Winter Park Real Estate for Rent by Neighborhood

Find Winter Park Real Estate for Rent by clicking on the relevant neighborhood.

View all Winter Park Real Estate for Rent

AMBERWOOD UNIT 1 real estate for rent ARROWHEAD COVE real estate for rent
AUTUMN GLEN PH 2 real estate for rent BROOKSHIRE HEIGHTS real estate for rent
COLONIES real estate for rent CORONATION ADD real estate for rent
DIXIE TERRACE real estate for rent DUBSDREAD HEIGHTS real estate for rent
EASTBROOK SUB UNIT 06 real estate for rent EASTBROOK SUB UNIT 07 real estate for rent
EASTBROOK SUB UNIT 11 real estate for rent EASTBROOK SUB UNIT 13 real estate for rent
ENCLAVE AT HAWKS CREST real estate for rent FERNBROOK TRAILS PH 3 real estate for rent
FOUR SEASONS CONDO real estate for rent GEORGEANN ESTATES real estate for rent
GOLFSIDE SEC 03 real estate for rent GOLFSIDE VILLAS CONDO real estate for rent
GRAYSON SQUARE real estate for rent GREEN OAKS REP real estate for rent
GREENVIEW AT WINTER PINES real estate for rent HAWKS CREST real estate for rent
HENKELS ADD/WINTER PARK real estate for rent HIDDEN OAKS CONDO PH 01 real estate for rent
HIDDEN OAKS CONDO PH 08 real estate for rent HIDDEN OAKS CONDO PH 10 real estate for rent
HORTON AARON real estate for rent JUSTAMERE CAMP REP real estate for rent
KAROLINA ON KILLARNEY real estate for rent KENILWORTH ESTATES 1ST ADD real estate for rent
KENILWORTH SHORES SEC 06 real estate for rent KENILWORTH SHORES SEC 07 real estate for rent
KILLARNEY BAY CONDO real estate for rent KILLARNEY ESTATES real estate for rent
LAKE KILLARNEY CONDO real estate for rent LAKE KNOWLES TERRACE ADD 02 real estate for rent
LAKE WAUNATTA WOODS real estate for rent LAKEMONT ESTATES real estate for rent
LAKEMONT HEIGHTS real estate for rent LANCELOT/WINTER PARK real estate for rent
LAWNDALE real estate for rent MEADOWS AT HAWKS CREST real estate for rent
MONDRIAN/WINDER PARK TWNHMS real estate for rent ORWIN MANOR WESTMINSTER SEC real estate for rent
PARK AIRE CONDO real estate for rent PARKVIEW VILLAGE real estate for rent
PARKVIEW VILLAGE CONDOMINIUM real estate for rent PENNSYLVANIA STATION 01 CONDO real estate for rent
SOUTH LAKEMONT SHORES real estate for rent STANSBURY ESTATES real estate for rent
STRATFORD A WINTER PARK CONDO real estate for rent TUSCANY PLACE FIRST ADD real estate for rent
TUSCANY TERRACE real estate for rent VIA LAGO/HANGING MOSS PH 09 real estate for rent
VISTAS AT LAKE HOWELL real estate for rent WATERFALL COVE real estate for rent
WATERS EDGE AT HAWKS CREST real estate for rent WHISPERWOOD CONDO 02 real estate for rent
WINDWARD SQUARE SEC 3 real estate for rent WINTER PARK real estate for rent
WINTER PARK PINES real estate for rent WINTER PARK VILLAS CONDO real estate for rent
WRENWOOD CONDO real estate for rent

Newest Real Estate in Winter Park by Neighborhood

View all Winter Park Real Estate for Rent

  • 640 N PARK AVE #5, WINTER PARK, FL - MLS# O6411306

    PARK AIRE CONDO - O6411306 - 640 N PARK AVE #5, WINTER PARK, FL 32789
    1 Day on yellowkey

    $3,200 | Condo | 1 beds | 1.0 baths | 1 gar

    One or more photo(s) has been virtually staged. Welcome to Park Aire, a small iconic condo community located on Park Avenue by the WP9 golf course. 1st floor unit with oversized window views of the golf course and Casa Feliz. This one bedroom unit has an updated kitchen and bath. Amenities include a covered parking space, swimming pool, social room, a guest room for rent, open air patios on the third floor, under building covered parking spot and laundry in building garage and 2nd floor. You are close by for shopping and dining along Park Ave area.

    Contact Yellowkey Agent

    Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY

  • 1119 S PENNSYLVANIA AVE, WINTER PARK, FL - MLS# O6411654

    - O6411654 - 1119 S PENNSYLVANIA AVE, WINTER PARK, FL 32789
    1 Day on yellowkey

    $5,200 | Townhouse | 4 beds | 3.0 baths | 1 gar

    Welcome home to this beautifully updated Cherokee Park townhome, where modern elegance meets comfort in the heart of highly desirable Winter Park. Perfectly situated near some of the area’s best dining, shopping, and entertainment, this home offers both luxury and convenience in one exceptional location. Step inside to a bright and airy open-concept living space featuring wood-style flooring, soaring vaulted ceilings, and a sleek modern fireplace that creates a warm yet contemporary focal point. Large windows throughout flood the home with natural light, including a stunning arched window overlooking lush greenery for a peaceful and inviting atmosphere. The thoughtfully updated kitchen and bathrooms feature clean contemporary finishes, stone countertops, designer lighting, and premium frameless glass showers. Fresh interiors, updated fixtures, and organized closet shelving make this home completely move-in ready with both style and functionality in mind. Upstairs, spacious bedrooms offer comfort and privacy with abundant natural light and spa-inspired bathrooms designed for relaxation. Step outside to your own private backyard retreat featuring low-maintenance luxury landscaping, pristine white stone accents, and premium artificial turf that keeps the outdoor space vibrant year-round. The fully fenced yard is perfect for relaxing evenings, entertaining guests, or enjoying peaceful mornings outdoors. Located just minutes from the renowned shops and restaurants of Park Avenue, residents will enjoy easy access to boutique shopping, fine dining, local cafés, and everyday conveniences including Trader Joe's. You’re also close to scenic parks, Lake Virginia, and Rollins College, making this location ideal for those seeking an active and connected lifestyle. Zoned for highly rated Winter Park schools and professionally managed by Atrium Management, this home offers the perfect combination of style, location, and convenience.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY

  • 620 TRINIDAD CT #620, WINTER PARK, FL - MLS# S5150729

    WINTER PARK VILLAS CONDO - S5150729 - 620 TRINIDAD CT #620, WINTER PARK, FL 32792
    3 Days on yellowkey

    $1,725 | Single Family Home | 2 beds | 2.0 baths

    Beautifully Renovated 2-Bedroom Home in Desirable Winter Park! Welcome to this charming newly renovated 2-bedroom, 2-bath home located in the highly desirable Winter Park area. Featuring modern upgrades and a warm, inviting layout, this home offers the perfect blend of comfort and style. Enjoy ceramic tile flooring throughout the first floor, brand-new carpet in the upstairs bedroom, and a beautifully updated kitchen complete with new cabinets and appliances for a fresh contemporary feel. Step outside to your own private fenced yard—perfect for relaxing, entertaining, or enjoying peaceful outdoor living. Residents also have access to fantastic community amenities, including a swimming pool and tennis courts for recreation and leisure. Conveniently located near shopping, dining, parks, and everything Winter Park has to offer, this move-in-ready home is an opportunity you won’t want to miss. Schedule your showing today!

    Contact Yellowkey Agent

    Listing is courtesy of: TRANSCEND REALTY

  • 1415 HARMON AVE, WINTER PARK, FL - MLS# O6407290

    HENKELS ADD/WINTER PARK - O6407290 - 1415 HARMON AVE, WINTER PARK, FL 32789
    3 Days on yellowkey

    $3,060 | Townhouse | 3 beds | 2.5 baths | 2 gar

    In the heart of Winter Park on a quiet cobbled street, this Mediterranean style 3-bedroom, 3-bathroom house is available to rent today. With beautiful Travertine floors throughout the downstairs of the home, granite countertop kitchen, marble countertop bathrooms, and limestone ornate pillars throughout the home, this home boasts character. Upstairs the home enjoys three bedrooms, two bathrooms, two balconies, and an upstairs utility room. The powder room is downstairs, and patio and a nice size back garden that the tenant can tend to as their own. The front of the house is a brick courtyard. New stainless-steel fridge 2023. 0.9 miles from Rollins College. Perfect for three tenants. Call today Weeks and Months Available

    Contact Yellowkey Agent

    Listing is courtesy of: LA ROSA REALTY ORLANDO LLC

  • 7338 SWALLOW RUN #7338, WINTER PARK, FL - MLS# O6411093

    WHISPERWOOD CONDO 02 - O6411093 - 7338 SWALLOW RUN #7338, WINTER PARK, FL 32792
    3 Days on yellowkey

    $1,650 | Condo | 2 beds | 2.0 baths

    Beautiful and affordable 2-bedroom, 2-bath condominium for rent in desirable East Winter Park! This renovated and move-in-ready unit features an open floor plan with modern plank-style tile flooring throughout the living areas, neutral colors, and plenty of natural light. The updated kitchen offers newer cabinets, countertops, appliances, and a stylish backsplash, creating a modern and functional space. Both bathrooms have been upgraded with newer vanities and finishes. The carpet was replaced in 2020 for added comfort. The spacious primary bedroom includes a large walk-in closet and a private en-suite bathroom. A stackable washer and dryer, only one year old, are also included for your convenience. Located just steps from the community pool, this well-maintained community is conveniently close to Full Sail University, Valencia College, and University of Central Florida. Enjoy easy access to major highways, shopping, dining, and entertainment, while being only a short drive from Park Avenue. Zoned for highly sought-after Winter Park schools.

    Contact Yellowkey Agent

    Listing is courtesy of: DOUGLAS EDMUND REAL ESTATE LLC

  • 517 LONDON RD, WINTER PARK, FL - MLS# O6410976

    WINTER PARK PINES - O6410976 - 517 LONDON RD, WINTER PARK, FL 32792
    4 Days on yellowkey

    $2,500 | Single Family Home | 3 beds | 2.0 baths | 2 gar

    Nestled in the highly sought-after Winter Park school district, this spacious 3-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and location. Featuring an expansive floor plan with generously sized living areas, this home provides plenty of room to relax, entertain, and enjoy everyday living. Ideally situated just minutes from premier shopping, popular restaurants, movie theaters, and everyday conveniences, you'll love having everything you need right at your fingertips. Outdoor enthusiasts will appreciate the close proximity to the scenic Cady Way Trail, offering miles of paved paths perfect for walking, jogging, and biking. Inside, the home boasts bright and inviting living spaces, a well-appointed kitchen with ample storage and workspace, spacious bedrooms, and two full baths. The large backyard provides additional space for outdoor gatherings, pets, or simply enjoying Florida's beautiful weather. Enjoy the best of Winter Park living in a home that combines size, location, and convenience in one exceptional rental opportunity.

    Contact Yellowkey Agent

    Listing is courtesy of: ANNE ROGERS REALTY GROUP INC

  • WINTER PARK, FL - MLS# O6409507

    MEADOWS AT HAWKS CREST - WINTER PARK, FL 32792
    4 Days on yellowkey

    $3,900 | Single Family Home | 4 beds | 2.5 baths | 2 gar

    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 premium appliances, chandeliers light fixtures with tractable fans in every room as well as smart home Alexa control switches. All of the existing security cameras and alarms can convey to you. Extended backyard with screened patio overseas a beautiful fountain pond view. The community features a resort style swimming pool, fitness center, splash pad, clubhouse, playgrounds, dog park, and access to a dock on Lake Howell where you can enjoy fishing and kayaking. Rental fee includes lawn care and irrigation for the best of maintenance free living. Come take a look.

    Contact Yellowkey Agent

    Listing is courtesy of: HONEST REAL ESTATE COMPANY

  • 7426 WYNNEWOOD SQ #195, WINTER PARK, FL - MLS# O6410726

    HIDDEN OAKS CONDO PH 10 - O6410726 - 7426 WYNNEWOOD SQ #195, WINTER PARK, FL 32792
    5 Days on yellowkey

    $1,800 | Condo | 3 beds | 2.0 baths | 2 gar

    3-bedroom and 2-bath condominium on Goldenrod Rd in Winter park . Newly renovated. Private end unit. Ground floor. Tile floor entirely. The unit features a functional layout and a highly desirable location near UCF, Full Sail University, Valencia College, and major shopping and dining. Landlord is looking for tenants with proof of income, credit and background checks. Schedule a tour.

    Contact Yellowkey Agent

    Listing is courtesy of: SPRINGHILL PROPERTIES LLC

  • 1404 CLAY ST, WINTER PARK, FL - MLS# O6410414

    ORWIN MANOR WESTMINSTER SEC - O6410414 - 1404 CLAY ST, WINTER PARK, FL 32789
    5 Days on yellowkey

    $2,800 | Single Family Home | 3 beds | 2.0 baths

    FOR RENT | Available June 1st | Winter Park – Orwin Manor Area | Washer & Dryer in-unit | Lawn Maintenance included. Charming 3-bedroom, 2-bathroom updated residence. Offering 1,440 sq ft of comfortable living space, this older home blends character with modern updates and an unbeatable location. Step inside to find updated kitchen, bathrooms, vinyl flooring, abundant natural light, and a functional layout designed for everyday living. The home features an interior laundry room with washer and dryer included for added convenience. Enjoy outdoor living in the large, fully fenced backyard, for play & dogs. Lawn maintenance is included! Location truly is everything. Situated just 2 minutes from I-4, this home provides quick access to Downtown Orlando while keeping you close to some of Central Florida’s favorite destinations. You'll be within 10 minutes from Publix, Trader Joe’s, Winter Park Village, and Park Avenue, where you can enjoy boutique shopping, dining, and nearby Rollins College. You’ll have a new place to go to every weekend! PLEASE NOTE: A separate mother-in-law suite is located on the property and is currently occupied by a tenant. Call today for application or more info!

    Contact Yellowkey Agent

    Listing is courtesy of: MEP REALTY INVESTMENTS LLC

  • 2344 WOODCREST DR, WINTER PARK, FL - MLS# O6410619

    KENILWORTH ESTATES 1ST ADD - O6410619 - 2344 WOODCREST DR, WINTER PARK, FL 32792
    5 Days on yellowkey

    $4,100 | Single Family Home | 4 beds | 2.0 baths | 2 gar

    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 by its modern and spacious floor plan! A lovely living room with a fireplace, an extra room for home gym or office, on the right, a sparkling pool in front of your eyesight through a modern glass sliding door, sitting under porch, enjoying family gathering in this resort style garden! There has a plenty closet space for storage. Spacious kitchen cabinets for cooking supplies. Be ready to live in a luxury and breath-taking Winter Park Pool home, while enjoying all Florida sunshine and outdoor biking, jogging and golfing at Winter Park Pine. Move in today!

    Contact Yellowkey Agent

    Listing is courtesy of: EXPLORE FLORIDA REALTY SERVICES LLC

  • 614 SAINT JOHNS CT #614, WINTER PARK, FL - MLS# O6410529

    WINTER PARK VILLAS CONDO - O6410529 - 614 SAINT JOHNS CT #614, WINTER PARK, FL 32792
    7 Days on yellowkey

    $1,750 | Condo | 2 beds | 2.0 baths

    Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area with small private courtyard. Cozy fireplace in the living room, lots of windows bring in the natural light of the Florida sunshine. Water/sewer is included in rent. Community pool and fitness room at the clubhouse only 2-3 minutes walking distance from the unit. Condo conveniently located near Colleges, Shopping and dining. Pets welcomed! (some restrictions apply)

    Contact Yellowkey Agent

    Listing is courtesy of: JEXOR LLC





Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.