Windermere Single Family Homes For Rent - 46 homes

Remarks: Great House, Great Location! 4 beds and 3.5 baths just a few years old around the corner from the Lakeside Village Center in Windermere. This home is right across the street from the playground and pool center. With decorative pavers for the driveway, huge covered front porch. Choose to run across the street to take a dip in the gorgeous community pool, or sit on the front porch watching your friends and neighbors go by. For more privacy, enjoy the huge covered and screened-in lanai in the back with a back yard having partial block privacy wall on back and one side. Inside the home has a first floor bedroom and full bath, open den/office/formal dining, back study room or office with separate glass door to the back lanai and half bath powder room. The main great room is open living, kitchen, and dinette with French doors and side lights to outside. The kitchen has huge island with sink and breakfast bar, darker cabinets with black granite and crown molding. All stainless steel appliances. The master bedroom upstairs has a walk-in closet, large master bath with Separate vanities. One on each side of the garden tub and a separate walk in shower and a separate toilet room. Bedrooms 3 and 4 are separated by the hall bath, and laundry room with washer and dryer are near the stairs. The garage has a speckled painted floor. The Westside Village community has a nice playground next to the resort style pool and plenty of walking trails around the ponds next to the forest. A great location near the heart of Windermere with A-rated schools and shopping around the corner. You will love calling this place home. Please Email for more info or set up showing. information deemed reliable but not guaranteed. please verify

Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)

Listing Agent: Bryce Rysewyk (407-340-1754)

Remarks: Rare Newer Construction (2017) Windermere Pool Home located in close proximity to Downtown Windermere. This is a 2 Story home with tiled roof and so many upgrades and amenities. Beautiful Open floorplan with all of the upgrades. Through the large Sliding Glass doors, you flow into a fully covered Lanai and into the stunning brick paved pool area w/ Jacuzzi and the Scenic Landscaped Lot. This is an Entertainer's Dream Home. Equipped with Outdoor speakers, Outdoor Grill, Exhaust, Refrigerator, Stove, pool Bath and Lanai. The Kitchen layout adds to this with a large Island to gather and entertain guest. The Wine Cooler addition is a plus. Additional Classy Spiral staircase adds additional access to the upstairs Loft style Family Areas. This home was built with an exceptionally large Master bedroom extension as well as an oversized laundry room. More than adequate closet space. Three Car Garage. The front offers a covered patio for sitting during the cool Florida evenings. Located in Close Proximity to all local Public and Private schools and Shopping and Restaurants, Publix etc. Pets are Negotiable and a multi-year lease is considered. Tenants will handle Lawn and Maintenance, or it can be added as a convenience. This estate style subdivision is like no other with beautiful grounds, Huge fully fenced back yard. High ceilings show off the cutting-edge architecture of the floorplan. Exceptionally rated schools - Windermere Elementary, Bridgewater Middle School and Windermere HS. This one should lease very quickly.

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Corey Cannon (407-615-0215)

Remarks: Beautifully maintained 4BR/3BA pool home in gated Glenmuir, Windermere. Open floor plan with high ceilings, formal dining, and spacious family room. Kitchen with breakfast nook overlooks screened pool/lanai. Primary suite features dual closets, spa bath, and pool access. Enjoy a private 0.25-acre lot in a tree-lined community. Glenmuir provides a community park with playground, basketball courts, soccer field, pavilion, and picnic areas. Conveniently located near Winter Garden Village, Lakeside Village, and Walt Disney World, the neighborhood is also zoned for top-rated Orange County schools and less than a mile from Windermere Preparatory School.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: David Sanchez (321-262-2322)

Remarks: Welcome to your private luxury retreat in the exclusive gated community of Casabella in Windermere. This exceptional fully furnished estate offers over 5,400 square feet of thoughtfully designed living space, featuring 5 bedrooms, 5.5 bathrooms, and a 3-car garage—perfectly blending elegance, comfort, and functionality. From the moment you arrive, the circular driveway and lush, manicured landscaping set the tone for what awaits inside. Step through the doors to discover a light-filled interior with refined finishes, expansive living areas, and designer furnishings curated for both everyday living and effortless entertaining. The home flows seamlessly from indoors to out, where your private backyard oasis takes center stage. Enjoy a resort-style pool and spa overlooking a tranquil pond, surrounded by tropical palms and Florida-native landscaping. Whether you’re hosting under the stars, relaxing in the spa, or gathering around the fire pit by the water, this space was designed for unforgettable moments. The fully fenced backyard provides both privacy and beauty, creating a peaceful retreat that feels worlds away—yet is just minutes from everything. Located in the highly sought-after town of Windermere, you’ll enjoy a rare combination of privacy, prestige, and convenience, with close proximity to top-rated schools, upscale dining, shopping, and Central Florida’s premier attractions. For added ease, lawn care and pool maintenance are included, allowing you to focus on enjoying the lifestyle this home offers—without the upkeep. This is a rare opportunity to lease a turnkey luxury home in one of Central Florida’s most desirable communities. Schedule your private showing today and experience elevated living at its finest. Pet Policy --One Dog of 35lb or less (full grown size) - NO AGGRESSIVE BREEDS! Pet insurance is required as well as current vet records. A non-refundable pet fee and additional rent is required for an approve pet . Failure to report any animal intended for residency will invalidate your application and immediately terminate your lease if you are selected. YOU MUST TOUR THE PROPERTY PRIOR TO SUBMITTING AN APPLICATION. Application Process: You will be required to submit the following when you fill out your application: Driver's License/State ID, Income Verification, and pictures, if any, of your pet. This must be done when you apply in order to proceed with your application. APPLICATION FEES ARE NON-REFUNDABLE AND APPLY TO EVERYONE 18+ YEARS OR OLDER. We check: Credit (rental collections and utility collections are red flags) Rental history Employment Background (extent determined by HOA requirements) Gross income must meet or exceed 3 times the monthly rent to qualify for the property you are interested in. Example-Applicant must be able to prove $3000 gross income (verifiable) in order to qualify for home that rents for $1000 a month. What is provable income? A copy of your last pay stub or a letter from your employer will help in determining your income. Sometimes copies of your bank statement or your tax return, W2 forms or 1099 forms are necessary as well. Types of income include, Child Support, Spousal Support, SSI, Retirement and/or Disability, Wages, Parental Support and Student Financial Aid. ALL APPLICATIONS ARE SUBJECT TO OWNER APPROVAL!

Listing is courtesy of: RIGHTHOUSE REALTY LLC (407-216-8788)

Listing Agent: Tim Schmidt (407-216-8788)

Remarks: Beautiful 4-bedroom 2.5 bath home located in the desirable Lakes of Windermere community. This two-story corner lot home has everything you can ask for, formal living and dining rooms, kitchen with granite countertops, stainless steel appliances, and a breakfast bar that opens to a large family room, on the first floor you also have a massive master bedroom suite, with a large closet and the bathroom with double sinks, garden tub, and separate shower. On the second floor, you have 3 bedrooms and a shared bathroom. Afterwork you can relax on the front porch or on the screened back lanai. The community has lots of amenities pool, a tennis court, walking trails, and a dock. A-rated schools. Close to shopping, amusement parks, and an easy commute. +++++++ Evaluation criteria for prospective tenants: - No Evictions - No Sex Offenders - Credit score minimum 630 - Income to rent 3 times minimum - One small pet may be considered, nonaggressive breeds only. ***Some photos are virtually staged.

Listing is courtesy of: SHINING OAK REALTY (407-399-2298)

Listing Agent: Paul Moscoso (321-210-2456)

Remarks: Be the First to Call This Home Yours! Brand New Luxurious 2025! Move-In Ready! Pet Friendly! 2-Car Garage! Smart Home! Stunning 6 Bedrooms, Loft, Bonus Room, Stylish Upgrades! Internet & WiFi Included! Step into luxurious, modern living in this expansive 6-bedroom, 3.5-bath, two-story smart home featuring a bright, open-concept layout that seamlessly connects the gourmet kitchen, family room, and dining area. The chef-inspired kitchen boasts a large island, quartz countertops, stainless steel appliances—including a gas cooktop, built-in microwave and oven, bottom-freezer refrigerator, and sleek range hood—plus a spacious walk-in pantry and recessed lighting for a polished, contemporary look. The first-floor master suite is a private retreat with double doors opening to a spa-inspired ensuite featuring a soaking tub, oversized walk-in shower, and dual-sink vanity with ample cabinet space. Upstairs, a versatile loft and bonus room offer endless possibilities for a game room, home office, or media space. Additional bedrooms are generously sized, and all baths reflect the home’s sophisticated style. Additional highlights include a striking metal-frame staircase, durable first-floor vinyl, plush second-floor carpet, a thoughtfully designed laundry with cabinets, sink, and washer/dryer, a 2-car garage, and smart home features including wired ceilings with built-in speakers for seamless entertainment. Enjoy vibrant community amenities including pickleball courts and a playground, all in the highly desirable Windermere area. Move-in ready, luxurious, smart, and perfect for modern family living—schedule your tour today!

Listing is courtesy of: RENT A FLORIDA HOME (863-232-6262)

Listing Agent: Katrina Anarumo (863-232-6262)

Remarks: Welcome home! This beautiful 3-bedroom, 2-bath home is available for immediate move-in. Conveniently located in the desirable Silver Woods community in Windermere, this property features a comfortable layout with well-proportioned bedrooms and bathrooms, plus a spacious kitchen with plenty of counter and cabinet space. The home offers bright living areas and a functional floor plan perfect for everyday living. Lawn care is included with rent for added convenience. Residents of Silver Woods enjoy community amenities including tennis courts and recreational areas, all while being just minutes from shopping, dining, entertainment, and major attractions. Act now—this one won’t last long! All applicants are required to complete a credit and background check. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents may opt out of the master policy by providing proof of their own policy that meets minimum requirements.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Steven Simpson (407-545-2594)

Remarks: VACANT! Great location! Great Home! Move into this Great home inside the lovely SUMMERPORT/WINDERMERE community. This house is full of upgrades and is an Energy Star certified home. Downstairs it has all tiled floors and new laminate. Kitchen has all full appliances and granite countertops. You can also enjoy Disney fireworks at night. Upstairs there is a large master bedroom, and three bedrooms. Master bathroom has double sink, granite countertop, garden tub and a separate large shower room. Laundry room is located on second floor with a large space for storage. A-rated schools and Shopping Center with Publix Supermarket is just at the corner. Easy commute to most parts of Orlando. Basic tenant requirements: 675+ credit score, no BAD RENTAL history, no BAD history, income 3x monthly rent as a household.

Listing is courtesy of: CINO INTERNATIONAL INC (407-354-3318)

Listing Agent: Daniel Zheng (407-683-1881)

Remarks: Welcome home to this beautifully maintained property in Windermere’s sought-after Summerport community. Enjoy a chef-inspired kitchen complete with solid countertops, updated stainless steel appliances, and a gas range—perfect for everyday living and entertaining. New interior paint, stylish flooring throughout, and upgraded lighting and bathroom fixtures make this home the perfect rental! Conveniently zoned for Windermere High School

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Alex Sadowski (407-405-1079)

Remarks: Live in one of the most sought after locations of Windermere! Welcome to 9313 Palm Tree Drive, located just minutes from Disney, Dr. Phillips, and Restaurant Row without the traffic and chaos. Located in the Silver Woods community off Apopka Vineland Rd, this 3 bedroom, 2 bath recently updated home is the perfect spot as your new home! Inside, you’ll find updated quartz countertops, newer appliances, wood look plank tile flooring throughout the bedrooms, and spacious closets in every room. Both bathrooms have been recently updated with new countertops and sinks for a clean, modern feel. Step outside to a fully fenced backyard with plenty of space to relax, entertain, or enjoy the outdoors! Rent includes Pest Control and Lawn Maintenance! Homes in this location don’t come up often for rent. If you’re looking for convenience, location, and a clean well kept home, this is it. Inquire today!

Listing is courtesy of: FHG REALTY, LLC (407-505-7600)

Listing Agent: Jeff Inman (407-505-7600)

Remarks: Spacious 6-bedroom, 3.5-bath unfurnished home offering 3,841 sq ft in the desirable Windermere Sound community. This well-designed floor plan features a downstairs primary bedroom, a large upstairs loft, generously sized bedrooms with walk-in closets, an office area and an expansive kitchen complete with a walk-in butler pantry and ample cabinet space—perfect for entertaining and everyday living. The home features a screened in lanai, fenced in backyard and 3-car garage. Conveniently located near shopping, dining, and major attractions. Move-in ready and available now!

Listing is courtesy of: PABLA PROPERTIES (407-967-2757)

Listing Agent: Sunny Pabla (407-967-2757)

Remarks: Located in the gated community, The Preserve at Lakes of Windermere, this 4 bedroom 3 bath home is available now to lease! Featuring laminate floors, plenty of storage, open porches, and an expansive kitchen with stainless steel appliances that overlooks the living room. The community features a large pool and playground. Close proximity to Disney and easy access to shopping, major highways and great schools.

Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)

Listing Agent: Kevin Sullivan (321-663-3457)

Remarks: Come make this Beautiful and scenic house your new home. One of the great communities in Windermere. Top school district. Must see to appreciate.

Listing is courtesy of: VINTAGE REALTY GROUP LLC (407-217-5458)

Listing Agent: Scott Howard (305-934-7727)

Remarks: Welcome home! This fantastic 2-bedroom, 2-bath home is available for immediate move-in! Located conveniently in the desirable community of Summerport, this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act now! This one won't last long! All applicants are required to do a credit and background check. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Steven Simpson (407-545-2594)

Remarks: POOL HOME!!! WITH MOTHER IN LAW SUIT!!! 5 BEDROOMS 4 FULL BATHS!!! MAN-GATED COMMUNITY IN WINDERMERE!!! Stunning Windermere home at 1351 Glenwick Dr! Spacious open floor plan, modern kitchen, and elegant finishes throughout. Perfect for entertaining or relaxing in the private backyard. Close to top schools, shopping, and dining. A must-see blend of luxury, comfort, and location!

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

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

Remarks: Ready for immediate occupancy. No HOA. Welcome to Sunrise on The Lake, an exceptional, fully remodeled one-story retreat in the heart of downtown Windermere with stunning views over Lake Bessie. Wake up to breathtaking sunrises and, on clear evenings, enjoy the rare treat of watching rocket launches from Cape Canaveral right your home. Inside, every detail feels elevated, solid wood floors, level 5 finished walls and ceilings, and a cozy gas fireplace create a refined, inviting atmosphere. The elegant dining room features a marble top credenza, perfect for hosting. The chef’s kitchen is fully equipped with leathered stone countertops, Samsung stainless steel appliances, a Bosch dishwasher, gas range, and a beautiful porcelain farmhouse sink. The Florida room opens to a private half-acre backyard oasis. The primary suite offers three closets, dual vanities, and a sleek glass shower. A secondary bedroom overlooks the lake and sits next to a full adjacent bath, ideal for guests or a home office with a view. Step outside and prepare to be impressed, an inground heated saltwater pool and spa with massaging jets, two gas fire bowls, water features, a louvered pergola for outdoor dining and entertaining, plus an outdoor shower. The property also includes a four-car garage for a workshop/storage/car collection, fenced backyard, whole-house generator, and newer major systems (including plumbing, AC, and ductwork). Just a short distance to the Windermere business district’s restaurants and shops. Enjoy easy access to the Lake Bessie and Lake Butler boat ramps, weekly farmers market, monthly food truck night, top-rated schools, and you’re only about 15 minutes from the major theme parks. Make this home yours and be sure to click the virtual tour links!

Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)

Listing Agent: Simon Simaan (407-558-1396)

Remarks: Welcome home to your Windermere Isle Mediterranean estate. From the minute you arrive at this move in ready, model like home, you are greeted by a cozy hand cut stone façade & barrel tile roof reminiscent of rich Tuscan architecture. The brick paver driveway leads you to the inviting front porch & through the leaded glass front door to an open floor plan featuring your formal living & dining rooms. The spacious foyer opens up to the great room & gourmet kitchen with breathtaking views of your screened custom pool & covered lanai. Your chef's dream come true gourmet kitchen is well equipped with a large Quartz cooking island with upgraded wainscoting, pendant lights, level 3 kitchen cabinets with crown molding & upgraded handles, dual built-in ovens with a smart convection oven, a natural gas cooktop with a microwave & hood vented to the outside, glass tile backsplash, Whirlpool Gold Series stainless steel appliances and a walk-in pantry. The adjacent breakfast nook & great room open up to the extended 31'x9' covered lanai, making this the ideal area to entertain your guests. Speaking of entertaining, no expense was spared on your privately fenced custom resort style Dreamscapes gas heated, salt water pool & spa, featuring a water fall with 2 cascading bronzed bowls over sparkling Anthracite tile and a sunshelf with bubbler; your ideal lush oasis to escape to as you enjoy your favorite libation after a long day. The spacious rich Travertine pool deck offers plenty of sun bathing options & leads to the bar featuring a stainless steel Paradise Grill ready to cook up your culinary creations. A guest bedroom is conveniently located on the first floor with a walk-in closet & adjacent en-suite bath with tub and shower. The stairs feature an upgraded wrought iron railing and lead you to the 2nd floor bonus room featuring a built in library bookshelf & desk with rolling ladder; the ideal room that can easily accommodate a home theatre, a fitness or yoga studio, home office, game room or your desired flex space. The serene master retreat is privately located in a split floor plan configuration and features Cortec luxury vinyl planking, 2 walk-in closets & a spacious master bath with dual Viatera Quartz vanities with upgraded tile motif wall accents, separate shower & bathroom stalls & a garden tub. The Disney fireworks are just a glimpse away through your master bedroom window. The remaining bedrooms all feature durable Cortec luxury vinyl planking and walk-in closets with the 4th and 5th bedroom sharing a Jack and Jill bath. Peace of mind & energy efficient living at its best with 2 Ring doorbells, 2 Nest smart thermostats, iAquaLink pool automation with mood lighting, upgraded wood plank look ceramic tile floors, barrel tile roof, double pane low E windows throughout, tankless water heater, Tesla car charger in the 3 car garage, and R-38 blown insulation & rigid foam filled concrete block walls; leading to an HERS 60 energy efficiency rating for this Beazer built Sequoia II home. Windermere Isle also features a community pool and cabana, play ground, pond front park with bbq grills with the HOA taking care of the lawn care & fertilization. All this in a great location with excellent schools & just minutes from Disney, Historic Winter Garden, major highways, the Cinepolis Luxury Cinema, shopping at Hamlin Town Center or Winter Garden Village or to visit one of the many close by restaurants that are sure to curb any craving that you may have.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: T.J. O'Donnell (317-246-8190)

Remarks: Welcome to this spacious, fully furnished, 4-bedroom, 4.5-bathroom home nestled within a desirable gated golf community of Keene's Pointe. Thoughtfully designed for comfort and functionality, this impressive residence features a first-floor primary suite offering privacy and convenience, complete with a well-appointed ensuite bath. The home boasts generous living areas filled with natural light, creating an inviting atmosphere perfect for both everyday living and entertaining. A dedicated office space provides the ideal setup for working from home or managing daily tasks with ease. Step outside to your private backyard retreat featuring a sparkling pool, hot tub, and patio area—perfect for relaxing weekends or hosting gatherings. A 2-car garage adds convenience and additional storage space. Not to mention pool service and lawncare is included! With ample room for family and guests, plus the security and exclusivity of a gated community, this exceptional home offers the perfect blend of space, comfort, and lifestyle. All residents are enrolled in a Resident Benefit Package for $39.95/ month. More details upon application. RentSpree applications will not be accepted.

Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)

Listing Agent: Rose Sepulveda-Morales (407-973-0641)

Remarks: AVAILABLE MAY 2026! Spacious 4-bedroom, 2.5-bath home in the desirable Lakes of Windermere community. This well-designed floor plan features all bedrooms upstairs, with the main floor offering a large living room, formal dining room, office/reading room, and a convenient half bath for guests. The primary suite includes dual vanities, a garden tub, and two large walk-in closets. The kitchen is perfect for cooking and entertaining with ample cabinet and counter space, plus an island with bar seating, and it opens to the living room for a comfortable open feel. Enjoy relaxing evenings on the paved, screened patio overlooking a peaceful pond. Community amenities include pool, tennis and basketball courts, playgrounds, Lake Sawyer pier, Pine Trees Park gazebo, and nearby outdoor recreation areas.

Listing is courtesy of: ICON REALTY ASSOCIATES INC (321-303-5851)

Listing Agent: Silvia Odebrecht (917-374-9711)

Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Discover this newly updated 4 bed/2.5 bath single house located in the highly sought-after Windermere Trail community at Windermere. This cute house has a very spacious front porch for rocking chairs and morning coffee. Inside this airy and high-ceiling home, the newer luxury vinyl flooring on the stairs and the whole 2nd floor boasts upscale appearance and easy cleaning. Upon the entry a huge living room with flooding natural light through multiple windows welcomes family and friends. The living room opens to a gourmet kitchen with granite counter top, 42” maple cabinetry and stainless steel appliances. Next to the kitchen, a separate dining room with abundant light is perfect for gatherings formal or casual. Ascending the elegant and newer vinyl stairs you reach the 2nd floor bedrooms and the loft. The loft is perfect as a great room for TV, games or even study. The master bedroom is separated from other 3 bedrooms. The spacious master bedroom has an over-sized walking closet room with its own window. You will love the huge master bath with double vanity/sink, linen closet and glass door shower. On the other end of the hallway there are three bedrooms sharing another full bath with double vanity/sink. A laundry room conveniently sits next to the bedrooms with large capacity washer/dryer and plenty of room for racks and tables. This house has a two-car garage and two-zone irrigation system. The Windermere Trail club house is one block away from this home. A beautiful pool, two huge pavilions, and a playground are right next to the tranquil Lake Reams decorated with lush greenery and palm trees. A close-by Lakeside Village Park is little one's paradise with many slides, climbers and craw-through tubes. Located in Windermere, the upscale, finest and safest area of central Florida, zoned for top-rated schools, conveniently situated for quick access to supermarkets and additional shopping/dining, and with close proximity to great towns of Winter Garden, Horizon West and Dr Phillips, this gorgeous home won’t last long. Don’t wait, call today!

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Sherry Wang (484-744-4586)