Windermere Single Family Homes For Rent - 49 homes

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: Beautiful private studio apartment featuring an independent entrance and modern finishes. This unit includes a refrigerator, kitchen area, microwave, electric cooktop, washer and dryer. All appliances are practically brand new with less than 4 months of use. Enjoy the comfort of an independent central A/C and heating system. Perfect for 1–2 occupants looking for a clean, comfortable, and convenient place to call home.Monthly rent includes utilities. Located in the desirable Windermere area, close to shopping, dining, and major roads.

Listing is courtesy of: MELIN REALTY LLC (407-683-8713)

Listing Agent: Stefany De Faria (407-276-0318)

Remarks: This extraordinary Windermere lakefront estate offers refined living on the Butler Chain of Lakes. Located on one of the areas most desirable streets, the home features over $350K in recent upgrades, including a redesigned kitchen and fireplace, new windows and doors, fresh exterior paint, updated landscaping, and a new roof. A brand-new private dock provides direct access to Wauseon Bay. Spanning 5,639 sq ft, the home is designed to capture stunning water views throughout. A grand two-story foyer opens to elegant living spaces overlooking the resort-style pool and spa, highlighted by a striking 650-gallon saltwater aquarium. The gourmet kitchen blends style and function with Wolf and Sub-Zero appliances, quartz countertops, custom cabinetry, wine storage, and designer lighting. The main-level primary suite offers breathtaking lake views and a spa-like bath with soaking tub, dual vanities, and luxury finishes. Additional features include a wine cellar, private elevator, custom home theater, and an upstairs balcony with panoramic lake views. The second level offers three bedrooms, three baths, and a second laundry room. Outdoor living is built for entertaining with a summer kitchen, spacious patio, and private dock. A three-car air-conditioned garage completes the home. Owner-covered services provide a truly maintenance-free lifestyle, including weekly pool service, lawn care, professional aquarium maintenance, and high-speed internetall included in the rent. Experience luxury lakefront living at its finest. Resident Benefit Package: $49.00-month. Includes HVAC air filter delivery, Tenant Liability Insurance, Credit Reporting, Tenant Rewards Program, and much more! This property is eligible for deposit alternative coverage in lieu of a security deposit. For information and enrollment, please contact our leasing team and enjoy a deposit-free renting experience.

Listing is courtesy of: SPECIALIZED PROPERTY MANAGEMENT (407-682-3355)

Listing Agent: Jacob Rodriguez (407-745-8455)

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: This stunning and well-maintained single-family home is located in the gated Belmere of Windermere community, just steps from top-tier amenities including the pool, tennis courts, and fitness center, as well as nearby elementary, middle, and high schools, Zoned for A-rated schools. The spacious two-story layout features 5 bedrooms, 3 full bathrooms plus a half bath, a 2-car garage, high ceilings, and an abundance of natural light throughout. The primary suite located at the first floor offers a generous walk-in closet and a large, well-appointed bathroom and one suite upstairs. Conveniently situated near Publix, CVS, 7-Eleven, and a variety of other shops and services nearby, and just 5 minutes from Winter Garden Village. No smoking allowed.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Cristiane Carneiro Spindola Rocha Lima (407-766-9333)

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: Located in a highly desirable Windermere-area school district, this beautiful home features a conservation-view backyard and a playground directly in front of the property. The first floor features tile floor throughout for easy maintenance, while all bedrooms are on the second floor. A spacious loft upstairs provides the perfect space for relaxation, entertainment, or a home office. Conveniently located near Windermere High School, shopping, dining, and Walt Disney World, this home combines comfort with accessibility. Enjoy nightly Disney fireworks from the privacy of your backyard. Lawn service is included in the rent.

Listing is courtesy of: JOY ESTATE ENTERPRISE INC (321-754-9131)

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

Remarks: Sited in the Preserve at Lakes of Windermere, a gated community, this three-bedroom, two-bathroom home sits in a highly desirable location. This single-story home offers a bright, open-concept floor plan with a formal living room, dinning room, family room, kitchen and breakfast nook. The private master bathroom offers a garden tub, separate glassed shower, dual sinks and large walk-in closet. Great backyard area with covered lanai facing conservation. You will not need a car to get to the community's amenities from this home. Enjoy nightly fireworks from your front porch. Lakes of Windermere is conveniently located in the heart of Windermere and offers great amenities, including swimming pool, picnic area, playgrounds and a beautiful lake gazebo. It is just minutes away from Disney attractions, I-4, Winter Garden Grove Shopping and Restaurant Center, SR 408, Florida Turnpike and much more.

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

Listing Agent: Maria Quintero (407-509-0849)

Remarks: Welcome to this beautiful 3 bedroom, 2.5 bathroom home for rent in the highly desirable Windermere Trails community! This spacious two-story home features all bedrooms conveniently located upstairs along with a loft area, perfect for a second living space, office, or playroom. The upstairs laundry room includes a washer and dryer for added convenience. Enjoy a functional layout, a 2-car garage, and a prime location close to shopping, dining, and everyday conveniences. Located in a top-rated school district, this home offers access to amazing community amenities including a resort-style pool, playground, and park areas. Nature lovers will appreciate being just a short 5-minute drive from Tibet-Butler Preserve, offering scenic trails, wildlife, and outdoor activities. Don’t miss the opportunity to live in one of Windermere’s most sought-after communities—schedule your showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Anastasiia Zbihla (813-992-3395)

Remarks: Welcome to your new home!! Conveniently situated within the charming Windermere area, you'll find this gem House, fully furnished, 1-Master Suite, 2-bedrooms, 2 and 1/2 bathrooms, nestled within the Windermere Sound community. Opening the entry door (with a digital code locker), you will find a beautiful spacious living room, well decorated and plenty of natural light coming trough the double windows, furnished with a big couch, accent chairs and leather benches, where you can gather your family and friends. Still on the first floor, an open floor view with kitchen, dining room and TV room all together. By the kitchen there is a big storage room. The laundry is equipped with washer, dryer and cabinets. On the second floor, a spacious Master Suite, walking closet with custom cabinets, master bathroom with granite counter, double sink, bathtub and shower. Two more gorgeous bedrooms (jack&Jill), beautiful furniture, wallpaper, TV’s, walking closet, so many things that will make your home wonderful. The location is also great, with great schools, few minutes away from Publix, Walgreens, Gym and from restaurants and stores.

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

Listing Agent: Sergio Figueiredo (321-512-1726)

Remarks: Welcome home to this charming 3-bedroom, 2-bath home located in the desirable Silver Woods area of Windermere! Available for immediate move-in, this property offers a comfortable and functional layout with spacious bedrooms and bathrooms, a bright kitchen with ample counter and cabinet space, and a large lot perfect for enjoying outdoor living. Lawn care is included with rent! Conveniently located near shopping, dining, major roadways, and top-rated schools, this home combines comfort and convenience in one of Central Florida’s most sought-after areas. 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 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: GOLF FRONT!! Beautiful 4-Bed, 3-Bath Home for Rent in the Exclusive Keene’s Pointe Golf Community Nestled in the sought-after and secure gated community of Keene’s Pointe, this stunning single-story home offers a rare opportunity to live in a neighborhood renowned for its strong sense of community and premium amenities. Community Features: • Gated with 24/7 Manned Security: Peace of mind and privacy. • Convenient Amenities: Enjoy access to an on-site restaurant, fitness center, tennis courts, and more—all just a short distance from your doorstep. Property Highlights: • Prime Location: Backing onto the driving range, enjoy serene views of practicing golfers without worrying about stray golf balls. Evenings are quiet and peaceful. • Backyard Oasis: The screened-in pool and spa, complete with heating, create a perfect space for relaxation. A fully equipped summer kitchen adds to the charm for outdoor entertaining. • Spacious Layout: Inside, the home features 4 generously sized bedrooms and a well-designed kitchen with top-of-the-line GE appliances. • Freshly Painted: The interior was recently refreshed in December, offering a clean and inviting atmosphere. • All solid f looring throughout. IAmple Garage Space: A 3-car garage includes a dedicated space for your golf cart. Added Value: • Yard maintenance, pool service, and pest control are included in the rental, providing a relaxed lifestyle. Don’t miss this incredible opportunity to call Keene’s Pointe your home.

Listing is courtesy of: WINDERMERE INTERNATIONAL REALTY (407-421-6241)

Listing Agent: Hans Welbergen (407-701-6814)

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: Available starting on AUGUST 1, 2026. LAWN CARE & POOL MAINTENANCE INCLUDED — Move in and enjoy from day one. Live the Florida luxury lifestyle without the hassle. Nestled behind the exclusive 24-hour guard-gated gates of The Reserve at Belmere — one of Windermere's most prestigious communities — this stunning Mediterranean-style estate offers over 4,000 square feet of refined living with every detail thoughtfully designed for comfort and elegance. Space for Every Chapter of Life with 6 bedrooms, 4.5 bathrooms, a dedicated home office with French doors, and a generous bonus room that's perfect as a playroom, home theater, or game room, there's space here for everyone — whether you're working from home, raising a family, or hosting guests in style. The gourmet kitchen is the true heart of this home, featuring a gas cooktop, double ovens, granite countertops, a breakfast bar, and a sunny breakfast nook. It flows seamlessly into a warm, inviting family room with a fireplace — the kind of space where everyday moments feel special. Luxurious Touches Throughout with Crown molding, coffered ceilings, and a grand foyer set the tone from the moment you walk in. The downstairs primary suite is your personal retreat, complete with serene pool views and a spa-inspired bath featuring a jacuzzi tub, walk-in shower, and dual vanities. Upstairs, four additional bedrooms — including a convenient Jack-and-Jill configuration — offer flexibility and privacy for family and guests alike. Your Own Backyard Oasis — Maintained for You. Step outside to a beautifully appointed outdoor living space with a large paved patio, summer kitchen, heated pool, and spa. Because lawn and pool care are included in your lease, you can focus on enjoying it all rather than maintaining it. Residents enjoy exclusive access to: Fully equipped fitness center, two tennis courts & basketball court Sand volleyball court, Fishing pier, Beautifully maintained playground, Stunning waterfront setting throughout the community. Location That Checks Every Box: The Reserve at Belmere delivers peace of mind alongside unmatched prestige. Homes of this caliber rarely come available for lease — schedule your private tour today and make this exceptional property your next home.

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

Listing Agent: Yana Ogor (904-400-4192)

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)