Winter Park Apartments for Rent - 80 rentals

Remarks: FULLY FURNISHED and move in ready elegant home.A rare find in Winter Park. 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 picturesque street, the property boasts inviting curb appeal with mature landscaping and a welcoming entrance. Inside, thoughtfully designed living spaces feature abundant natural light, an open and functional layout, and seamless flow ideal for both everyday living and entertaining. The private backyard provides a serene retreat with ample space for relaxing or hosting gatherings. Step outside to your fully fenced backyard, complete with a private hot tub and spacious patio, ideal for relaxing evenings or casual get togethers. With no pool to maintain, you'll enjoy low maintenance outdoor living in a peaceful setting.1 time cleaning per month and wifi included. Located near top-rated schools, parks, and cultural attractions, 2075 Jewel Avenue presents a rare opportunity to enjoy refined living in one of Florida’s most prestigious neighborhoods. Mid term lease available.

Listing is courtesy of: URBANISTA BROKERS (407-619-7272)

Listing Agent: Paul Jimenez (407-276-3516)

Remarks: 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 (321-754-9131)

Listing Agent: Liu Zhang (917-892-2868)

Remarks: 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 (855-450-0442)

Listing Agent: Christina Fata (407-917-8946)

Remarks: This first floor, 2 bedroom, 1 bathroom condo is located in the heart of Winter Park. Enjoy all of Downtown Winter Park, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include an open main living area, lovely kitchen with granite countertops and stainless steel appliances, spacious bedrooms, and upgraded bathroom. This boutique community includes an on-site laundry facility. Pets under 40 lbs may be considered. Photos shown are of a comparable unit with a similar floor plan and finishes; minor variations in layout, fixtures, colors, views, and other features may exist. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.

Listing is courtesy of: REAL PROPERTY MANAGEMENT AND REALTY (407-897-3366)

Listing Agent: Matthew Kirsch (407-897-3366)

Remarks: Welcome to Grayson Square in Winter Park. This beautifully maintained 3-bedroom, 2.5-bath townhome is located in one of the area’s newer gated communities and shows like new throughout. Exceptionally clean and well cared for, this home is truly move-in ready. The open-concept living and dining area offers a comfortable layout for both everyday living and entertaining. The covered lanai overlooks a peaceful pond, providing a relaxing outdoor space with a serene view. The kitchen features stainless steel appliances, quartz countertops, ample cabinetry, and generous storage. Upstairs, the spacious owner’s suite includes a walk-in closet and a private bathroom with dual sinks, quartz countertops, and a glass-enclosed shower. The second full bathroom includes a tub with shower combination. A washer and dryer are included for added convenience. Residents enjoy gated entry, a resort-style pool, and cabana amenities. Rent includes 1GB fiber-optic internet service along with 75 streaming cable and music channels. Conveniently located just minutes from Downtown Winter Park and Park Avenue, with easy access to SR 436, SR 434, and SR 417. Close to shopping, dining, and everyday essentials including Publix, Walmart, and Starbucks. Zoned for highly regarded Seminole County schools.HABLO ESPANOL.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Denise Del Castillo (321-960-3110)

Remarks: 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 (407-673-1400)

Listing Agent: Courtney Davis (407-493-8329)

Remarks: 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 (407-928-3894)

Listing Agent: Jerry Agan (678-873-4463)

Remarks: 3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and lawn service included. *Bonus Amenity Included* -All residents are enrolled in the Resident Benefits Package (RBP) for $49.95/month which includes liability insurance, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, HVAC air filter delivery (for applicable properties), move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, on-demand pest control, and much more! More details upon application.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Shawn Beard (407-571-1401)

Remarks: 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!

Listing is courtesy of: TRANSCEND REALTY (407-518-7653)

Listing Agent: Jacob Hara (407-933-5478)

Remarks: Enjoy comfortable Winter Park living in this freshly painted 3-bedroom, 2.5-bath townhome located in the gated community of Grayson Square. Thoughtfully designed for everyday living, this home features a spacious open-concept living and dining area, perfect for entertaining, with direct access to a covered lanai for relaxing outdoors. The kitchen offers stainless steel appliances, quartz countertops, and ample cabinet space for storage and functionality. Upstairs, the owner’s suite includes a large walk-in closet and a private bathroom with dual sinks, quartz counters, and a glass-enclosed shower. A washer and dryer are also included for added convenience. Additional highlights include a two-car garage with epoxy floors and ceramic tile flooring throughout the main living areas, providing both style and easy maintenance. Residents of Grayson Square enjoy gated access, a community pool with cabana, and 1GB high-speed fiber optic internet included in the rent, along with 75 streaming cable and music channels. Ideally located near downtown Winter Park, this home offers easy access to Howell Branch Road, 436, 434, and 417. Starbucks, Publix, and Walmart are just minutes away, while the shopping and dining of Park Avenue are approximately 15 minutes away. Top-rated Seminole County schools are also nearby. A wonderful opportunity to lease a well-maintained home in a convenient Winter Park location. ¡Hablo Español!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Denise Del Castillo (321-960-3110)

Remarks: 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 areas, updated kitchen with granite countertops and modern cabinetry, plus updated bathrooms with clean finishes. The bonus room offers flexibility for a home office, gym, playroom, or additional living space. Major updates include roof replaced in 2018, fully paid solar panels installed in 2020, water heater 2019, and A/C replaced in 2013. Conveniently located near Park Avenue, Rollins College, Full Sail University, University of Central Florida, shopping, dining, and major highways. First month’s rent, last month’s rent, and security deposit required prior to move in. Background and credit check required through RentSpree at tenant expense ($50 x adult over 18 years old). Preferred credit score 550+. No prior evictions. Pet restrictions apply.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Alexa Monasterio Flores (786-915-9294)

Remarks: 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 (407-333-1010)

Listing Agent: Tina Lopez (407-333-1010)

Remarks: 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.

Listing is courtesy of: DOUGLAS EDMUND REAL ESTATE LLC (407-853-4402)

Listing Agent: Yuly Rodriguez (407-879-0720)

Remarks: This 2-bedroom, 1-bathroom duplex, is perfectly located in the heart of Winter Park! This home offers the ideal blend of comfort, convenience, and tranquil living. With an open-concept living and dining area that makes entertaining effortless. The kitchen features ample storage and counter space, perfect for meal prep and daily use. Step outside to your private outdoor space, ideal for relaxing or hosting guests. Conveniently located just minutes from top-rated schools, shopping, dining, and major highways, this home offers both serenity and accessibility. Pets Allowed! $250.00 Non-Refundable Pet Fee each Pet Tenant Liability Insurance **Required*

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Carissa Lawhun (407-207-2220)

Remarks: 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!

Listing is courtesy of: EXPLORE FLORIDA REALTY SERVICES LLC (407-982-9709)

Listing Agent: Shannon Lee (407-982-9709)

Remarks: Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix, Trader Joe's, Regal Movie Theater, and a variety of restaurants and bars. Join this vibrant community and make this beautiful condo your new investment property or dream home!

Listing is courtesy of: FLORIDA DREAMS REALTY GRP INC (407-654-9992)

Listing Agent: Adriana Montes (407-654-9992)

Remarks: LOCATION! LOCATION! LOCATION! Home well positioned on large 0.28 acre lot in 32789. Gorgeous two bedroom home right in the heart of Winter Park , that just had a new roof put on.. At just a ten minute drive from Orlando, this home is in a very convenient location for anyone who wants to be in and out of the city whenever they'd like. Beautiful interior, with original wood flooring throughout. Tile in the spacious open kitchen that opens into the living room, giving this home a wide-open layout. Enjoy, the peaceful, secluded feeling when lounging on the deck in the generous backyard during warm summer nights. Large, fenced backyard. Lake Killarney access for kayaking and canoeing.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Vincent Paige, Pa (407-256-8190)

Remarks: Stunning newer-construction luxury home in Winter Park offering 5 bedrooms, 4 baths, and 4,100 sq ft of modern living. Sleek architectural lines, abundant natural light, and seamless indoor–outdoor flow define this exceptional residence. The chef’s kitchen features premium stainless steel appliances, breakfast bar, custom cabinetry, and a large walk-in pantry. The spacious living area includes a reclaimed Chicago brick fireplace and full-length sliders opening to a resort-style lanai with summer kitchen, wood ceiling, and recessed lighting. Step outside to a private backyard oasis with a sparkling pool, outdoor kitchen area, and no rear neighbors—perfect for entertaining. The first-floor primary suite offers complete privacy with a spa-inspired bath, soaking tub, walk-in shower, and dream closet. The main level also includes a private office, full bath, dining room, laundry room, and generous living spaces. Upstairs features a large loft, rumpus room, four additional bedrooms, and two beautifully designed baths. The oversized two-car garage provides high ceilings, storage, and a flex space ideal for bikes, fitness, or workshop use. Located minutes from Park Avenue dining, shopping, and entertainment, this home delivers luxury, comfort, and an unbeatable Winter Park lifestyle. Professionally managed with exceptional service.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Tab Bish Llc (855-450-0442)

Remarks: 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 (407-380-2800)

Listing Agent: Celimar Sierra, Llc (407-731-2678)

Remarks: Experience maintenance-free living in this spacious 2-bedroom, 2-bath condominium offering 1,529 square feet in the gated Park West community in the heart of Winter Park. Located on the top floor, this spacious residence features vaulted ceilings, hardwood flooring, quartz countertops, stainless steel appliances, walk-in closets, a soaking tub, a stacking washer and dryer, and charming Juliet balconies. Residents enjoy exceptional amenities, including a community pool, tennis courts, clubhouse, and an assigned garage parking space. Water service is included in the rent. Park West is across the street from the weekly Winter Park Farmers' Market, and one block from Park Avenue; you'll have easy access to boutique shopping, highly renowned restaurants, the SunRail station, and everything that downtown Winter Park offers. Cats will be considered on a case by case basis with a non-refundable pet fee and monthly pet rent. Prospective tenants are subject to the Park West Condominium Association approval process and associated application fee.

Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)

Listing Agent: Anthony Consalvo (407-599-7070)