34

Windermere, FL Houses for Rent with Community Pool

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  • /26

    $4,990 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,596 Sq Ft
    • House for Rent

    10914 Ledgement Ln, Windermere, FL 34786

    Stunning 4BR/3 full + 2 half bath rental in a gated Windermere community! Enjoy all-tile flooring throughout and your own private in-ground pool. Spacious, low-maintenance, and move-in ready — close to top schools, shopping, and dining. Schedule a showing today!

    Agent Photo

    Rohini Bandaru

    LA ROSA REALTY KISSIMMEE

    10914 Ledgement Ln, Windermere, FL 34786
  • /20

    $5,995 Per Month

    • 5 Beds
    • 5 Baths
    • 3,835 Sq Ft
    • House for Rent

    7231 Sangalla Dr, Windermere, FL 34786

    Property Id: 2781998 APPLICATION AND VERIFIABLE PROOF OF FUNDS/INCOME REQUIRED PRIOR TO SCHEDULING A PRIVATE SHOWING. Experience luxury living in the highly sought-after gated Casa Del Lago community in Windermere. This beautifully maintained 5-bedroom, 5 bath home offers 3,835 sq. ft. of spacious living with an open floor plan, primary suite on the first floor, private office, formal

    7231 Sangalla Dr, Windermere, FL 34786
  • /20

    $2,545 Per Month

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

    8831 Herencia Aly, Windermere, FL 34786

    SPLIT THE PAYMENT! Reserve your new home by paying 50% of your security deposit now, with the remaining balance due before move-in.Welcome to 8831 Herencia Alley in Windermere, FL (34786)! This modern two-story townhome offers 3 bedrooms, 2.5 bathrooms, and 1,668 square feet of bright, open living space in the sought-after Legado community. The main level features an open-concept layout

    8831 Herencia Aly, 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
  • /39

    $3,075 Per Month

    • 4 Beds
    • 3 Baths
    • 2,411 Sq Ft
    • House for Rent

    4468 Blue Major Dr, Windermere, FL 34786

    AVAILABLE NOW! Spacious 4-bedroom, 3-bath home in Windermere, located across from a neighborhood playground on a premium private lot with water views from the living room, kitchen, master bedroom, and bath. This single-story home features tile throughout the main living areas, Corian countertops, a large kitchen with 42" wood cabinetry, black appliances, a gas range, washer and dryer included,

    4468 Blue Major Dr, Windermere, FL 34786
  • /22

    $3,300 Per Month

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

    6526 Golden Dewdrop Trail, Windermere, FL 34786

    Welcome to 6526 Golden Dewdrop Trail, a freshly painted, move-in-ready home overlooking community green space with views toward the pool in desirable Windermere Landings. This inviting two-story residence offers approximately 2,139 square feet with 3 bedrooms, 2.5 bathrooms, a spacious upstairs loft, and a rear-entry 2-car garage. A covered front porch and second-floor balcony create attractive

    Sergio Duarte FLORIDA LEGACY REALTY LLC

    6526 Golden Dewdrop Trail, Windermere, FL 34786
  • /53

    $10,000 Per Month

    • 5 Beds
    • 4 Baths
    • 3,058 Sq Ft
    • House for Rent

    5927 Caymus Loop, Windermere, FL 34786

    Welcome to this exceptional 5Bed, 4Bath residence located in the highly desirable Keene’s Pointe community in Windermere. Situated on an oversized lot with beautiful views of the 14th fairway of the Jack Nicklaus Signature Golf Course, this home offers an impressive combination of space, comfort, and Florida living.The bright and spacious interior is filled with natural light and features

    Carla Renata Pereira Motta MS LAND & BUILDING LLC

    5927 Caymus Loop, Windermere, FL 34786
  • /44

    $2,950 Per Month

    • 4 Beds
    • 2 Baths
    • 2,300 Sq Ft
    • House for Rent

    12947 Runswick Ave, Windermere, FL 34786

    MOVE-IN READY! Beautiful and spacious 4-bedroom, 2-bath home located in the highly desirable Lakes of Windermere community. Surrounded by mature landscaping, scenic lakes, walking trails, and top-rated schools, this home even offers the opportunity to enjoy Disney fireworks just steps from your front door.This well-designed single-story home features luxury vinyl plank and tile flooring

    Cui Li RATIO REAL ESTATE, LLC

    12947 Runswick Ave, Windermere, FL 34786
  • /71

    $3,200 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,831 Sq Ft
    • House for Rent

    13831 Farella Aly, Windermere, FL 34786

    Your dream home in Windermere is waiting for you! This beautiful home features 4 bedrooms, 2.5 bathrooms, and a 2-car garage, offering the perfect combination of comfort and style. The spacious kitchen is equipped with granite countertops, complemented by matching granite in all bathrooms. The first floor features durable tile flooring throughout, creating a bright, open, and easy-to-maintain

    Maryelle Gama TALENT REALTY SOLUTIONS

    13831 Farella Aly, Windermere, FL 34786
  • /61

    $3,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,911 Sq Ft
    • House for Rent

    4718 Blue Major Dr, Windermere, FL 34786

    Move-in Ready. Landlord will provide brand-new washer and dryer.Welcome to 4718 Blue Major Drive, a beautifully maintained 3-bedroom, 2-bathroom residence offering 1,911 square feet of thoughtfully designed living space in the highly sought-after Windermere area. Move-in ready and exceptionally well cared for, this inviting home features fresh interior paint, a newer A/C system just two

    Jing Yue INTEREALTY SERVICE

    4718 Blue Major Dr, Windermere, FL 34786
  • /20

    $4,800 Per Month

    • 4 Beds
    • 3 Baths
    • 2,484 Sq Ft
    • House for Rent

    8794 Crescendo Ave, Windermere, FL 34786

    Stunning 4-bedroom, 3-full-bath home with a private pool in the highly sought-after Windermere Trails community! Built in 2016, this spacious home offers approximately 2,484 SF of beautifully designed living space with an open-concept floor plan, abundant natural light, and modern finishes throughout.The gourmet kitchen features quartz countertops, stainless steel appliances, ample cabinetry,

    Alessandra Oliveira FLORIDA CONNEXION PROPERTIES

    8794 Crescendo Ave, Windermere, FL 34786
  • /30

    $8,500 Per Month

    • 5 Beds
    • 5.5 Baths
    • 5,312 Sq Ft
    • House for Rent

    13503 Lake Cawood Dr, Windermere, FL 34786

    5 Bed 6 bath custom single family home in gated community. 1.02 acre corner lot, with private basketball court and over-sized screened area with private pool and spa. Kitchen hookup outside. Hardwood and marble floors throughout, vaulted ceilings, fireplace in family room and master bedroom. Master bed has custom built-in walk-in closet, large spa tub, and large shower. Home features two second

    Nicholas Horton BANNER INT'L REAL ESTATE

    13503 Lake Cawood Dr, Windermere, FL 34786
  • /22

    $3,050 Per Month

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

    14205 Bridgewater Crossings Blvd, Windermere, FL 34786

    Enjoy the tranquility of the Summerport community surrounded by lakes and beautiful landscaping, located near attractions and main access roads in desirable Windermere. This Community offers a pool, lakes, playgrounds, tennis courts, a fitness center, and trails. This is a 4 bedrooms 2.5 bathrooms, two-story home with a rear 2- car garage, stainless steel appliances, Corian countertops, and new

    Lisa Ingram INGRAM REALTY SERVICES LLC

    14205 Bridgewater Crossings Blvd, Windermere, FL 34786
  • /33

    $2,995 Per Month

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

    8625 Greenbank Blvd, Windermere, FL 34786

    PRICE IMPROVEMENT FOR IMMEDIATE AVAILABILITY! 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

    Charles Woolley BHHS FLORIDA REALTY

    8625 Greenbank Blvd, Windermere, FL 34786
  • /30

    $3,950 Per Month

    • 3 Beds
    • 3 Baths
    • 2,224 Sq Ft
    • House for Rent

    8318 Vivaro Isle Way, Windermere, FL 34786

    PRICE IMPROVEMENT -NOW $3,950- MONTH .Exeptional rental opportunity .Discover this impeccable single-story residence in the sought-after gas community of Windermere Isle . This home features a premium whole-house water filtration system, ensuring clean, crisp, and safe water from every single faucet. This maintenance-free home features elegant ceramic title throughout completely( carpet free),

    Sandra Pardo WENDY MORRIS REALTY

    8318 Vivaro Isle Way, Windermere, FL 34786
  • /42

    $14,000 Per Month

    • 7 Beds
    • 5.5 Baths
    • 5,221 Sq Ft
    • House for Rent

    6219 Tiroco Way, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Welcome to luxury living in the guarded, gated community of Waterstone in Windermere, Florida. This exceptional residence at 6219 Tiroco Way blends elegance, comfort, and modern efficiency, featuring solar power and an impressive floor plan designed for both everyday living and entertaining.The home offers 7 bedrooms, 51⁄2 bathrooms, a media

    Ryan Solberg MAXLIFE REALTY LLC

    6219 Tiroco Way, Windermere, FL 34786
  • /36

    $2,950 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,092 Sq Ft
    • House for Rent

    11804 Silverlake Park Dr, Windermere, FL 34786

    Move-in ready! This beautiful 4-bedroom, 2.5-bathroom home has been freshly painted throughout and features no carpet! Tile flooring on the first floor and vinyl flooring in all bedrooms. Located in the highly desirable Windermere Trails community, the home is just minutes from Walt Disney World and within walking distance of Bay Lake Elementary School.The first floor offers a bright and

    Cui Li RATIO REAL ESTATE, LLC

    11804 Silverlake Park Dr, Windermere, FL 34786
  • /47

    $3,100 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,053 Sq Ft
    • House for Rent

    13013 Overstreet Rd, Windermere, FL 34786

    Welcome to one of the best opportunities in Windermere's highly sought-after Lakes of Windermere community! This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect combination of comfort, convenience, and the Florida lifestyle buyers are searching for. Step inside to discover a thoughtfully designed floor plan featuring spacious living areas, abundant natural light, and stylish

    Omar Andreasen SERHANT

    13013 Overstreet Rd, Windermere, FL 34786
  • /72

    $3,100 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,236 Sq Ft
    • House for Rent

    13786 Summer Harbor Ct, Windermere, FL 34786

    Virtually Staged. Available Now! This beautifully appointed 4-bedroom, 2.5-bath home offers comfort, style, and picturesque water views. Relax on the charming front porch and enjoy the tranquil waterfront setting. The first floor features an open-concept layout with a spacious family room, dining area, and a well-equipped kitchen boasting granite countertops, stainless steel appliances, abundant

    Deborah Garson DEBORAH E GARSON PA

    13786 Summer Harbor Ct, Windermere, FL 34786
  • /21

    $3,600 Per Month

    • 5 Beds
    • 3.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    6971 Nobleton Dr, Windermere, FL 34786

    Gorgeous 5 bedrooms 3.5 bathrooms home in the desirable location of Windermere. 4 bedrooms downstairs are perfect for family members. a large bonus room with a full bath above the garage which can be your teenager's room, guest room, mother-in-law suite... It has a private entrance from the garage which gives the privacy of the living. Fully upgraded kitchen with spectacular granite counters and

    Alice Wang FOURSQUARE REAL ESTATE

    6971 Nobleton Dr, Windermere, FL 34786
  • /43

    $5,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 3,725 Sq Ft
    • House for Rent

    8719 Crescendo Ave, Windermere, FL 34786

    Beautifully Furnished Pool Home in Desirable Windermere Trails! This spacious, fully furnished home features an open-concept floor plan with a gourmet kitchen offering stainless steel appliances, granite countertops, tile backsplash, a large center island, walk-in pantry, and dining area overlooking the family room and private screened pool. The first floor includes the luxurious primary suite, a

    Maria Ubillus FOLIO REALTY LLC

    8719 Crescendo Ave, Windermere, FL 34786
  • /44

    $8,900 Per Month

    • 5 Beds
    • 4.5 Baths
    • 4,028 Sq Ft
    • House for Rent

    6020 Marleon Dr, Windermere, FL 34786

    Welcome to 6020 Marleon Drive, an exceptional 5-bedroom, 4-bathroom residence offering over 4,000 square feet of beautifully designed living space in the highly sought-after, guard-gated community of Lake Cypress Cove in Windermere. Set on more than half an acre, this impressive home offers the space, privacy, and amenities to enjoy the best of Florida living. Inside, soaring ceilings and

    Charles Newman UNITED REALTY GROUP INC

    6020 Marleon Dr, Windermere, FL 34786
  • /40

    $3,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,148 Sq Ft
    • House for Rent

    8321 Greenbank Blvd, Windermere, FL 34786

    Move in Ready! Spacious 4 Bed + 3.5 Bath home situated along conservation area on quiet cul-de-sac in GATED Preserve at Lakes of Windermere. The nearly 3,150 sq/ft of living area features a beautiful kitchen w/ stainless steel appliances + eat-in island, and includes formal living and dining rooms as well. The primary suite is also located on the first level while the 3 guest bedrooms are

    Brian Lemay ROMAN REALTY GROUP, LLC

    8321 Greenbank Blvd, Windermere, FL 34786
  • /8

    $3,900 Per Month

    • 3 Beds
    • 2 Baths
    • 2,258 Sq Ft
    • House for Rent

    2630 Stanton Hall Ct, Windermere, FL 34786

    The Manors is a Great Neighborhood and next to Windermere Elementary School * Property can be leased short term if needed during renovations or waiting for another home to be built - Call for details and pricing

    Darrell Nunnelley VINTAGE REALTY GROUP LLC

    2630 Stanton Hall Ct, Windermere, FL 34786
  • /36

    $3,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,723 Sq Ft
    • House for Rent

    9508 Pine Terrace Ct, Windermere, FL 34786

    Recently renovated and move in ready, this beautiful and unique home is perfectly situated in the heart of Windermere. Enjoy unmatched convenience just 15 minutes from Walt Disney World, 15 minutes from Universal Studios, and 30 minutes from Orlando International Airport. Inside, the open concept design brings together the living, family, and dining areas, creating an ideal setting for both

    Carlos De Guevara REAL BROKER, LLC

    9508 Pine Terrace Ct, Windermere, FL 34786
  • /91

    $9,990 Per Month

    • 4 Beds
    • 3 Baths
    • 2,737 Sq Ft
    • House for Rent

    10355 Trout Rd, Orlando, FL 32836

    Exceptional single-story lakefront residence on 1.57 acres of beautifully landscaped, mature grounds offering privacy, exclusivity, and breathtaking water views. This home features custom finishes throughout, including wood beam ceilings, personalized flooring, and seamless indoor-outdoor living with expansive glass doors connecting the living, dining, and kitchen areas. The chef’s kitchen

    Any Alves WRA BUSINESS & REAL ESTATE

    10355 Trout Rd, Orlando, FL 32836
  • /30

    $7,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,562 Sq Ft
    • House for Rent

    8411 Woburn Ct, Windermere, FL 34786

    Welcome to this 4-bedroom, 3-bathroom home located on a quiet cul-de-sac in the guard-gated community of Keene's Pointe. Backing to the Tibet-Butler Preserve, this property offers peaceful conservation views and added privacy.Inside, you'll find a bright, open floor plan with plenty of natural light and tasteful updates throughout. The remodeled kitchen features modern cabinetry, granite

    Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

    8411 Woburn Ct, Windermere, FL 34786
  • /64

    $29,000 Per Month

    • 7 Beds
    • 7 Baths
    • 8,000 Sq Ft
    • House for Rent

    9725 Chestnut Ridge Dr, Windermere, FL 34786

    A rare opportunity to lease a beautifully renovated residence within Isleworth, offering exceptional space, privacy, comfort, and an elevated Central Florida lifestyle.Newly renovated and exceptionally private, this sophisticated Isleworth residence offers approximately 8,000 square feet of beautifully designed living space, combining refined luxury with the comfort and functionality of

    Dianna Desboyaux DOUGLAS ELLIMAN

    9725 Chestnut Ridge Dr, Windermere, FL 34786
  • /31

    $6,750 Per Month

    • 4 Beds
    • 3 Baths
    • 2,398 Sq Ft
    • House for Rent

    8507 Bowden Way, Windermere, FL 34786

    Virtually Staged. Beautiful single-story home in the highly desirable gated community of Keene’s Pointe! This 4-bedroom, 3-bath residence 2,398 square feet with a split floor plan, tile flooring throughout, full-home solar power, updated appliances, and a wine refrigerator.Enjoy your private pool with pool enclosure and fenced backyard overlooking the 440-acre Tibet-Butler Nature Preserve,

    Jessica Dessire Cueva PA CHARLES RUTENBERG REALTY ORLANDO

    8507 Bowden Way, Windermere, FL 34786
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    $7,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,578 Sq Ft
    • House for Rent

    8351 Bowden Way, Windermere, FL 34786

    Virtually Staged. Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled 4-bedroom, 3-bathroom Windermere residence offers an exceptional blend of timeless architecture, sophisticated finishes, and effortless Florida living. From the moment you enter, the light-filled interior welcomes you with soaring coffered ceilings, custom-laid wood-look tile

    John Goggin STOCKWORTH REALTY GROUP

    8351 Bowden Way, Windermere, FL 34786
  • /28

    $3,150 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,469 Sq Ft
    • House for Rent

    13314 Roxboro Rd, Windermere, FL 34786

    Roomy and Updated 4 bedrooms and 3 Bath in Berkshire Park Subdivision. Located across the street from the amazing community playground, pool and clubhouse amenities, providing a million-dollar view. Enjoy the pool without the responsibility of maintenance. Very spacious downstairs with beautiful Granite Kitchen and Nice Appliance package inc. Washer & Dryer. Kitchen is equipped with an Island and

    Charles Woolley BHHS FLORIDA REALTY

    13314 Roxboro Rd, Windermere, FL 34786
  • /25

    $3,500 Per Month

    • 5 Beds
    • 4.5 Baths
    • 2,874 Sq Ft
    • House for Rent

    1125 Lascala Dr, Windermere, FL 34786

    Mediterranean-style 5-bedroom, 4.5-bath residence offering 2,874 square feet in gated Belmere Village. The flexible two-story floor plan includes a first-floor bedroom adjacent to a full bath, ideal for use as a private home office, guest suite or multigenerational space. Upstairs, the spacious primary suite features crown molding and a large walk-in closet, along with three additional

    Charles Woolley BHHS FLORIDA REALTY

    1125 Lascala Dr, Windermere, FL 34786
  • /24

    $3,000 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. Fresh Painting. 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

    Jacky Liu YORK MILLS REALTY LLC

    12784 Garridan Ave, Windermere, FL 34786

Rental Home Trends

Number of Houses for Rent
34
Median Single Family Home Rent
$5,000
Median 3 Bedroom Single Family Home Rent
$3,250
Median 4 Bedroom Single Family Home Rent
$5,000
Median 5 Bedroom Single Family Home Rent
$5,995
How to Rent a Home