sq Ft
    • House for Rent

    1791 Spruce Ave, Winter Park, FL 32789

    Beautifully renovated 3 bedroom, 2 bath pool home in one of Winter Park's most desirable neighborhoods. Designed with an open floor plan, this home features wood flooring throughout the main living areas, crown molding, and an incredible chef's kitchen with Quartz countertops, a large breakfast bar, custom cabinetry, floating wood shelves, gas range, stainless steel appliances, and abundant

    Agent Photo

    Jennifer King

    CORCORAN PREMIER REALTY

    1791 Spruce Ave, Winter Park, FL 32789
  • /20

    $2,550 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,482 Sq Ft
    • House for Rent

    3313 Hamlet Loop, Winter Park, FL 32792

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.Interested in this home? You clearly have exceptional taste. This charming 3-bedroom, 2.5-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    3313 Hamlet Loop, Winter Park, FL 32792
  • /11

    $2,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,482 Sq Ft
    • House for Rent

    1840 Bachman Way, Winter Park, FL 32792

    Property Id: 502903Amazing 3 bedroom, 2.5 bathroom house in Winter Park. Freshly painted home with vaulted ceiling throughout! Tile floor on 1st floor and carpet on 2nd floor. Spacious living room area. Great neighborhood with A+ Seminole County schools. Great location and close to schools, shopping and restaurants. Easy access to 436 and major highways. Amenities included: central air,

    1840 Bachman Way, Winter Park, FL 32792
  • /24

    $8,295 Per Month

    • 4 Beds
    • 5.5 Baths
    • 3,295 Sq Ft
    • House for Rent

    2234 Howard Dr, Winter Park, FL 32789

    Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park's most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility.Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal

    Raquel Elliott COLDWELL BANKER REALTY

    2234 Howard Dr, Winter Park, FL 32789
  • /14

    $1,750 Per Month

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

    2304 Inagua Way, Winter Park, FL 32792

    Welcome to this charming 2 bedroom, 1 bathroom corner unit in Winter Park, FL. This single-story home features ceramic tile flooring throughout, perfect for easy maintenance. The freshly painted interior complements the renovated kitchen and bathroom, giving the space a modern and updated feel. Enjoy the privacy of the fenced backyard, ideal for outdoor entertaining or relaxing. Located in the

    2304 Inagua Way, 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
  • /36

    $2,850 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,669 Sq Ft
    • House for Rent

    5530 S Lake Burkett Ln, Winter Park, FL 32792

    This charming two-story home situated on a serene conservation lot within the highly sought-after Trinity Bay community in Winter Park. The inviting entrance showcases a covered portico with decorative beams and brick accents. Inside, the spacious living room boasts soaring cathedral ceilings, distinctive round-top windows, and a cozy wood-burning fireplace. A second-story loft overlooks the

    Mostafa Boulhanna MNT INTERNATIONAL

    5530 S Lake Burkett Ln, Winter Park, FL 32792
  • /58

    $3,300 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,891 Sq Ft
    • House for Rent

    1843 Shadyhill Terrace, Winter Park, FL 32792

    Available for lease in the desirable Autumn Glen community of Winter Park. This spacious and well-maintained 4-bedroom, 2-bathroom single-family home offers comfort, space, and serenity in a peaceful neighborhood setting. Thoughtfully landscaped with lush greenery and tranquil water views, the home features an oversized kitchen with stainless steel appliances, ample storage, and a pass-through

    Beatrice Miranda METRO CITY REALTY

    1843 Shadyhill Terrace, Winter Park, FL 32792

Rental Home Trends

Number of Houses for Rent
10
Median Single Family Home Rent
$2,550
Median 3 Bedroom Single Family Home Rent
$2,500
Median 4 Bedroom Single Family Home Rent
$3,850
Median 5 Bedroom Single Family Home Rent
$5,650
How to Rent a Home