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Windermere, FL Homes for Rent

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  • /45

    $4,980 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,136 Sq Ft
    • House for Rent

    7023 Kiwano Way, Windermere, FL 34786

    Welcome to this beautiful, spacious two-story home located in the highly sought-after Sanctuary at Lakes of Windermere. This nearly new residence offers 5 bedrooms, 4.5 bathrooms, a private home office, an upstairs bonus room, and a thoughtfully designed floor plan that perfectly blends luxury, comfort, and functionality. Elegant French doors open to a dedicated home office, providing the ideal

    Agent Photo

    Wendy Fischer

    PREMIER SOTHEBYS INT'L REALTY

    7023 Kiwano Way, Windermere, FL 34786
  • /117

    Starting at $1,927

    Total Monthly Price

    • 1 - 3 Beds

    6506 San Francesco Way, Windermere, FL 34786

    A beautiful community with luxury one, two and three-bedroom apartment homes with a Mediterranean flair.We invite you to transport yourself to an upgraded level of luxury right at your front door. Every finish is hand-selected with the finest touch to make every day surpass the next. Our elegant, resort-inspired amenities have a level of sophistication you'll find awe-inspiring day and night.

    Venetian Isle

    6506 San Francesco Way, Windermere, FL 34786
  • /91

    Starting at $1,659 Per Month

    • 1 - 3 Beds

    13644 Tortona Ln, Windermere, FL 34786

    Addison At Windermere is located at 13644 Tortona Lane Windermere, FL and is managed by GrayCo Properties, LLC, a reputable property management company. Addison At Windermere offers 1 to 3 bedroom apartments ranging in size from 592 to 1508 sq.ft. Amenities include Microwave and more. This rental community is pet friendly, welcoming both cats and dogs. Property is located in the 34786 ZIP code.

    Addison At Windermere

    13644 Tortona Ln, Windermere, FL 34786
  • /87

    Starting at $1,945 Per Month

    • 1 - 2 Beds

    1231 Arya Way, Ocoee, FL 34761

    Discover refined active adult living at Arya at Windermere, a premier 55+ community offering luxury and vibrancy of Windermere. Our spacious one- and two-bedroom residences feature impressive finishes and thoughtful designs that elevate everyday living. Residents enjoy resort-style amenities including a massage room, steam room, and a host of social and wellness opportunities in a pet-friendly

    Arya at Windermere

    1231 Arya Way, Ocoee, FL 34761
  • /51

    Starting at $1,479 Per Month

    • 1 - 3 Beds

    11353 Citra Cir, Windermere, FL 34786

    Experience the finest apartments in Windermere, Florida at The Citra at Windermere. Our apartment community offers a variety of distinctive one, two, and three bedroom apartment homes. Conveniently located, Citra at Windermere is walking distance to shopping, restaurants and entertainment. In addition, we are located within some of the top rated schools in Orange county, including Bay

    Citra at Windermere

    11353 Citra Cir, Windermere, FL 34786
  • /43

    Starting at $1,745 Per Month

    • 1 - 3 Beds

    7826 Crosswater Trail, Windermere, FL 34786

    TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Discover resort-style living at MAA Crosswater in Windermere, FL. Garden tubs, double vanity sinks, and washer/dryer units are featured in these one-, two-, and three-bedroom apartment homes. Admire the lake view from our sparkling swimming pool and cabana, or dig your toes in the sand \"beach\" lounging area.

    MAA Crosswater

    7826 Crosswater Trail, Windermere, FL 34786
  • /25

    Starting at $1,810

    Total Monthly Price

    • 1 - 3 Beds

    101 Casa Mirella Way, Windermere, FL 34786

    Welcome to Casa Mirella Apartments, where lakeside living meets luxury in the heart of Windermere, FL. Enjoy sunny Florida days by the resort-style swimming pool, stay active in the fully equipped fitness center, or relax with friends at the picnic area with outdoor grills. Your furry friend will love the dog park at our luxury apartments in Windermere, FL, and you’ll appreciate the peace of mind

    Casa Mirella

    101 Casa Mirella Way, Windermere, FL 34786
  • /35

    Starting at $1,723 Per Month

    • 1 - 3 Beds

    11598 Lachlan Ln, Windermere, FL 34786

    TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Call MAA Windermere home in Windermere, FL. Our one-, two-, and three-bedroom apartment homes have all of the modern conveniences you're looking for. Select apartments feature spacious showers, double vanities, and soaking tubs. All units come with a washer/dryer and lots of natural light. Enjoy an expansive

    MAA Windermere

    11598 Lachlan Ln, Windermere, FL 34786
  • /16

    $3,150 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,476 Sq Ft
    • House for Rent

    5457 Gemgold Ct, Windermere, FL 34786

    EXCITING NEWS: WE ARE CURRENTLY RENOVATING THIS HOME! NOTE THAT THE PHOTOS SHOWN REPRESENT THE HOME BEFORE RENOVATION AND DO NOT REFLECT ANY UPDATES. PLANNED IMPROVEMENTS INCLUDE: NEW LVP FLOORING AND NEW HARD SURFACE COUNTERTOPS. APPLY TODAY OR ASK YOUR LEASING SPECIALIST FOR MORE DETAILS! Apply now or schedule your self-tour today and take the first step toward getting more than just a

    5457 Gemgold Ct, Windermere, FL 34786
  • /6

    $1,475 Per Month

    • 1 Bed
    • 1 Bath
    • 400 Sq Ft
    • Unit ADU

    13841 Ancilla Blvd, Windermere, FL 34786

    This property is available. Please inquire on this site to schedule a showing. Discover a charming ADU located at 13841 Ancilla Blvd, Windermere, FL 34786. This delightful property offers a seamless blend of comfort and functionality, perfect for those seeking a cozy and convenient living space. The exterior features a well-maintained facade with a spacious garage, ensuring ample parking

    Unit ADU

    13841 Ancilla Blvd, Windermere, FL 34786
  • /15

    $2,475 Per Month

    • 4 Beds
    • 3 Baths
    • 1,736 Sq Ft
    • Condo for Rent

    12060 Via Caselli Ln, Windermere, FL 34786

    This well-maintained townhouse at 12060 Via Caselli Ln offers 1736 square feet of modern suburban living with four bedrooms and three bathrooms. Its light blue exterior with white trim and a covered porch create an inviting curb appeal, perfectly situated on a street corner for added privacy. Inside, neutral tones and contemporary finishes define the open living spaces, highlighted by tile

    12060 Via Caselli Ln, Windermere, FL 34786
  • /20

    $2,570 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,668 Sq Ft
    • House for Rent

    8831 Herencia Aly, Windermere, FL 34786

    Welcome to 8831 Herencia Aly, a charming 3-bedroom, 2.5-bath residence boasting 1,668 square feet of living space. You will surely appreciate the inviting layout of the home, featuring elegant tile flooring, soothing neutral paint, and a generous living and dining area flooded with natural light. The well-appointed kitchen showcases ample countertops, wooden cabinets, tile backsplashes, and

    8831 Herencia Aly, Windermere, FL 34786
  • /20

    $2,450

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft
    • Townhouse for Rent

    11565 Mizzon Dr, Windermere, FL 34786

    Upscale condo in Windermere. Third floor unit but elevator is available. Freshly painted, new carpets in bedrooms and wood floors in main living area. Screened patio. Split bedrooms. Community pool and fitness and walking distance to restaurants and shops

    11565 Mizzon Dr, Windermere, FL 34786
  • /23

    $9,500 Per Month

    • 5 Beds
    • 7 Baths
    • 5,205 Sq Ft
    • House for Rent

    11406 Waterstone Loop Dr, Windermere, FL 34786

    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.

    Kimroy Mussington WEICHERT REALTORS HALLMARK PRO

    11406 Waterstone Loop Dr, Windermere, FL 34786
  • /2

    $2,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,979 Sq Ft
    • Townhouse for Rent

    13743 Bravante Aly, Windermere, FL 34786

    Beautiful 3-bedroom, 2.5-bath townhome available for rent in the desirable Vineyards community of Windermere. This spacious two-story home offers approximately 1,996 sq. ft. with an open-concept layout, modern finishes, and comfortable living spaces.The first floor features a bright living and dining area, a well-appointed kitchen with stainless steel appliances, ample cabinet and counter space,

    13743 Bravante Aly, Windermere, FL 34786
  • /58

    $3,900 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,696 Sq Ft
    • House for Rent

    13544 Riggs Way, Windermere, FL 34786

    Welcome to this beautifully updated home in the highly desirable Enclave at Berkshire Park in Windermere. Situated on an oversized corner lot of approximately .25 acres, this spacious residence offers the perfect combination of comfort, functionality, and curb appeal. Recently refreshed with brand-new interior paint and new carpet throughout, the home also features a newer roof and a spacious

    Evan Caulfield STOCKWORTH REALTY GROUP

    13544 Riggs Way, Windermere, FL 34786
  • /2

    $2,650 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,480 Sq Ft
    • Stunning 3/2.5 corner townhome in Lake Reams with 2 car garage! Available mid July!

    8832 Danforth Dr, Windermere, FL 34786

    Stunning 3-bedroom, 2.5-bath corner townhome in Lakes of Windermere available in July. This two-story home features a rear-entry 2-car garage, wood-look tile on the first floor, and carpeted bedrooms on the second floor. The spacious open floor plan and stainless steel kitchen appliances create an inviting living space. The 2nd floor laundry facility located next to the bedrooms makes laundry a

    8832 Danforth Dr, Windermere, FL 34786
  • /47

    $4,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 3,472 Sq Ft
    • House for Rent

    13272 Penshurst Ln, Windermere, FL 34786

    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.

    Donny Hang Fung BLUEHOUSE REALTY GROUP LLC

    13272 Penshurst Ln, Windermere, FL 34786
  • /15

    $2,100 Per Month

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft
    • Townhouse for Rent

    8256 Maritime Flag St, Windermere, FL 34786

    3 Bedroom 2 Bath First Floor Condo in the gated community of Lakeside at Windermere. Large open Floor plan with Dinning Room, Family Room and Kitchen. Screened in patio. Master Bedroom has attached Bathroom with double vanity, large soaking tub and walk in closet. Club House with Fitness Center, 2 Pools, Sand Volleyball Court and outdoor BBQ areas. 2 Additional Bedrooms with large closets share a

    8256 Maritime Flag St, Windermere, FL 34786
  • /20

    $3,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft
    • House for Rent

    6526 Golden Dewdrop Trail, Windermere, FL 34786

    Beautiful rental home in the desirable **Windermere Landing** community! This freshly painted 2-story home offers approximately **2,139 sq. ft.**, featuring **3 bedrooms, 2.5 bathrooms, and a 2-car garage**. The home has a bright **open-concept layout**, spacious living and dining areas, and a functional kitchen with **granite countertops** and plenty of cabinet space. Bathrooms also feature

    Sergio Duarte FLORIDA LEGACY REALTY LLC

    6526 Golden Dewdrop Trail, Windermere, FL 34786
  • /8

    $8,500 Per Month

    • 4 Beds
    • 3 Baths
    • 3,244 Sq Ft
    • House for Rent

    6119 Foxfield Ct, Windermere, FL 34786

    Explore luxurious living in this modern Keenes Pointe rental home, seamlessly blending elegance and comfort. Embrace the picturesque views of the golf course from your backyard. Recently updated with tasteful tile throughout, the interior boasts three bedrooms on the first floor, including a master suite and a spacious office. The second floor features a large bedroom with a walk in closet and a

    6119 Foxfield Ct, Windermere, FL 34786
  • /26

    $2,550 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,492 Sq Ft
    • Townhouse for Rent

    13431 Carroway St, Windermere, FL 34786

    Great opportunity to live in a very desirable area. Great schools and conveniently located. Features SS appliances and stone counter tops in the kitchen. Has laminate flooring throughout the main areas and bedrooms. Master bedroom is on the ground floor. Washer and dryer are included. Two car garage. Don't miss out!

    Maria Milanes PRIME USA REALTY LLC

    13431 Carroway St, Windermere, FL 34786
  • /41

    $2,850 Per Month

    • 3 Beds
    • 2 Baths
    • 1,866 Sq Ft
    • House for Rent

    8556 Greenbank Blvd, Windermere, FL 34786

    Come view this 3 bed/2 bath Windermere home located in the gated community of The Preserve at the Lakes of Windermere! Inside, you'll find crown molding, wainscoting, vaulted ceilings, plenty of natural light, and tile floors throughout the home! The open kitchen is equipped with stainless steel appliances, a subway tile backsplash, quartz countertops, an island, and a pantry closet.

    8556 Greenbank Blvd, Windermere, FL 34786
  • /42

    $15,950 Per Month

    • 6 Beds
    • 8 Baths
    • 6,881 Sq Ft
    • House for Rent

    3999 Isabella Cir, Windermere, FL 34786

    Exquisite Luxury Retreat in Prime Windermere Location Welcome to 3999 Isabella Cir, an architectural masterpiece nestled within the prestigious community of Casabella at Windermere, FL. This opulent estate is a true embodiment of refined living, offering a harmonious blend of elegant design, impeccable craftsmanship, and unparalleled comfort. Situated on an expansive half acre lot, this

    Lucas DeSouza DELUCA REAL ESTATE SERVICES CORP

    3999 Isabella Cir, Windermere, FL 34786
  • /15

    $2,850 Per Month

    • 3 Beds
    • 2 Baths
    • 1,492 Sq Ft
    • House for Rent

    9142 Sabal Palm Cir, Windermere, FL 34786

    For Rent 9142 Sabal Palm Circle, Windermere, FLDeposit: $2850 Rent: $2850Contact Polina Korbutiak at or email to schedule your private showing. Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been established.Beautiful 3-bedroom, 2-bath pool home featuring an open floor plan, updated kitchen

    9142 Sabal Palm Cir, Windermere, FL 34786
  • /20

    $2,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,569 Sq Ft
    • Townhouse for Rent

    11933 Water Run Aly, Windermere, FL 34786

    Welcome to Ashlin Park, one of Windermere’s most sought-after communities! This beautifully maintained 3-bedroom, 2.5-bath townhome offers the perfect blend of style, comfort, and convenience. Built in 2016, the home features an open-concept floor plan filled with natural light, upgraded finishes, stainless steel appliances, and a private courtyard ideal for relaxing or entertaining. A detached

    Brynn Munro CORCORAN PREMIER REALTY

    11933 Water Run Aly, Windermere, FL 34786
  • /10

    $2,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,460 Sq Ft
    • House for Rent

    8265 Maritime Flag St, Windermere, FL 34786

    Now Leasing: 3BR/2.5BA Townhome in Amenity-Rich Lakeside Community - Just Minutes from Disney!This beautiful 3-bedroom, 2.5-bath townhome is officially on the market and won't last long. Located in the highly desirable, amenity-rich Lakeside community, this gated property offers the perfect blend of comfort, convenience, and lifestyle.The monthly rent includes water and access to

    8265 Maritime Flag St, Windermere, FL 34786
  • /27

    $2,750 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,547 Sq Ft
    • Townhouse for Rent

    9031 Legado Dr, Windermere, FL 34786

    Beautiful two-story home with stunning lake views in the desirable Legado community! This well-maintained residence features 3 spacious bedrooms, 2 full bathrooms, and 1 half bath, offering comfort and functionality in an excellent location. Enjoy a charming front entry with a landscaped garden and a private outdoor space overlooking the lake — perfect for relaxing and enjoying the view. The home

    Moniele Coelho WRA BUSINESS & REAL ESTATE

    9031 Legado Dr, Windermere, FL 34786
  • /9

    $4,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,871 Sq Ft
    • 5 Bedroom at West side Village at Heart of Windermere

    13024 Westside Vlg Lp, Windermere, FL 34786

    Located in the highly desirable heart of Windermere, Westside Village is only minutes from access to multiple lakes, dining, shopping, and A-rated schools. Westside Village will also have fantastic community amenities including a resort-style pool, clubhouse, and playground. energy-efficient home feature open floor plan. Enjoy cooking meals in the open kitchen overlooking the family room.

    13024 Westside Vlg Lp, Windermere, FL 34786
  • /15

    $2,700 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,614 Sq Ft
    • Townhouse for Rent

    7283 Penkridge Ln, Windermere, FL 34786

    New AC Installed.Freshly painted house.Some appliances are new. Beautiful townhouse located in the highly desirable Windermere Sound community in Windermere. Welcome to this beautifully maintained 3 bedroom, 2.5 bathroom townhouse offering the perfect blend of comfort, style, and convenience. Perfect for relaxing or entertaining. Step inside to find gorgeous ceremic tiles and an open living

    Monza Adnan OLYMPUS EXECUTIVE REALTY INC

    7283 Penkridge Ln, Windermere, FL 34786
  • /28

    $3,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,903 Sq Ft
    • Move-in Ready Home with 2 Car Garage in Desirable Summerport Community!

    5007 River Gem Ave, Windermere, FL 34786

    Welcome to the perfect rental home in the desirable community of Summerport! This home has it all as it sits on a corner lot, has both a front porch and screened-in back porch, fully fenced in lush backyard (lawn care included!) with paver patio and much more! Inside you're greeted by what could be a formal living room or dining room space and from there enter the fully loaded kitchen with LG

    5007 River Gem Ave, Windermere, FL 34786
  • /25

    $3,100 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,970 Sq Ft
    • House for Rent

    12784 Garridan Ave, Windermere, FL 34786

    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

    Jacky Liu YORK MILLS REALTY LLC

    12784 Garridan Ave, Windermere, FL 34786
  • /26

    $3,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,611 Sq Ft
    • House for Rent

    7329 Auburnwood Ln, Windermere, FL 34786

    Beautiful property with 4 bedrooms , 2 bath and 1/2 bathrooms , Windermere area.Just 5 minutes from Walt Disney World theme parks .

    7329 Auburnwood Ln, Windermere, FL 34786
  • /51

    $2,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,642 Sq Ft
    • Townhouse for Rent

    14392 Bridgewater Crossings Blvd, Windermere, FL 34786

    Location, Location, Location! Amazing 3 bedroom 2.5 bath, 2 story townhome located directly accross the street from the park in Summerport! Windermere!! Super clean, updated townhouse. Wood floors throughout. Stainless Steel appliances. Master is on the bottom floor. Second floor features a loft, as well as 2 bedrooms and a bathroom. 2 car rear entry garage. Sit back on your front porch with your

    Aleem Kanji CROWN REALTY COMPANY

    14392 Bridgewater Crossings Blvd, Windermere, FL 34786
  • /15

    $2,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,116 Sq Ft
    • House for Rent

    11686 Water Run Aly, Windermere, FL 34786

    Welcome to this beautiful and well-maintained 3-bedroom, 2.5-bathroom townhome, located in one of Windermere's most desirable communities. Offering the perfect blend of comfort, style, and convenience, this home is ideal for families and professionals alike.The spacious open floor plan features a bright living and dining area that flows seamlessly into a stunning gourmet kitchen with

    11686 Water Run Aly, Windermere, FL 34786
  • /37

    $12,500 Per Month

    • 3 Beds
    • 3 Baths
    • 3,535 Sq Ft
    • House for Rent

    9701 Lake Isleworth Ct, Windermere, FL 34786

    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

    Michelle Corbin ISLEWORTH REALTY LLC

    9701 Lake Isleworth Ct, Windermere, FL 34786
  • /8

    $1,300 Per Month

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Townhouse for Rent

    12645 Salomon Cove Dr, Windermere, FL 34786

    1/1 guest house above the garage for rent, included HOA, lawn care, shared internet, garage is not included, one parking spot. Close to shopping center and Disney parks. requirement, income 3X of rent, good credit. NO PETS.

    12645 Salomon Cove Dr, Windermere, FL 34786
  • /90

    $5,500 Per Month

    • 6 Beds
    • 4 Baths
    • 4,176 Sq Ft
    • House for Rent

    8278 Procida Isle Ln, Windermere, FL 34786

    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,

    Li Xue AGENT GROUP REALTY

    8278 Procida Isle Ln, Windermere, FL 34786
  • /2

    $2,095 Per Month

    • 2 Beds
    • 2 Baths
    • 1,161 Sq Ft
    • 8264-1429 Maritime Flag st. Condo

    8264 Maritime Flag St, Windermere, FL 34786

    CONDO - Newly renovated. 2 bed/2 bath, NEW Floors, New carpet in bedrooms, New paint throughout. Beautiful balcony, Elevator to 3rd floor. Nice Community amenities.

    8264 Maritime Flag St, Windermere, FL 34786
  • /33

    $3,100 Per Month

    • 4 Beds
    • 3 Baths
    • 2,190 Sq Ft
    • House for Rent

    8625 Greenbank Blvd, Windermere, FL 34786

    Single family home with 4 bedrooms and 3 full bathrooms in desirable Lakes of Windermere Peachtree subdivision. This is quaint community convenient to Disney attractions for work or play and is gated and zoned for Windermere High School. Available just in time for the new school year. Located on a scenic pond w conservation area view, with no rear neighbors and uninhibited views of the

    Charles Woolley BHHS FLORIDA REALTY

    8625 Greenbank Blvd, Windermere, FL 34786

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Why Live in Windermere

Windermere, Florida, is a small town known for its Old Florida charm and scenic setting on the Butler Chain of Lakes. It celebrated its centennial in 2025, and features quiet, walkable streets shaded by loblolly pines and live oaks draped with Spanish moss. The community is family-friendly, with highly rated public and private schools, including Windermere Elementary, Bridgewater Middle, Windermere High and Windermere Preparatory Academy. Windermere is composed of multiple subdivisions, many gated, with homes ranging from Mediterranean and French Provincial estates in Isleworth to Colonial Revivals and Contemporary styles in other developments. Townhomes and condos are also available in communities like Lake Burden and the Lakes of Windermere. The town offers various amenities, including the Windermere Recreation Center, Town Square Park, and private clubs like Isleworth Golf & Country Club. Residents enjoy local events such as the Windermere Wine & Dine and the weekly Windermere Farmer’s Market. Main Street features locally owned shops and dining options, while the nearby Grove shopping center and Dr. Phillips Restaurant Row provide additional choices. Windermere is conveniently located less than 15 miles from Orlando’s major attractions, hospitals, and about 25 miles from Orlando International Airport.

Frequently Asked Questions

How much does it cost to rent a home in Windermere, FL?
The median rent for a home in Windermere, FL is $2,900 per month, though prices vary by neighborhood, size, and property type. As of July 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Windermere, FL?
To comfortably afford the median rent in Windermere, FL, a household needs to earn roughly $116,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $2,900 per month in Windermere, FL, renters typically need to show $8,700 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Windermere, FL?
In Windermere, FL, the price-to-rent ratio is 23.9, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Windermere, FL are best for renting a home?
The best neighborhood for renting in Windermere, FL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include Lake Tibet, Bay Hill, MetroWest, West Oaks and Universal, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
86
Median Rent
$2,900
Median Single Family Home Rent
$3,500
Median Townhouse Rent
$2,550
Median Condo Rent
$2,125
How to Rent a Home