Multiple Cities, Zip Codes, Addresses, Streets, Neighborhoods, MLS IDs
(separate each with the word OR)
Ex.Miami OR Coral Springs OR Boca Raton33319 OR 33321 OR 33467
Find Winter Park Real Estate for Rent by clicking on the relevant neighborhood.
View all Winter Park Real Estate for Rent
HIDDEN OAKS CONDO PH 11 - S5150258 - 3220 OAK LAWN PLACE PL #210, WINTER PARK, FL 32792 Just Added on 06/29/2026 11:29AM
$1,900 | Townhouse | 3 beds | 2.5 baths
This beautiful corner-unit townhouse offers comfort, space, and convenience in a highly desirable location. This home features 3 bedrooms and 2.5 bathrooms, providing plenty of space for families and professionals. The kitchen flows seamlessly into the living, dining áreas and private patio offering a practical design for everyday living. All bedrooms are located upstairs for added privacy, including a comfortable primary suite with its own private bathroom.Conveniently situated near shopping, dining, schools, colleges and roadways, this property offers both comfort and accessibility to everything you need while still providing a peaceful residential setting.
Listing is courtesy of: AGENT TRUST REALTY CORPORATION
WRENWOOD CONDO - O6420610 - 4812 TANGERINE AVE #4812, WINTER PARK, FL 32792 Just Added on 06/29/2026 8:25AM
$1,700 | Half Duplex | 2 beds | 2.0 baths | 3 car
Enjoy comfortable living in this well-maintained condo in a highly desirable Winter Park location. The home offers 2 spacious bedrooms and 2 full bathrooms, making it a great fit for families, professionals, or roommates. The bright open living and dining area creates a welcoming space for relaxing or entertaining. The kitchen includes all appliances, plus a washer and dryer for added convenience. Water is included in the rent, adding extra value. Both bedrooms offer generous space, natural light, and ample closet storage. The thoughtful layout provides privacy between the bedrooms, which is ideal for remote work or shared living. Located near Full Sail University, UCF, major highways, shopping, and everyday conveniences, the condo also offers easy access to Downtown Orlando. Residents can enjoy a community pool and fitness center in a quiet, private community. This property combines comfort, convenience, and a great location. It is an excellent rental opportunity in Winter Park.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC
VISTAS AT LAKE HOWELL - O6420636 - 2529 GALLIANO CIR, WINTER PARK, FL 32792 1 Day on yellowkey
$2,350 | Townhouse | 3 beds | 2.5 baths | 1 gar
Fantastic end corner unit with Seminole County Winter Park address. Gated community, 3/2.5 - 2 story townhome with open floor plan. Very convenient location just off Semoran Blvd, with Walmart super center, Publix and abundant of shopping and dining facilities nearby.
Listing is courtesy of: HONEST REAL ESTATE COMPANY
- O6416050 - 301 S CAPEN AVE, WINTER PARK, FL 32789 3 Days on yellowkey
$2,500 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue. Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage. Down the hall, you'll find three bedrooms with brand-new carpeting and easy access to the spacious backyard, offering plenty of room to relax or entertain outdoors.
Listing is courtesy of: CORCORAN PREMIER REALTY
AUTRYS PARK - WINTER PARK, FL 32789 3 Days on yellowkey
$7,500 | Single Family Home | 4 beds | 4.0 baths | 2 gar
Virtually Staged. Brand-New Luxury Home for Lease in Winter Park's Most Walkable Neighborhood Live in one of Central Florida's most desirable communities without compromising on space, style, or location. This brand-new, never-lived-in home by Nautilus Homes offers 4 bedrooms, 4 full bathrooms, a private office, and over 3,000 square feet of refined living, all in the heart of Winter Park, steps from everything that makes this city special. The moment you walk in, the difference is obvious. Crème Brûlée wide-plank wood flooring flows throughout, setting a warm, elevated tone that carries into every room. The open-concept living area is anchored by a built-in wine and coffee bar, perfect for morning routines and evening wind-downs alike. The chef's kitchen is the heart of the home, featuring custom ceiling-height cabinetry, a handcrafted wood range hood, and high-end finishes designed for serious cooking and effortless entertaining. Just off the kitchen, a beautifully appointed butler's pantry finished in statement Kit-Kat tile connects seamlessly to the formal dining room, a layout that makes hosting feel natural, not stressful. The floor plan gives everyone their own space. A private office and a full en-suite bedroom on the main level offer flexibility for working from home, hosting guests, or accommodating multigenerational living. Upstairs, three additional bedroom suites each feature walk-in closets and their own beautifully finished bathrooms, no sharing, no compromising. The primary suite is in a category of its own. A spa-inspired bathroom with a freestanding soaking tub, an oversized 9-foot walk-in shower with dual sprayers, a frameless glass enclosure, and sleek linear drainage make every morning feel intentional. The walk-in closet is generously sized and thoughtfully designed. Additional features include a 2-car attached garage, central air and heating, an irrigation system, wood flooring throughout, and electric dryer hookup, everything you'd expect in a home at this level, with nothing left out. Outside, you're minutes from Park Avenue, Winter Park Village, East End Market, and a tight-knit community known for tree-lined streets, top-rated schools, and a pace of life that feels a world away from the rest of Orlando. This is the rare rental that actually lives up to the photos. Reach out today, homes like this don't stay available long.
Listing is courtesy of: REAL BROKER, LLC
CONWILL ESTATES - O6420234 - 1791 SPRUCE AVE, WINTER PARK, FL 32789 3 Days on yellowkey
$4,900 | Single Family Home | 3 beds | 2.0 baths
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 storage. The spacious Florida room overlooks a private backyard complete with a sparkling pool, expansive deck, covered seating area, mature landscaping, and a fully fenced yard. Mango and lime trees, landscape lighting, and a powered storage shed with workbench make the outdoor space just as enjoyable as the inside. Additional features include hurricane impact windows, plantation shutters, updated lighting and ceiling fans, a Nest thermostat, surround sound, and a circular paver driveway. Ideally located just minutes from Park Avenue, Rollins College, the Winter Park Racquet Club, Winter Park Golf Club, Phelps Park, and the YMCA, with easy access to top rated schools, dining, shopping, and everything charming about Winter Park.
EASTBROOK SUB - O6420055 - 887 EASTBROOK BLVD, WINTER PARK, FL 32792 4 Days on yellowkey
$2,650 | Single Family Home | 4 beds | 2.0 baths
Come see this 4 bedroom 2 bath in the beautiful Winter Park neighborhood of Eastbrook. This home is completely move in ready with granite counter-tops and stainless steel appliances in the kitchen and new microwave. Large open kitchen/living room. Spacious bedrooms with lots of closets and storage space. Updated modern light fixtures and fans adorn the rooms throughout the home. Home is tiled and has new laminate throughout. Fenced backyard with huge screened in back porch.
Listing is courtesy of: ABSOLUTE REALTY GROUP, LLC
WINDWARD SQUARE SEC 2 - O6418670 - 2657 EXUMA WAY, WINTER PARK, FL 32792 4 Days on yellowkey
$2,400 | Townhouse | 3 beds | 2.0 baths
Freshly remodeled and move-in ready, this 3-bedroom, 2-bath townhome offers comfortable living in a highly desirable Winter Park location. The open-concept living and dining areas create a welcoming space for everyday living and entertaining, while the convenient pass-through window connects the kitchen and dining room for added functionality. The brand-new kitchen remodel features granite countertops and all-new stainless steel appliances. The spacious primary suite includes a walk-in closet and private en suite bath with a walk-in shower. Two additional bedrooms and a full bath offer ample room for everyone. Tile flooring throughout provides easy maintenance and durability. Enjoy time relaxing outdoors on the covered patio in the privacy of the fenced backyard. Additional recent updates include a new roof, all-new Low-E energy-efficient windows, and a new vanity, toilet, and faucets in the guest bath. Residents enjoy access to the community pool and clubhouse, along with a prime location close to shopping, dining, entertainment, and major roadways. With its combination of recent upgrades, community amenities, and sought-after Winter Park address, this is the perfect place to call home.
Listing is courtesy of: HAVEN PROPERTY GROUP LLC
TANGLEWOOD SEC 3 REP - O6419550 - 5117 LAKE HOWELL RD, WINTER PARK, FL 32792 5 Days on yellowkey
$2,395 | Single Family Home | 3 beds | 1.0 baths | 1 car
3/1, Carport, Single Family Home, Living Room, Dining Room, Eat in Kitchen, Stainless Steel Appliances Included: Stove, Microwave, Refrigerator, Dishwasher, Disposal, Inside Utility Room with Washer and Dryer Hookups, Laminate Wood Flooring & Ceramic Tile Throughout, Fenced Backyard, Pets Ok Upon Owner's Approval, NO SMOKING, Year Built: 1957/1300 Sqft.
Listing is courtesy of: LEGENDS REALTY
COLONIES - O6415308 - 7425 DANIEL WEBSTER DR #B11, WINTER PARK, FL 32792 6 Days on yellowkey
$1,295 | Condo | 1 beds | 1.0 baths
Discover this large first-level one-bedroom, one-bath condo in Winter Park. The unit features new cabinets and appliances, a remodeled bathroom, and new laminated flooring throughout. Enjoy a spacious bedroom with a bay window that brings in natural light, plus a covered tiled patio for outdoor seating. Washer and Dryer inside for convenience. The community offers a pool for residents. Everything is new and move-in ready; this condo combines recent updates with easy single-level access. Great location, ideal for Full Sail or UCF. Close to shopping and public transportation
Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE
LAUREL SPGS - O6419181 - 7522 LAUREL SPRINGS DR, WINTER PARK, FL 32792 6 Days on yellowkey
$2,200 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Located in the highly sought-after Winter Park High School district, this beautifully maintained 3-bedroom, 2-bath home in Laurel Springs provides comfort, space, and convenience. The bright and inviting living area features tile and an open, welcoming feel. Enjoy year-round indoor-outdoor living in the expansive 400+ sq. feet. enclosed patio overlooking a fully fenced backyard—perfect for entertaining, relaxing, or family gatherings. Ideally situated with easy access to shopping, dining, parks, and major highways. Move-in ready!!!!
Listing is courtesy of: JOY ESTATE ENTERPRISE INC
LAKE FOREST PARK S/20 LOT 26 BLK B - O6419042 - 2234 HOWARD DR, WINTER PARK, FL 32789 7 Days on yellowkey
$8,295 | Single Family Home | 4 beds | 5.5 baths | 2 gar
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 entertaining and casual gatherings. The gourmet kitchen is a chef's dream, complete with an enormous walk-in pantry, high-end appliances, and seamless flow into the dining area. Entertain in style with a wet bar and food service station, perfect for hosting elegant dinners or festive celebrations. Master Suite is an expansive sanctuary that features a spa-like bathroom equipped with a soaker tub, walk-in shower, His and Her vanities Step outside to your private heated lap pool, perfect for fitness or relaxation. The backyard retreat is surrounded by lush landscapingan ideal oasis for quiet relaxation or sunny Florida afternoons. A first-floor bedroom with en-suite bath adds convenience for guests or multi-generational living. Perfectly situated near Audubon Park and Baldwin Park, this home offers unbeatable access to top-rated schools, including Audubon Park K-8 & Winter Park H.S. Ideally situated near Downtown Orlando, Rollins College, hospitals, renowned restaurants, and boutique shopping, making it a prime location for those seeking convenience and accessibility. Explore numerous community parks, perfect for those who enjoy an active outdoor lifestyle. An area rich in culture with nearby museums to explore and learn. This is more than just a homeit's a lifestyle. Experience the best of Winter Park living: elegant, elevated, and effortlessly connected. Pets negotiable with owner approval. Additional fees may apply.
Listing is courtesy of: COLDWELL BANKER REALTY
WRENWOOD CONDO - O6415325 - 4796 TANGERINE AVE #4796, WINTER PARK, FL 32792 7 Days on yellowkey
$1,600 | Condo | 2 beds | 2.0 baths
Cute 2 bedroom, 2 bathroom, freshly painted condo in Winter Park. Amenities include a swimming pool, fitness center, clubhouse/conference room, well-maintained grounds, and ample parking. This property offers easy access to Full Sail University, University of Central Florida, Rollins College, Downtown Winter Park, Baldwin Park, and Downtown Orlando. Shopping, dining, entertainment, parks and grocery stores are all nearby. Major highways SR-417 and SR-408 are easily accessible. There is a washer and dryer in the condo and new carpet throughout bedrooms and main living areas. There is a screened in back patio with storage closet.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES
VILASA TWNHMS - O6418569 - 501 W CANTON AVE, WINTER PARK, FL 32789 10 Days on yellowkey
$6,500 | Townhouse | 3 beds | 2.5 baths | 2 gar
Look no further, this luxury Modern Townhome offers premium location just minutes from Park Avenue, restaurants, shopping, Hannibal Square, and Rollins College just to name a few! Through the front door you are met with 13-foot ceilings, Modern finishes, Pella double windows, and wood flooring throughout. The Chef’s gourmet kitchen is complete with high-end flat panel cabinetry, Quartz countertops, Wolf gas cooktop, and Subzero appliances! On the second floor there are three bedrooms, 2 full bathrooms, utility room and the spacious primary bedroom is equipped with an oversized walk-in closet, opulent tub, walk-in shower, and Quartz countertops. Schedule your private showing today!
WINTER WOODS UNIT 04 - S5152229 - 2028 SUSSEX RD, WINTER PARK, FL 32792 10 Days on yellowkey
$2,900 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome home to Winter Park living at its finest in this beautifully updated one-story home where comfort, convenience, and charm come together. From the moment you enter, you'll notice the bright, freshly painted interior, spacious layout, and modern touches throughout—including new updated bathrooms, landscaping enhancements and brand-new stainless-steel appliances. The attached two-car garage adds everyday ease, while the included washer and dryer. Step outside to your private backyard retreat, where a peaceful water view and inviting fire pit creates the perfect setting for morning coffee, weekend gatherings, or quiet evenings under the stars. Professional landscaping and pest control are also included, so you can spend less time on upkeep and more time enjoying your home. Ideally located near Downtown Winter Park, Park Avenue, local coffee shops, restaurants, grocery stores, entertainment, and daily conveniences, this home also offers quick access to Maitland, Casselberry, Orlando, I-4, and SR-417. Zoned for Seminole Country Schools. If you're searching for a stylish, low-maintenance rental in a prime location, this Winter Park home is ready to welcome you. Schedule your showing today!
Listing is courtesy of: CENTRAL FLORIDA REALTY MANAGEMENT LLC
LAKE KNOWLES TERRACE ADD 02 - O6413008 - 1540 ONECO AVE, WINTER PARK, FL 32789 10 Days on yellowkey
$2,500 | Single Family Home | 3 beds | 2.0 baths | 1 car
Nestled on a picturesque, tree-lined brick street, this charming 3-bedroom, 2-bath home offers an unbeatable location just minutes from Park Avenue, Rollins College, shopping, dining, and entertainment. Inside, you'll find a spacious floor plan featuring a formal living room, dining room, and family room, providing plenty of space for both relaxing and entertaining. The kitchen is equipped with all appliances and includes a breakfast bar along with a cozy eat-in dining area. Tile flooring runs throughout most of the home, with carpeting in one bedroom for added comfort. Additional features include an inside utility room with washer and dryer hookups, a large screened-in back porch perfect for enjoying Florida's beautiful weather, and a backyard storage shed for extra convenience. A two-car carport provides covered parking, and lawn care is included, making maintenance easy and worry-free.. All of our residents are enrolled in the Resident Benefits Package (RBP) for $39.95/month, which includes renters insurance, *RentSpree applications will not be accepted. Residents are enrolled in the Resident Benefits Package (RBP) for $39.95/month. More details upon application. This home combines charm, space, and convenience in one of the area's most desirable locations. Schedule your showing today!
Listing is courtesy of: WATSON REALTY CORP