688

Winter Park, FL Homes for Rent

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  • /88

    $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
  • /13

    $1,445 Per Month

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

    7302 Swallow Run Unit 7302, Winter Park, FL 32792

    AVAILABLE NOW! Please call or text to schedule a showing. This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35

    7302 Swallow Run Unit 7302, Winter Park, FL 32792
  • /27

    $4,400 Per Month

    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • House for Rent

    648 Fitzwalter Dr, Winter Park, FL 32792

    Nestled beside Cady Way Park & Trail, this charming home offers an unbeatable location in a quiet, established neighborhood on a peaceful tree-lined cul-de-sac. Enjoy easy access to top-rated Winter Park schools, Winter Pines Golf Club, Showalter Field, AdventHealth Winter Park, Baldwin Park, Downtown Winter Park, and a wide variety of shopping, dining, and entertainment. Inside, you’ll find

    Paul Chisholm LOVEJOY PROFESSIONAL REALTY, INC

    648 Fitzwalter Dr, Winter Park, FL 32792
  • /22

    $2,300 Per Month

    • 3 Beds
    • 2 Baths
    • 1,437 Sq Ft
    • Winter Park Home For Rent

    2267 Coventry Dr, Winter Park, FL 32792

    This home offers a split plan, 3-bedroom, 2-bath, 2 Car Garage home that is ready to move in, with a fenced backyard and in the prime location of the Winter Woods subdivision in Winter Park. This home offers freshly painted walls, a newer roof, newer exterior paint and lights, windows, plumbing, and an updated kitchen with an island open to the living room. The kitchen offers granite countertops,

    2267 Coventry Dr, Winter Park, FL 32792
  • /15

    $1,500 Per Month

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

    Unlisted Address

    2 Bedrooms, 1 Bathroom located on the first floor. IGalley kitchen (with a dishwasher, microwave, range, refrigerator, and a washer/dryer combo), walk-in closet in the primary bedroom, and an open living/dining room combo filled with natural light. A private patio, playground, and park. It includes 1 assigned parking space.

    Kirsten Cantello TRUSTHOME PROPERTIES INC

    Unlisted Address
  • /21

    $1,250 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Spacious and Affordable 2/2 Condo In Lancelot at Winter Park

    3651 N Goldenrod Rd Unit B202, Winter Park, FL 32792

    AVAILABLE NOW!!! This beautiful 2 bedroom, 2 bathroom condo in the Lancelot at Winter Park community near local shops, restaurants, and schools. Features include tile throughout, vaulted ceilings, kitchen with stainless appliances and breakfast bar, two full bathrooms, and spacious bedrooms. Community amenities include a pool and clubhouse. MUST SEE! Won't last long! Schedule your showing

    3651 N Goldenrod Rd Unit B202, Winter Park, FL 32792
  • /43

    $4,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,345 Sq Ft
    • House for Rent

    344 Starling Rd, Winter Park, FL 32789

    For Rent – Beautifully Updated Home Near Lake Killarney!Located just minutes from Downtown Winter Park, Park Avenue, I-4, and Maitland, this beautifully updated home offers convenient access to nearby shops and dining. The 3-bedroom, 3-full-bath layout features open living spaces and modern finishes throughout. LVP flooring flows through the entire home, complemented by fresh paint, abundant

    Kelly Price KELLY PRICE & COMPANY LLC

    344 Starling Rd, Winter Park, FL 32789
  • /9

    $2,015 Per Month

    • 3 Beds
    • 2 Baths
    • 1,175 Sq Ft
    • Condo for Rent

    2711 Aloma Ave, Winter Park, FL 32792

    Welcome home to 2711 Aloma Avenue — a 3-bedroom, 2-bathroom unit offering 1,175 square feet in the Winter Park area near Orlando. This home offers a comfortable, well-proportioned layout convenient to Aloma Avenue shopping, dining, and easy access to major roadways for commuting throughout the greater Orlando area. Pet-friendly with a pet fee. For applications or to schedule a viewing, please

    2711 Aloma Ave, Winter Park, FL 32792
  • /25

    $1,650 Per Month

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

    3374 Cedar Springs Place Unit 155, Winter Park, FL 32792

    2br 2.5ba UPDATED home in Hidden Oaks, Winter Park!!! Kitchen UPDATED with GRANITE counters and solid wood cabinets, upgraded toilets throughout, updated sinks & faucets in all baths. TILE FLOORS downstairs with neutral tone carpet on stairs and second floor. Dry bar area in living room. Both bedrooms are upstairs, each with their own full bathroom! Half bath downstairs off the living/dining room

    Greg Mann BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P

    3374 Cedar Springs Place Unit 155, Winter Park, FL 32792
  • /15

    $2,195 Per Month

    • 4 Beds
    • 2 Baths
    • 1,669 Sq Ft
    • House for Rent

    2730 Prince John Rd, Winter Park, FL 32792

    Fantastic 4 Bed 2 Bath Winter Park Home with 2-car garage! Located in a highly desirable Winter Park area. Large living room/dining room combo, a large separate den area. The home has a large fenced-in backyard. Lawn care is included. Walking distance to the Cady Way Trail. *Bonus Amenity Included* -All RE/MAX 200 Realty Property Management Division residents are enrolled in the Resident

    2730 Prince John Rd, Winter Park, FL 32792
  • /44

    $6,300 Per Month

    • 3 Beds
    • 3 Baths
    • 2,434 Sq Ft
    • Townhouse for Rent

    1136 S Pennsylvania Ave, Winter Park, FL 32789

    Welcome home to this beautifully appointed end-unit Georgetown townhome in the highly desirable Virginia Heights community. Ideally located just minutes from Rollins College, Park Avenue, and the best shopping, dining, and entertainment that Winter Park has to offer, this exceptional residence offers the perfect blend of elegance, comfort, and convenience. Step inside to discover a bright, open

    Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1136 S Pennsylvania Ave, Winter Park, FL 32789
  • /21

    $2,350 Per Month

    • 2 Beds
    • 2 Baths
    • 1,074 Sq Ft
    • 55+ Winter Park Condo

    700 Melrose Ave, Winter Park, FL 32789

    Beautifully upgraded 2-bedroom, 2-bath condo in the heart of Winter Park! Located in a sought-after 55+ community surrounded by mature, lush landscaping, this charming condo offers the perfect blend of comfort and convenience. Enjoy a short walk to Mead Botanical Garden or the shops, dining, and entertainment along Park Avenue. With easy access to I-4, downtown Orlando, hospitals, shopping, and

    700 Melrose Ave, Winter Park, FL 32789
  • /12

    $3,400 Per Month

    • 4 Beds
    • 3 Baths
    • 2,319 Sq Ft
    • House for Rent

    7903 Pleasant Pine Cir, Winter Park, FL 32792

    WINTER PARK 4 BR / 3BA + BONUS ROOM, built in 2014. Located in the GATED COMMUNITY of Enclave At Aloma. All bedrooms are on the FIRST FLOOR, including the master bedroom with space for a king size bed and a HUGE WALK-IN CLOSET. The family room opens to the kitchen with 42" wood cabinets, white QUARTZ counter tops, STAINLESS STEEL appliances, KITCHEN ISLAND with breakfast bar seating and a large

    Elizabeth Beaudoin PR REAL ESTATE SERVICES

    7903 Pleasant Pine Cir, Winter Park, FL 32792
  • /29

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,782 Sq Ft
    • Townhouse for Rent

    2895 Clever Ln, Winter Park, FL 32792

    Welcome home to 2895 Clever Lane, a three bedroom, two and a half bath corner unit with a two-car garage! The kitchen overlooks the main living area and features a full suite of stainless-steel appliances including the refrigerator, range, over the range microwave and dishwasher as well as plenty of cabinetry and countertop space. The half bath is located on the first floor, easily accessible for

    2895 Clever Ln, Winter Park, FL 32792
  • /24

    $2,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Condo for Rent

    150 Killarney Bay Ct Unit 5-5, Winter Park, FL 32789

    Welcome to this beautifully updated first-floor 2-bedroom, 2-bath condo in the highly desirable Killarney Bay community in Winter Park, offering a perfect blend of comfort, style, and lakefront living. Step inside to an inviting open-concept layout filled with natural light and designed for both everyday living and entertaining. The modern kitchen features upgraded cabinetry, sleek countertops,

    Giovanna D'Alessandro RP INVESTMENT REALTY LLC

    150 Killarney Bay Ct Unit 5-5, Winter Park, FL 32789
  • /32

    $3,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft
    • Winter Park Charmer

    1816 Mizell Ave, Winter Park, FL 32789

    Experience the best of Winter Park living in this charming 3-bedroom, 2-bathroom rental home! Located just minutes from Baldwin Park, Park Avenue, top-rated restaurants, and tons of shopping, this home offers both convenience and style. Enjoy Saturday mornings at the local farmers market and peaceful evening strolls through the beautiful Windsong neighborhood. Plus, UCF and Full Sail University

    1816 Mizell Ave, Winter Park, FL 32789
  • /23

    $5,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,405 Sq Ft
    • Property for Rent

    616 Ellendale Dr, Winter Park, FL 32792

    Virtually Staged. Move right into this beautifully updated pool home in the highly desirable Winter Park Estates community, offering an exceptional combination of storage space, flexibility, and location. New A/C (2026), Freshly painted throughout (2026), New Kitchen Countertops coming soon (2026) this move-in-ready home features an open-concept layout filled with natural light, seamlessly

    Elena Sanchez BALDWIN PARK REALTY LLC

    616 Ellendale Dr, Winter Park, FL 32792
  • /30

    $9,500 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,714 Sq Ft
    • Winter Park lakefront just steps from Park Avenue

    660 Osceola Ave, Winter Park, FL 32789

    Experience the best of Winter Park waterfront living in this beautifully updated ground-floor residence at Perle du Lac, ideally located just a short stroll from the boutiques, restaurants, and cafés of Park Avenue. Even more rare, this exceptional residence includes a private covered boat slip on the pristine waters of Lake Virginia, offering direct access to the renowned Winter Park Chain of

    660 Osceola Ave, Winter Park, FL 32789
  • /14

    $1,600 Per Month

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

    1695 Lee Rd Unit C103, Winter Park, FL 32789

    Charming condo for Lease! location , Location , location ! This 2-bedroom, 1-bathroom apartment offers an open layout with plenty of natural light, a spacious living area, and a well-equipped kitchen with brand new interior paint job.Enjoy the convenience of in-unit laundry and modern amenities throughout. The apartment is situated in a serene community, offering easy access to shopping, dining,

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit C103, Winter Park, FL 32789
  • /23

    $2,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,790 Sq Ft
    • 3/2.5 townhouse in gated Winter Park community

    2479 Passamonte Dr, Winter Park, FL 32792

    Introducing a charming 3-bedroom, 2.5-bathroom townhouse in the gated Winter Park community of Via Lago at Hanging Moss. This two-story townhouse located in the Winter Park High School district, features a convenient 1-car garage, stainless steel appliances and includes washer and dryer. All bedrooms are on the second floor. Enjoy the Florida weather on the screened porch, ideal for relaxing or

    2479 Passamonte Dr, Winter Park, FL 32792
  • /20

    $1,600 Per Month

    • 2 Beds
    • 1.5 Baths
    • 825 Sq Ft
    • Townhouse for Rent

    2523 Alexa Ct, Winter Park, FL 32792

    Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard

    Bernardo Reynoso LA ROSA REALTY LLC

    2523 Alexa Ct, Winter Park, FL 32792
  • /25

    $1,800 Per Month

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

    2510 Boyd Ave, Orlando, FL 32803

    Step into the allure of this meticulously renovated one-bedroom and bathroom apartment unit. The open-concept space boasts a granite countertop and stainless steel appliances, creating a modern and inviting ambiance. The unit also features an extra room, perfect for an office, with direct access to the private backyard. Conveniently situated near Baldwin Park, downtown Orlando, and a plethora of

    2510 Boyd Ave, Orlando, FL 32803
  • /46

    $2,750 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
  • /12

    $1,990 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft
    • House for Rent

    825 Driver Ave, Winter Park, FL 32789

    COMING SOON: Dubsdread neighborhood...This clean & charming bungalow is located on a quiet street with updated & substantial homes in the Dubsdread neighborhood of Winter Park, less than 1/2 mile to I-4 ramp at Fairbanks. The home features an updated eat-in kitchen (with black stainless appliances) & updated bathrooms. New washer/dryer, a garage, extra parking pad & a covered patio. Faux wood

    825 Driver Ave, Winter Park, FL 32789
  • /22

    $2,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,614 Sq Ft
    • House for Rent

    912 Carvell Dr, Winter Park, FL 32792

    Nestled in the sought-after Winter Park Estates neighborhood, this beautifully maintained 3-bedroom, 2-bathroom pool home offers the perfect blend of classic charm and modern updates. Step through the front door into a warm, welcoming living room that flows effortlessly into a dining area featuring updated kitchen finishes and quality appliances.The spacious family room offers flexible living

    Grace Feng INTOP REALTY LLC

    912 Carvell Dr, Winter Park, FL 32792
  • /20

    $2,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,399 Sq Ft
    • House for Rent

    3086 Bluebrook Dr, Winter Park, FL 32792

    Minimum Deposit $2,200. Monthly Rent $2,200. Available August 10th!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 home to this charming 3-bedroom, 2-bathroom single-family home in the highly desirable Winter Park

    3086 Bluebrook Dr, Winter Park, FL 32792
  • /18

    $3,150 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,803 Sq Ft
    • Townhouse for Rent

    1409 Michigan Ave, Winter Park, FL 32789

    Available for September move-in! Welcome home to this spacious 3-bedroom, 2.5-bath townhome in the heart of Winter Park. Thoughtfully designed with an open and functional floor plan, this home offers comfortable living, stylish finishes, and abundant natural light throughout. The first floor features a spacious living area and a separate dining room/flex space, perfect for formal dining, a home

    Kyle Li UNIONE REALTY INC

    1409 Michigan Ave, Winter Park, FL 32789
  • /14

    $1,500 Per Month

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

    1695 Lee Rd Unit Apartment A103, Winter Park, FL 32789

    2 Bedrooms, 1 Bathroom located on the first floor. IGalley kitchen (with a dishwasher, microwave, range, refrigerator, and a washer/dryer combo), walk-in closet in the primary bedroom, and an open living/dining room combo filled with natural light. A private patio, playground, and park. It includes 1 assigned parking space.This property offers an option of a security deposit-free lease

    1695 Lee Rd Unit Apartment A103, Winter Park, FL 32789
  • /2

    $2,750 Per Month

    • 3 Beds
    • 2 Baths
    • 1,030 Sq Ft
    • House for Rent

    1303 Canterbury Rd, Winter Park, FL 32789

    Welcome to this charming 3-bedroom, 2-bathroom home in the highly sought-after Orwin Manor neighborhood of Winter Park. This move-in ready home features an open floor plan, updated kitchen, luxury vinyl flooring, and abundant natural light throughout. Enjoy a spacious corner lot with a private patio and generous backyard, perfect for relaxing or entertaining. Conveniently located just minutes

    Paula Wells PRIMAC GROUP, INC

    1303 Canterbury Rd, Winter Park, FL 32789
  • /16

    $1,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Excellent location

    4968 Tangerine Ave Unit 4968, Winter Park, FL 32792

    This roomy condo is available for immediate occupancy. New Luxury Vinyl Plank floors just installed. The unit is ideally located in Winter Park, not far from Full Sail or UCF. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet community with plenty of privacy. Amenities include a pool and workout room. Call today for your private tour of this amazing

    4968 Tangerine Ave Unit 4968, Winter Park, FL 32792
  • /16

    $1,500 Per Month

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

    7340 Swallow Run Unit 7340, Winter Park, FL 32792

    Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.

    Jennifer Linton METRO CITY REALTY

    7340 Swallow Run Unit 7340, Winter Park, FL 32792
  • /13

    $2,099 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,550 Sq Ft
    • Townhouse for Rent

    2648 Galliano Cir, Winter Park, FL 32792

    ***New residents will receive three (3) complimentary months of the Resident Benefits Package (RBP). Take advantage of this exclusive offer and enjoy added benefits at no cost for your first three months!***This property will not last long! Schedule a showing today! Winter Park Two Story 2/2.5 Townhome located in the Private - Gated Community of Vistas at Lake Howell. All Stainless Steel

    2648 Galliano Cir, Winter Park, FL 32792
  • /13

    $1,600 Per Month

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

    3651 N Goldenrod Rd Unit 103, Winter Park, FL 32792

    Super nice, 2 bed/2 bath, ground floor unit. Wonderful open floor plan, laminate and tile flooring, updated bathrooms, all kitchen appliances, washer and dryer, and ceiling fans. Water is included. No Pets Allowed. Conveniently located. Call today for an appointment! EQUAL HOUSING OPPORTUNITY

    Kelly Carr CFRP REALTY LLC

    3651 N Goldenrod Rd Unit 103, Winter Park, FL 32792
  • /14

    $4,200 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,667 Sq Ft
    • House for Rent

    2856 Kemper Ave, Orlando, FL 32814

    Live and play in the center of it all!! Newly REMODELED with beautiful quartz tops/backsplash in the Kitchen, Master Bath and secondary baths, new bath faucets, all new wood look ceramic tile flooring, new baseboards/paint, and epoxy garage flooring. Wonderful family home in Baldwin Park convenient to downtown Baldwin Park and the Park Avenue shopping district. Walk to Glenridge Middle School,

    Nancy Woodruff WOODRUFF REALTY, INC.

    2856 Kemper Ave, Orlando, FL 32814
  • /18

    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,812 Sq Ft
    • House for Rent

    622 Green Meadow Ave, Maitland, FL 32751

    NOW AVAILABLE! Wonderful Seminole County 3/2/2 block home in a favorite established Maitland neighborhood with underground utilities and sidewalks. LAWN CARE INCLUDED TOO! Ranch style home with nicely covered front patio and court yard perfect for potted paints and outdoor furniture. Huge open concept floor plan with the kitchen, dining room and great room wide open with 2 sets of french doors

    Sheryl Webster VENTURE HOME REALTY

    622 Green Meadow Ave, Maitland, FL 32751
  • /7

    $1,800 Per Month

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

    2510 Boyd Ave Unit b, Orlando, FL 32803

    Experience the allure of this meticulously renovated one-bedroom and bathroom apartment unit. This open-concept space features a granite countertop and stainless steel appliances, providing a modern and inviting atmosphere. Additionally, the unit includes an extra room, ideal for an office, with direct access to the private backyard. Conveniently located near Baldwin Park, downtown Orlando, and a

    Antonio Velazquez BP REALTY

    2510 Boyd Ave Unit b, Orlando, FL 32803

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