Kissimmee Vacation Homes for Sale

Elegant 4-Bedroom, 3-Bathroom Luxury Residence on Premium Lot at Celebration. Welcome to this beautifully maintained 4-bedroom, 3-bathroom home nestled in the sought-after community of Celebration, Florida! This spacious residence offers a perfect blend of comfort, functionality, and style—ideal for families, professionals, or anyone looking to enjoy the unique lifestyle Celebration has.

Under contract-accepting backup offers. Discover an extraordinary vacation home that blends luxury living with resort-style ambiance. This 11-bedroom, 10.5-bathroom estate sits in Encore at Reunion, a coveted community in the Orlando area, offering a premier lifestyle just moments from world-class attractions.

LAKEFRONT LUXURY LIVING in Bellalago! No rear neighbors, Just lake views! Welcome to this expansive Mediterranean-inspired estate set directly on Lake Tohopekaliga. Built in 2019, this stunning 5,412 sq ft home combines timeless architecture with modern function—offering two 2-car garages, including one oversized with a built-in workshop—perfect for car enthusiasts or hobbyists.

Welcome to this perfect investment home at Veranda Palms. These 12 bedrooms, 11.5 baths offer all the comfort and design to maximize the resort living experience. Has two master suits, one on each floor.This fully furnished home with spacious rooms, elegant décor, and a gourmet kitchen, has a modern and open layout making it very bright and easy to entertain.

FULLY FURNISHED 8 Bed/ 5 Bath WATERFRONT VACATION HOME IN STOREY LAKE RESORT! Turnkey investment property with high rental income potential. Professionally decorated and designed for comfort and style. Open floor plan, spacious living area, themed bedrooms (princess, toy story, avengers, the Lion king) and game room (Star Wars).

7616 Brookhurst Lane in the Encore Resort at Reunion, Kissimmee, is a standout opportunity for short-term rental investors or families looking for a luxury vacation retreat just minutes from Orlando’s top attractions.

Welcome to Lakeside Adventure Villa, an exceptional short-term rental investment opportunity in one of Orlando’s most sought-after vacation destinations. This 10-bedroom, 8-bathroom home with a 2-car garage is fully furnished and ready to generate income from day one. The spacious floor plan accommodates up to 23 guests, making it ideal for large families, reunions, or group getaways.

Discover this six-unit apartment building nestled in the heart of historic Kissimmee, originally built in 1920. This maintained property offers a rare chance to own a piece of downtown's vibrant landscape - an unbeatable location within walking distance to the Osceola Courthouse, premier dining, shopping, Lake Tohopekaliga & a only a short drive to Disney.

Welcome to your next home in the prestigious gated community of Kissimmee Bay Country Club! This spectacular, fully renovated residence blends luxury, advanced technology, and comfort, all set in a breathtaking natural environment overlooking the majestic Lake Toho. The home offers 5 spacious bedrooms and 4.5 bathrooms.

Welcome to 4261 Twilight Trail, a stunning custom-built estate nestled on 5 private acres in the heart of Kissimmee. This property was thoughtfully designed with comfort, quality, and style in mind, featuring numerous upgrades throughout the home. Enjoy the perfect balance of space and privacy while still being close to shopping, dining, schools, and major highways.

Welcome to Regal Cove – Modern Luxury Meets Country Charm! Imagine living in the exclusive, gated community of Regal Cove, where this fully renovated custom home offers both elegance and privacy. Set on nearly half an acre (.49), this residence boasts one of the largest private screened lap pools in the area with a heated spa—perfect for entertaining or relaxing year-round.

Check out these Numbers!!! 2022 April-Dec: $203026 2023 Yr: $246271 2024 Yr: $181007 9 Bedroom! Storey Lake! Star Wars-Themed Game Room! Get ready to experience the ultimate vacation home and investment property in the popular Storey Lake Resort in Kissimmee! *Fully furnished home. *Two bedrooms located on the main floor—perfect for guests of all ages.