Windermere Single Family Homes For Rent - 54 homes

Remarks: RECENTLY RENOVATED within the gates of Isleworth Golf and Country Club on a lovely cul-de-sac, you will discover this Golf Villa, boasting over 3,500 square feet of space. With 3 bedrooms plus an office, which could easily be used as a 4th bedroom, this charming villa has a spacious master suite with a garden view step-down shower, a notable kitchen with breakfast nook, formal dining room, and living room with a gas fireplace. Enjoy the outside grill area and large fenced-in yard. The home has an oversize 2 car garage with a golf cart entrance for those golf enthusiasts.

Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)

Listing Agent: Michelle Corbin (407-491-2690)

Remarks: WATER & ELECTRIC INCLUDED!! MOVE IN JUNE!! Welcome home! 3X2.5 bath 2 story main house 2000 sq ft!! Spacious living area! Perfect for entertaining as it opens to the amazing kitchen that featuring elegant 42" cabinets with beautiful Corian countertops. Elegant French doors in the living room lead to the beautiful view of the courtyard in back. All bedrooms are on the 2nd floor! Primary suite has inviting garden tub, walk-in shower, and an enormous walk-in closet as well as separate vanities!! washer/dryer hookups in utility room as well. A/C, water heater and washer & dryer are new. Resort-style amenities such as exercise room, clubhouse, pool, tennis courts, basketball courts, volleyball/beach area, and a tranquil dock area with amazing views. Easy access to shopping, dinning, and major highways!! Within an approximate 15 min drive to Disney parks! Water and electricity included! Lawn care HOA responsibility. -Garage apartment is rented separately and not included as part of the rental of main house.- -Water & electricity shared by main house and garage apartment. In the event total power & water exceeds $500.00 on any particular month, each tenant/unit will pay overage proportionally based on the average of # of occupants & square footage under AC.- (1x1 garage apartment rented separately but owner will consider renting all on one lease with main house if you are interested (rental price to include main house and 1x1 garage apartment would be negotiated) - 1x1 apartment above garage offers - 380 sq ft of living space under AC with private entrance. Wonderful full kitchen, full bath, spacious living area, and 1 private bedroom- ideal for guests, extended family, office space etc. )

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Joanne Bracero (407-399-8469)

Remarks: Beautiful 3 bedroom, 2 bathroom single family home located in Windermere. Great kitchen with stainless steal appliances, Master bedroom has large walk in closet. Master bathroom offers dual vanities, soak tub, and separate walk in shower. All rooms are spacious and have laminate floor. A+ rated schools located just minutes from shopping, dining, golfing, and much more. MUST SEE!!

Listing is courtesy of: SUNNY 365 REALTY GROUP (407-574-7048)

Listing Agent: Isabel Sirizzotti (407-361-8236)

Remarks: Welcome to Waterstone Windermere, with tranquil living and charm, this area boasts connecting lakes, ideal for boating and walking. this property consist of 5 bedrooms, 5 full bathrooms and 2 half baths. it’s 10-15 mins drive from Disney many restaurants and bars, Reputable schools and many other features.

Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-299-3000)

Listing Agent: Kimroy Mussington (407-299-3000)

Remarks: Windermere Home, Backs Up To Wooded Area! This spacious and beautifully maintained 4-bedroom, 3.5-bathroom home offers 2,632 square feet of living space and backs up to a serene, wooded area, providing privacy and scenic views. Freshly painted throughout, the home features a modern kitchen with granite countertops, stainless steel appliances, and ample cabinet space. Enjoy a formal dining room, generously sized bedrooms, and a convenient second-floor laundry room equipped with a front-load washer and dryer. Additional features include a three-car garage, community pool, and playground. Lawncare Included! Sorry, No Roommates & No Pets Allowed!! Application Fee: $50/adult (18+) Full Credit/Skip/Eviction/Background check is done on all applicants. **Please have the following documents ready to attach as JPEG or PDF: Drivers License & Pay Stubs (3)**

Listing is courtesy of: PREMIER MANAGEMENT GROUP INC (407-370-4400)

Listing Agent: Ken Warren (407-370-4400)

Remarks: 3-bedroom, 2.5-bath single family pool home in Lakes of Windermere community. Spacious layout with separate living, dining, and bonus room. The kitchen features a breakfast bar, which is open to the formal dining and dinette areas that overlook the pool/patio. Pool deck/patio is fully screened, and pool service is included. Washer/Dryer are located in the interior laundry room, leading to a two-car garage. There is a total of 2,790 square feet, and 2,229 square feet under air. Community amenities include a pool, picnic area, tennis court, and playground. All information is deemed reliable, but not guaranteed. Listing Brokerage does not discriminate on the basis of race, color, religion, national origin, sex, disability or familial status. All residents are enrolled in the Resident Benefits Package (RBP) for $50.00/month as additional rent, which includes renters insurance, credit building to help boost your credit score with timely rent payments, our best-in-class resident rewards program, $1M Identity Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, online resident portal for easy online rent payments & maintenance reporting, HVAC air filter delivery (for applicable properties), and much more! More details available upon application.

Listing is courtesy of: WILSON MANAGEMENT GROUP (407-896-1200)

Listing Agent: Lionel Hebert (407-641-0975)

Remarks: Located in the gated community of Casa Del Lago in Windermere, featuring just 88 luxury homes surrounding Lake Burden, this neighborhood offers an exceptional setting near top-rated schools and only minutes from Orlando’s most popular destinations, including major highways, airports, shopping, dining, and world-renowned attractions. Built by one of the nation’s top private homebuilders, David Weekley Homes, this nearly 4,000-square-foot residence is thoughtfully designed for both everyday living and entertaining. The home features four bedrooms on the first floor, including two bedrooms positioned on the same side of the home that are connected by a shared playroom or bonus space, while each bedroom maintains its own private en suite bathroom. A formal dining room, dedicated private office, and spacious family room provide multiple areas for gathering and daily living. A convenient pool bath is located just off the main living area with direct access to the pool patio. Upstairs, a large loft-style game room offers flexible living space along with a private fifth bedroom featuring its own full bathroom, making it ideal for guests or multigenerational living. Outdoor living is equally impressive with a luxurious paver patio, screened-in pool, and low-maintenance turf backyard, creating a private retreat perfect for year-round Florida living. The home is also fully wired with a comprehensive CCTV security system featuring 21 cameras for added security and peace of mind. Residents also enjoy the prestigious opportunity to become members of the Golden Bear Club, featuring a full-service golf course and clubhouse located in the neighboring community of Keene’s Pointe. Homes in Casa Del Lago rarely come to market, making this a unique opportunity to live in one of Windermere’s most exclusive gated communities.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Matt Kester (772-494-8550)

Remarks: Welcome home! This 4-bedroom, 3.5-bath home is available for immediate move-in! 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. Enjoy the large back yard and a screened-in patio!! Upstairs features a large loft area and a lovely porch to relax! You will also have access to the gorgeous community swimming pool, playground, and basketball court which are all located just steps from the house. 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. Lawn care is included with rent!

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

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

Remarks: Fully Furnished Executive Rental in downtown Windermere! Welcome to Sunrise on the Lake, a beautifully renovated, fully furnished executive home on Lake Bessie in Windermere. Tucked along winding lakeside roads, this peaceful retreat is perfectly positioned for stunning sunrises, refreshing lake breezes, and panoramic water views. From the moment you arrive, you will appreciate the exceptional curb appeal and expansive front deck overlooking the lake. Chicago brick pavers lead to a mostly single-level, open-concept layout designed for comfort and entertaining. The European inspired living space features a bright dining area with large picture windows and a welcoming family room with premium amenities, including a Sony flat-screen TV, Bose soundbar, electric fireplace, stand-up arcade with 100+ games, foosball table, plus board games and books. The fully equipped kitchen offers stainless steel appliances, remarkable lake views, and opens to the dining area with comfortable seating for eight. Bedrooms provide relaxing, private spaces with views of the home’s half-acre setting. Outside, enjoy a private moon garden with orchids, a shaded dining area beneath a grand oak tree, and a spacious deck perfect for soaking up the Florida sun and enjoying the calm water. The home has recently undergone a complete remodel, with new or newer furnishings throughout, including updated appliances.

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

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

Remarks: PLENTY OF SPACE in this beautiful 5-bedroom/4-bath with fully fenced backyard located in desirable Windermere Trails. The home has tile and luxury vinyl throughout (NO CARPET) with plenty of room for families or individuals. Large open floor plan; kitchen with granite countertops, stainless appliances and walk-in pantry; as well as downstairs guest bedroom with ensuite/Jack & Jill bathroom. The master bedroom with large ensuite is on the second floor along with 3 other bedrooms, 2 full bathrooms, laundry room and spacious bonus room. Community includes large pool, playground, cabanas, greenspace and fitness parks, walking trails and dock access. Conveniently located close to highly-rated schools, shopping and restaurants including Lakeside Village Center, Westside Shoppes and Winter Garden Village, as well as Disney, FL-429, FL-408, and I-4. -- No short-term, AirBnB or roommates. Renter’s insurance required.

Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)

Listing Agent: Carolyn Hunt (407-257-0937)

Remarks: Keene's Pointe gated/24-hour attended home featuring 4 bedrooms, 4 full/2 half baths, formal living and dining rooms, loft, and bonus/game room. This spacious home has low maintenance laminate flooring throughout. The master suite is on the first floor with access to the lanai, walk-in closet with customized shelving and bath with tub, shower and two vanities. The kitchen and family room are centered in the home with multiple doors to the lanai. The family room has a two-story ceiling with gas fireplace and built-ins. Upstairs you will find a loft with built-in cabinetry that can also be a study, bonus/game room over the garage with full bath and three additional bedrooms (one is an en-suite and the other two share a hall bath). The back yard is spacious and has a large pool/spa with fencing and covered lanai. There is also a three car garage large enough to house a golf cart. Shallow well for irrigation, newer roof and gutters are just some of the great features of this home.

Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)

Listing Agent: Teresa Stewart (407-493-3057)

Remarks: Stunning Beautiful Upgraded home in the desirable Wickham Park community in heart of Windermere. NO carpet. Perfect location. Top rated schools. Rent includes hoa fee and lawncare. Well-maintained 4 bedroom & 2.5 bath & 1 loft/retreat upstairs & 2 car garage on front. Sizable back yard with extended pave. Open floor plan with lots of upgrades. Great natural light in the whole house. Master bedroom downstairs with upgraded bath tub, shower, vanity, lighting fixtures and walk-in closet. Upstairs there are 3 bedrooms and 1 loft area for multiple game/retreat/study/open office. Community amenities includess clubhouse pool, walking/biking trails, dog park, playground. Perfectly convenient for the grocery shoppings, restaurants, schools, entertainment, daily living essentials. Closed to Disney World. Short drive to downtown of Orlando, Winter Garden. Schedule a showing today!

Listing is courtesy of: YORK MILLS REALTY LLC (626-328-8535)

Listing Agent: Jacky Liu (407-921-5670)

Remarks: Located in the highly sought-after Summerport community in Windermere, this move-in ready home offers the perfect combination of location, comfort, and everyday convenience. Zoned for highly rated schools and just minutes from Horizon West, Disney, downtown Winter Garden, shopping, dining, and major roadways including SR-429 and the Florida Turnpike, the location is hard to beat. Inside, you’ll find a spacious and functional floor plan featuring brand-new carpet, fresh interior and exterior paint, granite countertops, wood cabinetry, a gas range, gas water heater, and abundant natural light throughout. The flexible bonus room is ideal for a home office, playroom, gym, or additional living space. The primary suite features a walk-in closet and private en-suite bathroom designed for comfort and privacy. A new washer and dryer are also included, making this home truly move-in ready. Step outside to a screened-in patio overlooking a peaceful pond view, creating the perfect setting for morning coffee or relaxing evenings with no rear neighbors directly behind you. The front yard landscaping and charming curb appeal further enhance the home’s welcoming feel. Residents of Summerport enjoy access to resort-style amenities including a community pool, fitness center, tennis courts, parks, playgrounds, sidewalks, walking trails, and scenic lakes throughout the neighborhood. With its ideal location, recent updates, and desirable community amenities, this home is an excellent opportunity in one of Windermere’s most popular communities.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Evan Caulfield (407-432-9767)

Remarks: Luxury one-level Mediterranean Style home located in the highly desirable Enclave community at WINDERMERE. This elegant home is Energy Star Certified and also come with Solar Panels, monthly electric bill is only around $33! Step into the grand entryway with extensive natural light throughout, this 4 bedrooms, 2 baths with an office home deliver a bright open atmosphere. Open floor open, well maintained with ceramic tile on living area and laminate floor on all bedrooms. The master bedroom, the living room and the eating area overlook the tranquil pond at the back, not only creating a beautiful water view, but also providing a peaceful backdrop and exceptional Privacy. Relax in the screened patio or the back yard to enjoy the peaceful water scenery. The chef inspired gourmet kitchen features granite countertops, 42" cabinetry and SS Appliances. The Master Bedroom features elegant tray ceiling. Master bathroom has a garden tub, spacious shower, dual vanities and a large walk-in Closet. All bedrooms have walk-in closets with custom built-in shelving. Great school district! Just a few minutes to Windermere High School and Windermere Preparatory School. Walking distance to Sunset Park Elementary. Enclave is a beautiful community features all roof tile luxury houses. It is located on Chase Road next to Keene’s Point and Gold Bear Golf and Country Club. Easy access to SR 429, Turnpike and 408. Close to Disney Theme Parks. Shopping, dining and attractions are all within a vibrant area. Windermere ranked number one as the best place to live for suburbanites in Florida. Must see! Call now to schedule a showing!

Listing is courtesy of: SUNSHINE REALTY & PROP. MGNT (407-341-8754)

Listing Agent: Man Ching Wong (407-341-8754)

Remarks: Discover refined Florida living in this stunning 5-bedroom, 3.5-bathroom home located in the sought-after Ashlei Park community in Windermere. Designed with both elegance and functionality in mind, this spacious residence offers an exceptional layout ideal for comfortable family living and entertaining. Step inside to find bright, open living spaces filled with natural light, complemented by stylish finishes and generous room sizes throughout. The gourmet kitchen seamlessly connects to the main living areas, creating the perfect setting for everyday living and hosting guests. The beautifully landscaped backyard provides a private retreat where you can relax and enjoy the Florida lifestyle year-round. The outdoor patio is ideal for barbecues, gatherings, and peaceful evenings outdoors. Additional features include a two-car garage and abundant storage space throughout the home. Conveniently located in the highly desirable Windermere area, residents enjoy easy access to top-rated schools, premier shopping, dining, entertainment, and major attractions throughout Central Florida. This exceptional Ashlei Park home offers the perfect combination of luxury, comfort, and convenience. Schedule your private showing today and experience everything this beautiful rental property has to offer!

Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)

Listing Agent: Simone Pinto De Almeida Santos (407-371-2893)

Remarks: Lease or Lease Purchase available! Experience true lakefront living on the famed Butler Chain of Lakes in this exceptional custom home offering 137 feet of pristine shoreline on nearly one acre of high, dry land. Enjoy sweeping panoramic water views, refreshing lake breezes, and even nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and enter through an impressive solid cedar door with artisan leaded glass. Inside, the great room features soaring 23’ cathedral ceilings and a dramatic Tennessee river rock fireplace. The showstopping formal dining room is wrapped in oversized picture windows that perfectly frame the lake. Designed for comfort and convenience, the majority of the living space including all bedrooms is on the main level. The chef’s kitchen is fully equipped with solid wood cabinetry, granite countertops, Sub-Zero refrigerator, Thermador gas cooktop with exhaust, Bosch double ovens, wet bar, walk-in pantry, and a bright breakfast area with incredible water views. The spacious primary suite is a private retreat with its own screened lanai and a spa-style bath featuring a shower, jetted tub, dual vanities, and three walk-in closets. Secondary bedrooms are generously sized with ample closet space and well-appointed baths, including a steam shower. Outdoor living is unmatched with mature landscaping and colorful gardens, plus a motorized screened lanai with a summer kitchen featuring a pizza oven, prep area, grill, refrigerator, and TV. Relax by the pool, heated spa, and gas firepit, all positioned to take advantage of the desirable southern exposure for comfortable outdoor enjoyment. Boaters will love the rare, partially enclosed grandfathered-in dock with boat lift and side jet-ski lift. Additional features include newer doors and windows, a tile roof, and a custom floor plan maximizing lake views throughout. The Lakes community also offers a boat ramp and tennis courts. Enjoy Windermere living on the Butler Chain without the traffic, just minutes to major roads, top schools, shopping, and dining. This rare, well-built lakefront home is ready to welcome you.

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

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

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: 5 bedroom, 3 bath home nestled in the community of Windermere Sound. Located near schools, parks, shopping and more, this home is waiting for you! A Large house like this, is sure not to last long.

Listing is courtesy of: BLUEHOUSE REALTY GROUP LLC (929-391-3985)

Listing Agent: Donny Hang Fung (929-391-3985)

Remarks: Stunning upgraded house in Windermere Isle in Gas community, Fully Fenced, NO Carpet in the house. Rent includes full lawn services and spectrum cable and internet service, save a lot bill. Two downstairs bedrooms are perfect for a guest bedroom and a home office. Tankless water heater. Beautiful engineer wood flooring and Ceiling fan with remote control in all rooms. Popular Designer paint, crown molding, Chef kitchen, backsplash, stainless steel appliances with gas stove, walk-in pantry and Office Nook area. The huge Loft gives you an extra space for a secondary living area. The MASTER SUITE has a large double walk-in closet. Unwind from the day in your GARDEN BATH with soaking tub and semi-frameless glass shower with double shower head with rain showerhead. Another 2 bedrooms have jack and jill bathroom to share, Second floor laundry room with sink. Screen lanai with ceiling fan for enjoying outdoor living. Epoxy garage floor paint. Windermere Isle offers residents a Community Pool, Cabana and Playground. Top rated school, Located close to 429, Disney and Hamlin Shops.

Listing is courtesy of: AGENT GROUP REALTY (843-656-0550)

Listing Agent: Li Xue (407-919-3796)

Remarks: Vacant! Great Location! Great House!! Must See!!! Move into this home inside the lovely Berkshire Park community in the very desirable town of Windermere. This house is full of upgrades and is an Energy Star certified home. Downstairs has tiled floors, and a private study room. It oversees the front porch. Kitchen has all appliances and granite countertop. It opens to the Great Room and provides the best place for family and friends' gatherings. You can also enjoy Disney fireworks every night. Downstairs there is a large master bedroom, upstairs has two bedrooms and large play space. Master bathroom has double sink, granite countertop, and a large shower room. Laundry room with a large space for storage. This highly sought-after community features quality built and well-maintained homes. Amenities include walking trails, playgrounds, and a huge community pool. 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 history, no BAD RENTAL 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)