Windermere, FL Houses for Rent with Private Pool

Welcome to the famed Butler Chain of Lakes waterfront lifestyle! Experience luxury living with small town charm in this Town of Windermere residence boasting breathtaking water views with access to 12 connected lakes. Three of the four bedrooms offer lake views, two with sitting areas and one with access to the patio. You will enjoy the mesmerizing lake vistas from every angle. Step outside into

Rebekkah Warmus REVEL REALTY LLC

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

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

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

Experience luxury living at its finest in this stunning 5-bedroom, 5-bath custom estate located in Windermere’s highly sought-after guard-gated Bellaria community. Designed with timeless Tuscan elegance and modern sophistication, this exceptional residence offers every amenity for refined living and grand entertaining. Step inside to discover a chef’s dream kitchen outfitted with top-of-the-line

Marisa Falk THE AGENCY ORLANDO

Welcome to this elegant home with lots of upgrades! The home features tiled roof and stone front, heated salt water pool; new upscale vinyl pant floor, fresh interior paint, fenced yard; etc. 2 car garage with 2 separate doors and remotes; Upgraded kitchen with stainless steels appliances, etc. Energy saving features include: CFL Lighting and Fixtures, Dual-Flush Toilets, ENERGY STAR Appliances,

Eileen Li TOPSKY REALTY INC

Stunning newer LAKEFRONT construction in the heart of Downtown Windermere completed in July 2024. This exquisite single-story home spans 2,868 sq ft with an open-concept design, featuring white oak hardwood floors and contemporary style throughout. Highlights include 4 bedrooms, each with its own en-suite bathroom, living room with expansive lake views, European-style kitchen, home office, and

Simon Simaan THE SIMON SIMAAN GROUP

This beautiful 4-bedroom, 3-bathroom home sits on a full 1-acre lot, surrounded by mature trees that provide exceptional privacy and a peaceful setting. The spacious, light-filled layout is perfect for both relaxed family living and entertaining.The primary suite includes his-and-hers walk-in closets, combining function and comfort with a touch of luxury. The home is also equipped with a

peipei Qiao BAY STREET GROUP FLORIDA LLC

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

One or more photo(s) has been virtually staged. Rent price includes Lawn service & Pool maintenance. This custom built home on over 1/2 acre looks out past an amazing stone water fall pool & gas fire pit to the beautiful sunsets of Central Florida. The fully updated 4 bedrooms, 3 baths, open floor plan executive home has it all from wood floors and Plantation Shutters throughout, to a Chef’s

Fred Flynn MILLENNIUM REALTY CENTER LLC

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

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. The downstairs features a private master suite with a guest suite with its own bath large garden tub, and an office or flex space perfect for

Courtney James LA ROSA REALTY ORLANDO LLC

One or more photo(s) has been virtually staged. Available Now! Luxurious + Spacious POOL home with 3-car garage located in the 24 hour GUARD GATED community of Reserve at Belmere in Windermere. Situated on a premium corner lot with a big yard and screened in pool area that is perfect for entertaining and all kinds of outdoor activities. Meticulously landscaped - both lawn and pool maintenance are

Brian Lemay ROMAN REALTY GROUP, LLC

Awaken to stunning sunrises in this exceptional Key West-style home, set on nearly an acre of prime lakefront property with 130 feet of direct access to the reknown Lake Butler— the crown jewel of the Chain of Lakes! Enjoy a vibrant lakefront lifestyle in a sought-after community featuring 13 interconnected lakes ideal for swimming, fishing, boating, and thrilling water sports.As you

Norma Lipscomb COLDWELL BANKER RESIDENTIAL RE

Stunning 3 bedroom, 2 bath pool home in the heart of Windermere is available for lease. This beauty features an open and modern floor plan. Beautifully appointed kitchen boasts sleek marble counter tops, a huge kitchen island and high end appliances. Wood floors thought-out home. Living area includes a wood-burning fireplace, large wall to wall sliding glass doors over looking a screened in salt

Cristina Porretto THE AGENCY ORLANDO

This recently remodeled HOME has 3-bedroom, 2-bathroom with spacious open living area, perfect for entertaining and everyday comfort. Inside, you'll find elegant ceramic tile flooring, adding a sleek and modern touch throughout the home. The kitchen is equipped with granite countertops and stainless-steel appliances. The primary bedroom offers a private retreat with a well-appointed bathroom,

Johany Utrera AVID REALTY LLC

Stunning Partially Furnished Rental in the Prestigious Keene’s Pointe Community of Windermere! This beautifully renovated home offers a modern, neutral palette with high-end finishes throughout. Step inside to a grand foyer leading to the formal dining room, where coffered ceilings and tall windows flood the space with natural light. The open-concept kitchen and living area is a chef’s dream,

Evan Caulfield STOCKWORTH REALTY GROUP

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

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

Luxury Home for Rent in Exclusive Windermere, FL !!! Don’t miss this incredible opportunity to live in one of Windermere’s most prestigious gated communities! This stunning 5-bedroom, 7-bathroom estate features elegant formal living and dining areas, a private home office, two spacious family rooms, and a game room with a built-in bar. Enjoy private access to Windermere Preparatory School,

Carola Garcia De Montenegro AGENT TRUST REALTY CORPORATION

Looking for a luxurious home in a prime location? Look no further! Located in the Isleworth Country Club, this Stunning single-family home at 6131 Payne Stewart Dr. is now available for rent. Situated in a fantastic waterfront location on Lake Chase, which is part of the Butler Chain of Lakes, this home is a short walk away from the world-renowned Isleworth Golf and Country Club. With

Jill Irwin IRWIN REALTY GROUP LLC

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