29

Windermere, FL Homes for Rent with Private Pool

Section Image
  • /3

    $3,200 per month

    • 4 Beds
    • 3 Baths
    • 2,551 Sq Ft
    • House for Rent

    11032 Belmere Isles Ct, Windermere, FL 34786

    Beautiful 4 bedroom, 3 bath home located within guard gated community of the Reserves of Belmere. Screened in pool overlooking pond. Eat in kitchen. Two car garage. Located on cud-a-sac. Come see!

    Barbara Schafer Holland CLASSIC INTERNATIONAL REALTY LLC

    11032 Belmere Isles Ct, Windermere, FL 34786
  • /21

    $4,200 per month

    • 4 Beds
    • 2 Baths
    • 2,516 Sq Ft
    • House for Rent

    13351 Zori Ln, Windermere, FL 34786

    ..... Available on July 1, 2025..... One of the rare find pool home in the desirable Providence community in Windermere. Freshly painted interior. Walking distance to Windermere High School, Windermere Preparotary School, Restaurant, and Grocery shopping. Tile in all common areas and wood floor in all bedrooms. Lawn and pool maintenance are included in the monthly rent. This house is zoned for

    Jennie Ho MAY HO REALTY

    13351 Zori Ln, Windermere, FL 34786
  • /39

    $12,000 per month

    • 5 Beds
    • 4.5 Baths
    • 4,417 Sq Ft
    • House for Rent

    5001 Latrobe Dr, Windermere, FL 34786

    Available for immediate occupancy. This beautiful, traditional five-bedroom pool home is on a quiet cul-de-sac in Isleworth, Windermere. The traditional brick exterior, grand French doors, and warm mahogany wood floors invite friends and family home. Enjoy views of majestic oaks, the 7th fairway, and Lake Bessie on this half-acre lot. This two-story home is perfect for entertaining and easy to

    Laura Diss Q BOUTIQUE SPECIALTY REALTY INC

    5001 Latrobe Dr, Windermere, FL 34786
  • /14

    $3,450 per month

    • 3 Beds
    • 2 Baths
    • 1,948 Sq Ft
    • House for Rent

    7530 Colbury Ave, Windermere, FL 34786

    Look no further ! Paradise has been found poolside at your house , located in a corner lot with amazing conservation view and privacy . This beautiful house 3 bedroom and 2 bath , 2car garage ready to move in only tile in the wet areas and carpet on the Rooms . You will enjoy the views of the conservation area in the back of the house. There’s much appreciate about this house that you must see it

    Carlos Lopez Sotomayor RESOURCE ONE REALTY

    7530 Colbury Ave, Windermere, FL 34786
  • /64

    $19,000 per month

    • 6 Beds
    • 5.5 Baths
    • 7,971 Sq Ft
    • House for Rent

    4260 Isabella Cir, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Welcome to 4260 Isabella Circle, nestled in the heart of scenic Windermere, FL. This exceptional residence blends luxury, comfort, and convenience. Located in a tranquil and upscale community, you’ll enjoy close proximity to top-rated schools, shopping centers, fine dining, parks, and more.Step inside to experience an expansive open layout

    Julimar Barreiro Pastrana SERHANT

    4260 Isabella Cir, Windermere, FL 34786
  • /37

    $4,500 per month

    • 5 Beds
    • 3 Baths
    • 3,255 Sq Ft
    • House for Rent

    2012 Willow Lauren Ln, Windermere, FL 34786

    Nestled in the heart of The Willows at Lake Rhea, this breathtaking 5-bedroom, 3 bath POOL home sits on a spacious .61-Acre Cul-De-Sac lot. with the perfect amount of space, updates; and an exceptionally well established neighborhood 2012 WILLOW LAUREN LN, WINDERMERE, FL 34786 offers tons of space, privacy, presence, with matured landscaping, and an expansive driveway, leading to your 3-car

    Ricardo Diaz WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC

    2012 Willow Lauren Ln, Windermere, FL 34786
  • /13

    $6,900 per month

    • 5 Beds
    • 5.5 Baths
    • 3,607 Sq Ft
    • House for Rent

    1232 Glenheather Dr, Windermere, FL 34786

    Gorgeous home in a gated community. High ceilings and luxury vinyl planks all over the house. This house has two primary bedrooms, one located on the first floor and the other on the second floor; both primary bathrooms are done in very light marble, making them feel airy and bright. There is also an extra suite on the first floor, very convenient for guests and two extra bedrooms on the second

    Marilene Auge CHARLES RUTENBERG REALTY ORLANDO

    1232 Glenheather Dr, Windermere, FL 34786
  • /26

    $6,000 per month

    • 4 Beds
    • 3 Baths
    • 2,830 Sq Ft
    • House for Rent

    2113 Grove Point Ln, Windermere, FL 34786

    Discover this stunning rental home located in the Waterford Pointe community on Lake Roberts. Enjoy exclusive access to a private community boat ramp in a serene, gated neighborhood.This beautifully furnished residence features new bamboo flooring, high-end appliances, and elegant décor throughout. Designed for year-round Florida living, the home includes a private in-ground pool, spa, and an

    Alexandra Costa Thomas THE FLORIDA LOUNGE REALTY LLC

    2113 Grove Point Ln, Windermere, FL 34786
  • /98

    $39,500 per month

    • 7 Beds
    • 10 Baths
    • 8,362 Sq Ft
    • House for Rent

    9343 Tibet Pointe Cir, Windermere, FL 34786

    Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completely updated. The modern exterior color brightens the façade and creates a unique transitional style. The wrought iron and glass doors add a refined entry. Opening to the two-story formal areas featuring timeless elements of stone flooring, elegant ceiling details,

    Juan Delgado LA ROSA REALTY LLC

    9343 Tibet Pointe Cir, Windermere, FL 34786
  • /11

    $10,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,452 Sq Ft
    • House for Rent

    6449 Cartmel Ln, Windermere, FL 34786

    - This home has been completely transformed. The elegant European architectural style custom estate is perfectly sited on an oversized homesite in guard-gated Lake Butler Sound. Upon entering the house, the light from the windows and French doors visually links the formal areas. The updated gourmet kitchen offers a spacious setting for casual meals. The area offers convenience with exotic stone

    Marilu Ravelo AMERICAN INTERNATIONAL REALTY

    6449 Cartmel Ln, Windermere, FL 34786
  • /14

    $9,000 per month

    • 4 Beds
    • 2.5 Baths
    • 3,200 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

    Hans Welbergen WINDERMERE INTERNATIONAL REALTY

    6119 Foxfield Ct, Windermere, FL 34786
  • /29

    $6,500 per month

    • 4 Beds
    • 3 Baths
    • 2,795 Sq Ft
    • House for Rent

    8374 Bowden Way, Windermere, FL 34786

    This house is located in Keene's Pointe Community in Windermere, 24-hours guard-gated community, the Jack Nicklaus designed Golf course Community. Playgrounds, boat ramp and beautiful walking areas, Close to shopping, restaurants and minutes from Disney. This spacious corner lot house, one story, offers 4 bedrooms and 3 baths plus a private office . The kitchen and family room are open and

    Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

    8374 Bowden Way, Windermere, FL 34786
  • /17

    $8,500 per month

    • 4 Beds
    • 5.5 Baths
    • 4,629 Sq Ft
    • House for Rent

    5723 Oxford Moor Blvd, Windermere, FL 34786

    For lease is a breathtaking dream home in Oxford Moor. This Windermere luxurious gated community is an upscale neighborhood with Mediterranean style million dollar houses, picturesque lake with a fountain and tennis court. This house's beautiful landscape was professionally designed and meticulously maintained. The owner takes so much pride of this 0.6 acre of outdoor paradise that the lawn

    Hans Welbergen WINDERMERE INTERNATIONAL REALTY

    5723 Oxford Moor Blvd, Windermere, FL 34786
  • /25

    $5,800 per month

    • 6 Beds
    • 4 Baths
    • 3,577 Sq Ft
    • House for Rent

    13932 Florigold Dr, Windermere, FL 34786

    Welcome to paradise in the heart of Summerport! This exquisite 6 bedroom, 4 full bathroom pool home offers an abundance of amenities and is nestled in the tranquil, gated community of Eden's Isle, and scenic views of Lake Speer. Situated along Lake Speer's canal, residents of this esteemed community enjoy exclusive access to a private boat ramp, perfect for leisurely days on the water. With over

    Melissa Becorest RE/MAX TITANIUM GROUP

    13932 Florigold Dr, Windermere, FL 34786
  • /63

    $15,000 per month

    • 5 Beds
    • 4.5 Baths
    • 4,345 Sq Ft
    • House for Rent

    4279 Isabella Cir, Windermere, FL 34786

    Welcome to 4279 Isabella Cir, Windermere, FL 34786. Offered as a lease with an option to purchase. This 5-bedroom, 4/2-bathroom home has been completely remodeled and upgraded, perfectly marrying luxury with comfort. As you enter, you are greeted by an impressive formal living room with 30’ ceilings and two stories of windows that offer a stunning view of the sparkling swimming pool. Within the

    John Silva JOHN SILVA REALTY & ASSOCIATES

    4279 Isabella Cir, Windermere, FL 34786
  • /60

    $6,299 per month

    • 4 Beds
    • 3 Baths
    • 2,128 Sq Ft
    • House for Rent

    9037 Ron Den Ln, Windermere, FL 34786

    Includes a separate apartment ! Fully furnished and fully renovated Windermere home that captures the essence of Bali with a water fountain, Lakeview and deeded lake access . Live at a retreat while being minutes from restaurants and shopping ! Full apartment in the back with a pergola and quiet space separate from Main house . Beautiful brick paver driveway and a resort style pool with a

    Natalie Citarelli CITARELLI REALTY GROUP LLC

    9037 Ron Den Ln, Windermere, FL 34786
  • /33

    $12,700 per month

    • 6 Beds
    • 6 Baths
    • 5,667 Sq Ft
    • House for Rent

    13515 Bellaria Cir, Windermere, FL 34786

    Must see, luxury home! Very rare property of its size available for rent in prestigious Windermere. This 2-story, 6 bedroom, 6 bath triple car garage home features a great room with marble fireplace, over-sized windows facing the rear deck & resort style pool, has a heated spa and pool. The pool is the dramatic focal point of the main level, accompanied by a formal dining room. Chef's kitchen,

    Jessica Martinez Cestero HAMPTON & HAMPTON MGMT LEASING

    13515 Bellaria Cir, Windermere, FL 34786
  • /44

    $8,500 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, a beautifully appointed 5-bedroom, 4.5-bathroom home located in the highly sought-after, family-friendly community of Lake Cypress Cove in Windermere, FL. With over 4,000 square feet of thoughtfully designed living space on more than half an acre, this home offers the perfect blend of luxury and comfort for your growing family. The open floor plan creates a warm and

    Charles Newman UNITED REALTY GROUP INC

    6020 Marleon Dr, Windermere, FL 34786
  • /33

    $8,995 per month

    • 4 Beds
    • 3.5 Baths
    • 3,751 Sq Ft
    • House for Rent

    6533 Cartmel Ln, Windermere, FL 34786

    One or more photo(s) has been virtually staged. AUTHENTIC MEDITERRANEAN ELEGANCE IN WINDERMERE! This beautiful 4 bedroom/3.5 bath single story pool home has everything a discerning tenant is looking for in a rental residence. Drive through the fountained 24-hour guard gated front entrance of Reserve at Lake Butler Sound and take notice of the winding tree lined street that leads you to the

    Mary Currie BHHS FLORIDA REALTY

    6533 Cartmel Ln, Windermere, FL 34786
  • /15

    $12,000 per month

    • 5 Beds
    • 5.5 Baths
    • 4,421 Sq Ft
    • House for Rent

    5023 Sawyer Cove Way, Windermere, FL 34786

    Experience refined modern living at 5023 Sawyer Sound Way, a luxury home in Windermere. This thoughtfully crafted residence features 5 bedrooms, 5.5 bathrooms, expansive living spaces, and an open-concept floor plan filled with natural light. Clean lines and warm, textured finishes create a soft, welcoming feel rarely found in modern architecture. Enjoy a chef’s kitchen, seamless indoor-outdoor

    Gordy Singh FLORIDA HOME FINDERS

    5023 Sawyer Cove Way, Windermere, FL 34786
  • /48

    $7,200 per month

    • 4 Beds
    • 4 Baths
    • 3,717 Sq Ft
    • House for Rent

    8556 Bowden Way, Windermere, FL 34786

    Located in KEENE'S POINTE GATED GOLF COMMUNITY! This one will not last! This home is immaculate and the very definition of luxury living. It was completely renovated in 2018 along with a BRAND NEW ROOF in May 2022. As you walk in from the gorgeous entry way you'll immediately feel the elegance. The stunning dining room with a beautiful chandelier is to the immediate right. To the left is a very

    Ryan Scotson ICON REALTY ASSOCIATES INC

    8556 Bowden Way, Windermere, FL 34786
  • /41

    $4,500 per month

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

    8719 Crescendo Ave, Windermere, FL 34786

    Breathtaking POOL House at the desirable Windermere Trails. This elegantly FURNISHED house features a spacious kitchen with SS appliances, large center island, walk in pantry, granite countertops with tile backsplash and eat in dining all open to Family room, overlooking your private lanai and Pool. The main level Master suite has a huge walk in closet and spa like bath with his and hers sinks

    Maria Ubillus FOLIO REALTY LLC

    8719 Crescendo Ave, Windermere, FL 34786
  • /53

    $12,500 per month

    • 4 Beds
    • 4.5 Baths
    • 4,013 Sq Ft
    • House for Rent

    6036 Greatwater Dr, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Welcome to Keene’s Pointe! Discover the charm of this custom-built home located on the 17th Fairway of the renown Jack Nicklaus Signature Golf Course and across from the lakefront mansions that line this quiet cul-de- sac on Greatwater Drive. This 4BR/4Full Bath/1 Half Bath golf course home exudes warmth from the gorgeous hardwood floors and

    Angela Durruthy KEENE'S POINTE REALTY

    6036 Greatwater Dr, Windermere, FL 34786
  • /100

    $4,300 per month

    • 4 Beds
    • 3 Baths
    • 3,114 Sq Ft
    • House for Rent

    13461 Zori Ln, Windermere, FL 34786

    NEW PICTURES COMING SOON. THIS HOME IS GETTING A NEW FACE LIFT INSIDE NEW PAINT,COUNTERTOP, LIGHTER FLOORING, CARPET IN THE THEATER ROOM AND MORE.This stunning 4-bedroom, 3-bathroom home for rent is located in the desirable Windermere community, just minutes away from the newly built Windermere High School. With a spacious and elegant floor plan, this home offers a luxurious living experience.

    Courtney James LA ROSA REALTY ORLANDO LLC

    13461 Zori Ln, Windermere, FL 34786
  • /49

    $6,450 per month

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

    307 W 4th Ave, Windermere, FL 34786

    Executive rental pool home located in the charming town of Windermere! The location is just two block from Main st and all that downtown Windermere has to offer! This single-story, 4-bedroom (2 primary bedrooms), 3-bathroom home, sits on an oversized corner lot in the shade of majestic oak trees. Enjoy a gourmet kitchen featuring stainless steel appliances, two brand new refrigerators, a

    Katie Bray MAINFRAME REAL ESTATE

    307 W 4th Ave, Windermere, FL 34786
  • /43

    $13,500 per month

    • 3 Beds
    • 3 Baths
    • 3,247 Sq Ft
    • House for Rent

    9742 Green Island Cove, Windermere, FL 34786

    Nestled along the shores of beautiful Lake Louise within the gates of Isleworth Golf & Country Club, this charming golf villa offers a prime lakefront location in proximity to the Clubhouse. The interior boasts more than 3,000 square feet of living space, with an open floor plan set against a backdrop of picturesque water views. Elegant hardwood floors travel throughout the single-story floor

    Monica Lochmandy ISLEWORTH REALTY LLC

    9742 Green Island Cove, Windermere, FL 34786
  • /25

    $9,500 per month

    • 4 Beds
    • 3.5 Baths
    • 4,097 Sq Ft
    • House for Rent

    9525 Lavill Ct, Windermere, FL 34786

    Located on Lake Down of the Butler Chain of Lakes lies this custom-built 4 bed, 3.5 bath, 4,097 square foot pool home. Sitting on two acres with southern lakefront exposure, enjoy spectacular views of both sunrise and sunset over Lake Butlers Chain of Lakes. Upon entering the home you are greeted to a wonderful view of the lake through the two story cathedral windows in the grand living area with

    John Goggin STOCKWORTH REALTY GROUP

    9525 Lavill Ct, Windermere, FL 34786
How to Rent a Home