Windermere Single Family Homes For Rent - 52 homes

Remarks: This beautiful move-in ready home offers 4 bedrooms, 4 bathrooms, plus a dedicated office/flex room, providing the perfect blend of comfort, space, and functionality. The first floor features elegant tile flooring throughout and a spacious primary suite conveniently located on the main level for added privacy. Upstairs, you'll find a junior master suite along with a versatile loft/bonus area ideal for a media room, playroom, or home office. Designed for both everyday living and entertaining, the home includes formal living and dining areas, a separate family room, and an impressive kitchen featuring stainless steel appliances, a breakfast nook, high ceilings, and elegant 8-foot interior doors that create an open and airy feel throughout. Recent updates include newly completed exterior painting and newer interior paint. Located in a highly desirable family-friendly community with excellent schools, future clubhouse amenities, a community swimming pool, and a large scenic lake offering beautiful water views and relaxing surroundings. Tenant occupied. 24-hour appointment required for all showings. Tenant Responsibilities: Power, water, cable, internet, phone, lawn maintenance, and irrigation head replacements.

Listing is courtesy of: AAA GLOBAL VENTURES PA (407-717-5232)

Listing Agent: Asher Chen (407-717-5232)

Remarks: This single story property in the popular community of Summerport is ready for new tenants, the tiles have just been professionally steam cleaned throughout and there is no carpet in the property, house was painted recently and new laminate flooring added to the bedrooms. The property benefits from a screened porch on the rear with an extended driveway that has recently been pressure washed. Easy access to the new town of Hamlin, great schools and shopping

Listing is courtesy of: WENDY MORRIS REALTY (407-575-5392)

Listing Agent: Wendy Morris (407-575-5392)

Remarks: Experience Lakefront Luxury Living - where every day feels like a vacation. Prepare to be captivated by this fully renovated three-bedroom, three-bath lakefront home on the highly sought-after Lake Butler. Part of the Butler Chain of Lakes, featuring 13 connected lakes. A true retreat that blends resort-style amenities with refined design. Nestled on pristine waterfront, this property offers breathtaking views from virtually every room, creating the ultimate backdrop for serene living and effortless entertaining. At the water's edge, enjoy a two-story dock complete with a hydraulic boat slip and jet ski lift, plus your own private boat ramp, a rare and coveted feature for lake enthusiasts. After a day on the water, unwind in the solar-heated swimming pool, framed by panoramic lake vistas. Inside, the heart of the home is the expansive luxury kitchen, thoughtfully designed with high-end finishes and an abundance of upgrades, including spice organizers, pull-outs, and generous storage solutions. Multiple flex spaces offer endless possibilities for a home gym, office, or den. The main level master suite is a peaceful sanctuary with sweeping lake and pool views. It connects to a conditioned Florida room, perfect for morning coffee or for unwinding at sunset. Upstairs, a bright loft area leads to two spacious bedrooms, connected by a stylish Jack-and-Jill bathroom. One of the bedrooms opens to a private lakeview deck, offering a stunning vantage point over the water. Additional features elevate this home even further! A well-equipped greenhouse, an air-conditioned shed with a garage door, perfect for storing jet skis, and multiple beautifully finished indoor and outdoor living spaces designed for comfort, elegance, and entertaining. Whether you're boating, lounging by the pool, tending your greenhouse, or simply enjoying the peaceful waterfront scenery, this home offers an unparalleled lifestyle. Must meet resident selection criteria. 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: 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: A rare opportunity to lease a furnished executive estate in the prestigious guard-gated community of Lake Butler Sound. Perfect for corporate relocations, executive families, or those building, renovating, or transitioning between homes, this turnkey residence offers flexible lease terms in one of Windermere's most sought-after communities. Thoughtfully designed for comfortable everyday living and entertaining, the home features a gourmet chef's kitchen with premium appliances, a spacious first-floor primary suite, executive office, game room with full bar, private theater, and an expansive outdoor living area complete with a resort-style pool, spa, fireplace, and summer kitchen. Conveniently located within an exceptional school district and less than 10 minutes from Windermere Preparatory School, the home provides unmatched convenience with proximity to major business centers, leading hospitals, world-renowned golf, upscale dining, shopping, major expressways, and Orlando's premier attractions. This exceptional move-in ready residence offers the privacy, security, and resort-style lifestyle discerning tenants expect. Private tours available by appointment.

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

Listing Agent: Julian Correa (407-990-2360)

Remarks: Beautiful 4-bedroom home in the desirable Windermere area. Featuring an open floor plan, spacious living areas, a modern kitchen, and a private backyard perfect for entertaining. Conveniently located near top-rated schools, shopping, dining, and major attractions. Move-in ready and a must-see!

Listing is courtesy of: MD3 HOMES LLC (407-557-8810)

Listing Agent: Monica Duran (407-702-5796)

Remarks: Available on AUGUST 1, 2026. Move in and enjoy from day one. Inside exclusive 24-hour guard-gated Reserve at Belmere — one of Windermere's most desirable communities. Thr Estate offers over 4,000 square feet of living space. 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 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. Step outside to a beautifully appointed outdoor living space with a large paved patio, outside full bathroom, summer kitchen. Take advantage of community amenities: fitness center with water views, two tennis courts & basketball courts, volleyball court, and fishing pier. The Reserve at Belmere delivers peace of mind alongside unmatched prestige. Call leasing agent to schedule private tour. Additional fee : $150 monthly pool care

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

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

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 your dream home in a beautiful cul-de-sac, nestled in a secure, gated community and zoned for top-rated Windermere schools. This fully remodeled, move-in-ready home offers 5 spacious bedrooms plus a large bonus area on the second floor, complete with a half bath. The upgraded chef’s kitchen boasts all new appliances, perfect for entertaining. Relax in your private resort-style pool, or enjoy the convenience of lawn maintenance, pool service, and pest control—all included in the rent. Plus, you’re just minutes from Disney, major highways, and a variety of shops and restaurants. This is the perfect place to call home!

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

Listing Agent: Sevara Botirova Patel (407-242-9546)

Remarks: FOR RENT | Luxury 5-Bedroom Home with Private In-Law Suite in Windermere Welcome to this beautifully updated 5-bedroom, 4-bathroom residence offering 3,365 square feet of elegant living space in one of Windermere’s most desirable communities. This exceptional two-story home has been thoughtfully upgraded with a brand-new roof, two new HVAC systems, updated flooring, fresh paint, and a renovated chef’s kitchen, creating the perfect blend of luxury, comfort, and functionality. Step through the impressive leaded-glass entry doors into a grand foyer with soaring cathedral ceilings and an inviting open layout. The thoughtfully designed three-way split floor plan features hardwood floors, tray ceilings, crown molding, formal living and dining areas, and abundant natural light throughout. The gourmet kitchen is the heart of the home, showcasing granite countertops and backsplash, stainless steel appliances, a large center island with storage, breakfast bar seating, and ample space for entertaining. The spacious primary suite offers private access to the screened lanai and features a luxurious bathroom with dual vanities, a garden tub, walk-in shower, and oversized walk-in closet. One of the home's most desirable features is the private upstairs In-Law Suite, complete with its own bedroom, full bathroom, living area, and dedicated HVAC system—perfect for guests, multigenerational living, a home office, or private retreat. Additional features include: ? 3-Car Garage ? Indoor Laundry Room with Utility Sink ? Screened Covered Patio ? View Disney Fireworks from Home ? Community Pool, Playground & Dog Park ? Top-Rated Schools Including Windermere Prep Nearby ? Minutes to Winter Garden Village, Disney, 429 Expressway, Butler Chain of Lakes, Shopping, Dining & Entertainment This home offers the ultimate Florida lifestyle with space, privacy, and an unbeatable location. Available for immediate occupancy. Schedule your private showing today and discover why this Windermere home is truly one of a kind.

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

Listing Agent: Patricia Zimath, Llc (321-318-1050)

Remarks: Looking for seclusion? One plus acre waterfront. No HOA. Adorable, clean available June 1st. Bring your boat, RV, pets. Quiet treed drive located near the Town of Windermere. Complete with stainless appliances, washer, dryer. Large screened porch. Tile floors throughout. Decorative fireplace in family room. Room to Breathe!! Check it out today. For Application: https://apply.link/rhwVwSc

Listing is courtesy of: UPSIDE REAL ESTATE INC (407-308-5750)

Listing Agent: Judy Black (407-810-1803)

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: 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: 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: 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)