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Vacation Homes for Sale in Kissimmee, FL

473 homes
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343 Indian Wells Ave, Kissimmee, FL 34759

YOUR FLORIDA OASIS AWAITS! This stunning, fully-updated WATER VIEW home is ready for its next loving owner! As you enter, you are greeted with a spacious open-concept living space, with easy access t...
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9032 Flamingo Key Way, Kissimmee, FL 34747

This stunning and beautifully decorated 6 bedroom home with a stunning blend of tasteful decorated design for the adults and amazing theme rooms. The Grand Living allows for comfortable lounging and ...
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8531 Bay Lilly Loop, Kissimmee, FL 34747

Stunning Home in Encantada - Perfectly Located! Welcome to your dream home! This beautiful home in the exclusive Encantada resort offers everything you need for a relaxing and live your best life. Th...
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3838 Bowfin Trl, Kissimmee, FL 34746

^^Price Improvement^^ Live the Resort Lifestyle Every Day! This stunning Tuscany-inspired 6-bedroom, 4-bathroom, 4-car garage home, spanning 4,406sf home is nestled in the highly sought-after Bellala...
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3206 Holderness Dr, Kissimmee, FL 34741

This great 3 bedroom, 2.5 bath townhome in the gated community of FLORA RIDGE could be yours! The kitchen features brand-new, never-before-used appliances that open to a spacious dining and living ar...
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7443 Marker Ave, Kissimmee, FL 34747

Welcome to the exclusive Encore Club in the sought-after Reunion West Community. This property comes with transferable membership, management, and rental data all in one for ease. This 5-star resort...
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855 San Pedro Ct, Kissimmee, FL 34758

Welcome to your dream home located in the desirable Poinciana community of Kissimmee! This spacious 3-bedroom, 2-bathroom residence sits on a large almost quarter acre lot and boasts a PRIVATE POOL, ...
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8014 Knee Deep Rd, Kissimmee, FL 34747

ATTENTION SELLER MOTIVATED!!! This exited 4-bedroom, 4-full bath 2 Story Home must go. With a PRIVATE HEATED POOL & SPA IN the heart of MARGARITAVILLE MINUTES FROM DISNEY, WITH A HUGE FENCED BACKYARD...
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3156 Britannia Blvd Unit D, Kissimmee, FL 34747

$25,000 price drop! This tastefully-decorated, DISNEY-AREA condo can be used as a VACATION RENTAL, long-term rental, or primary residence. Located within a GATED COMMUNITY just off of Hwy 192, enjoy ...
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1027 Park Ridge Cir, Kissimmee, FL 34746

Welcome to the Vacation Townhome of your dreams! This gorgeous 3 bedroom 2.5 bath with 1,291 SqFt of living space is waiting for you, but not for long! Stepping inside you are greeted by the bright a...
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4939 WORCHESTER DRIVE, KISSIMMEE, FL 34746

BRAND NEW HOME!! Welcome to your new 4-bedroom, 2-bathroom home in the desirable Knightsbridge community. Ideal for growing families or those who love to entertain, this residence offers a generou...
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4256 Fort Courage Cir, Kissimmee, FL 34746

Discover this well-maintained 4-bedroom, 2-bathroom, 1888', gem with a spacious 2-car garage, nestled on a generous quarter-acre lot. The highlight of this home is the large pool, surrounded by a scr...
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1466 Londra Ln, Kissimmee, FL 34744

Welcome to your dream home in the heart of Kissimmee! Beautifully maintained 3-bedroom, 2-bathroom block ranch-style residence, a perfect blend of comfort, convenience, and privacy. With only one own...
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2132 Antilles Club Dr, Kissimmee, FL 34747

Discover upscale living in the sought-after 55+ community of Four Seasons at Orlando with this beautifully crafted 2-bedroom, 2-bathroom home, featuring a state-of-the-art water filtration system and...
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7564 SUNFLOWER CIRCLE, KISSIMMEE, FL 34747

Stunning 5-Bedroom Townhouse Near Disney – Perfect for Residential or Short-Term Rental! This practically new 5-bedroom, 5-bathroom townhouse is a rare gem, offering unparalleled convenience and luxu...
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1832 Sandy Park Trl, Kissimmee, FL 34747

This property listing describes a fully furnished, turn-key single-family vacation home in the highly sought-after Solara Resort near Disney. This home is an excellent income-producing short-term ren...
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1410 Celebration Ave Unit 407, Kissimmee, FL 34747

Welcome Home to Penthouse Living! This beautiful two bedroom/two bath condominium is located on the top floor with breathtaking views of the gorgeous Artisan Park Village in the exciting town Disney ...
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5000 Mangrove Aly Unit 202, Kissimmee, FL 34746

Absolutely gorgeous fully furnished 2nd floor waterfront condo with an open feel that’s perfect for your own personal getaway or income producing AirBNB near Disney and other attractions. You’ll love...