Kissimmee Short Sales - 45 homes

Remarks: Short Sale. LOWEST PRICED 7 BEDROOM! Turnkey 7-Bedroom Vacation Home in Windsor at Westside – Active Short-Term Rental! Welcome to 1861 Nice Court, a beautifully furnished and actively producing 7-bedroom, 5-bathroom short-term rental located in the sought-after Windsor at Westside Resort. With 3,281 sq ft of living space, this stunning home is designed to impress guests and maximize occupancy—making it the perfect investment property or vacation retreat near the magic of Disney. Step inside to a bright, open-concept layout featuring a spacious living area, modern kitchen with stainless steel appliances, and generous dining space ideal for large families and groups. This home offers multiple ensuite bedrooms and themed guest rooms that delight visitors of all ages and keep bookings strong year-round. The private screened-in pool and patio provide the perfect place to unwind after a day at the parks, offering your guests the relaxation and resort-style experience they’re searching for. Located in the gated, 24-hour resort community of Windsor at Westside, owners and guests enjoy unmatched amenities including an 8,000+ sq ft clubhouse, fitness center, resort-style pool, waterslide, lazy river, volleyball court, tennis courts, and a full activity-filled play zone. The HOA covers lawn maintenance, internet, cable, daily valet trash service, and access to all resort amenities—making ownership truly hassle-free. Just minutes from Walt Disney World, Margaritaville, Sunset Walk, shopping, dining, and major attractions, this property offers strong rental history, excellent future booking potential, and a turnkey setup ready for its next owner. Whether you're looking to expand your STR portfolio or secure a high-performing vacation home, 1861 Nice Court is an exceptional opportunity in one of Central Florida’s premier resort communities.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Michael Steward (386-243-9585)

Remarks: Short Sale. This is a short sale! Sold as is! Third party approval required!

Listing is courtesy of: TOP SAVING REALTY (407-846-0573)

Listing Agent: Sonya Dietsch (407-666-4515)

Remarks: Under contract-accepting backup offers. Short Sale. Welcome to your dream vacation home! This stunning property located in Paradise Palms is a great short term rental opportunity and offers 4 bedrooms and 3 bathrooms, perfect for creating lasting memories with friends and family or renting it out for a little extra income. The open kitchen and spacious layout provide exactly what vacation guests are looking for when booking their Orlando vacation. Step outside to a private dipping pool that promises fun and relaxation under the Florida sun. Enjoy the peaceful pond view while sitting on the patio, perfect for unwinding after a day of adventure at the parks. This home is beautifully updated with granite counters in the kitchen and a large bar area, making it an ideal space for entertaining. Paradise Palms features resort-style amenities, including a lagoon pool complete with slides and waterfalls, an arcade, and a theater room. The community is guard-gated and beautifully landscaped, offering the perfect backdrop for your enjoyment. This property is not only a great vacation spot but also a great short-term rental opportunity that is booked regularly. With its prime location within 20 minutes of Disney, you have access to some of the best attractions Florida has to offer, while still having some peace and quiet away. Enjoy the vibrant, happy vibe of this home while earning extra income during the off-season.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Anne-Marie Wurzel (407-702-3610)

Remarks: Under contract-accepting backup offers. Short Sale. Stylish 3BR/2.5BA Townhome with 2-Car Garage! Step into a bright, open floor plan with a sleek modern kitchen with granite counter tops, stainless steel appliances, and plenty of storage. Retreat to the spacious primary suite with walk-in closet and dual-sink bath. Flex space on second floor for office or play area. Enjoy your private patio with no back neighbors, 2-car garage, and resort style community amenities such as pools, tenis court, playground—all minutes from shopping, dining, and major highways. Move-in ready!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Chisselle Sanchez (407-230-5433)

Remarks: Under contract-accepting backup offers. Short Sale. Short Sale – Home with Great Potential! Welcome to this 5-bedroom, 3.5-bath custom home on 2.38 private acres at the end of a secluded dead-end street. This property offers the perfect mix of space, privacy, and opportunity. Enjoy outdoor living with a pool, covered porch, and outdoor kitchen—ideal for entertaining. A 4-car garage with attached workshop and plenty of space for RVs, boats, and trailers makes this home perfect for hobbyists and adventurers alike. Inside, you’ll find a spacious kitchen with matte granite countertops, Wolf appliances, Sub-Zero fridge, and travertine flooring. Custom touches include tongue-and-groove Aspen ceilings, Pecky Cypress wood accents, and cedar-lined closets. The space above the garage, was used as a gym, offers flexibility, convert it into a rental, guest suite, or office. While the well is not currently working, this property is filled with potential to be transformed into your dream retreat.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III REALTY (407-207-0825)

Listing Agent: Jessica Estrada (863-409-1771)