Kissimmee Vacation Homes for Sale

Search Kissimmee Real Estate Listings

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
Refine your search to less than 500 properties to save.
Click on the map to draw your polygon search.
Click on the map to draw your radius search.
Search only mappable listings within the map's bounds.
$13,000,000
 

4250 Boggy Creek Rd, Kissimmee

3 Beds, 2 Baths, 1,538 SqFt
Developers and Builders set your sights on this PRIME piece of Real Estate, few of which are left in Osceola County! This beautiful 80+ acres boasts with over 1600 feet of Lake Tohopekaliga access and over 200 feet of Boggy Creek frontage. Rectangular in shape, this piece of land is PERFECT for building that new luxury community that Boggy Creek is missing! Minutes from Lake Nona and Medical City, the Orlando International Airport, and walking
New
$1,650,000
 

2713 Formosa Blvd, Kissimmee

9 Beds, 11 Baths, 8,198 SqFt
Enter the private gates of Formosa Gardens Estates to see this magnificent Mediterranean style water front home. This exceptional 8,100+ square foot estate is custom built and is one of a kind in Formosa. It has been and is currently being used as an investment vacation rental because of its proximity to Disney World less than 2 miles as a crow flies from Animal Kingdom. This is a turn-key investment being sold exquisitely furnished and fully
$1,650,000
 

9054 Paolos Place, Kissimmee

5 Beds, 7 Baths, 6,312 SqFt
Luxurious lakefront living, within the shadows of Walt Disney World®, securely positioned behind its own private gates within a picturesque neighborhood. Welcome to Paolos Place: a heavenly oasis close to the magic but peaceful enough to be its own destination. This elegant mansion was the neighborhood builders' personal residence and packed with upgrades: smart home technology, soaring ceilings, custom millwork, tray ceilings, and an expansive
$1,427,300
 

985 Jack Nicklaus Ct, Kissimmee

5 Beds, 6 Baths, 4,485 SqFt
Under Construction. Under Construction. The Bear’s Den at Reunion has access to 3 golf courses, a tennis complex, water park, restaurants and community events. The impressive Clubhouse at Bear’s Den features a club restaurant, patio seating, fully stocked pro shop, men’s and women’s locker rooms, and a well-equipped exercise room. Owners, guests and renters at The Bear’s Den Club will have access to Reunion’s 5-star dining, 3 championship golf
$1,199,000
 

2617 Yountville Ave, Kissimmee

15 Beds, 15 Baths, 6,255 SqFt
Let the party begin located at the sought after guard gated community at Sonoma Resort built by Park Square Homes! This massive 6,255 SqFt (581 m2) resort home features 15 bedrooms, 15 baths (all keypad locked) and converted garage into a game room and in-house movie theater. A home fit for any family, you will find not 1, but 3 first floor Master Suites each with its own Master Bath. Further enhancing the space on first floor, 2 guest bedrooms
$1,149,000
 

3971 Oakville Ave, Kissimmee

10 Beds, 11 Baths, 6,404 SqFt
Welcome to a contemporary lover's dream home. This fully remodeled and fully furnished house could be your next home or an income property for years to come. It comes with all the furniture shown and everything needed for next day move-in. This massive 6,400+ home is conveniently located near major theme parks, highways and shopping plazas. The community is located next to the Shingle Creek Regional Park, which provides a charming backdrop of
$985,000
 

404 S Vernon Ave, Kissimmee

3 Beds, 2 Baths, 2,442 SqFt
Beautiful 1.66 acre site in walking distance to restaurants, entertainment, the courthouse and all that historic downtown Kissimmee has to offer. The lot, which includes a 2,442 sq. ft. original wood frame house built in 1894, sits directly across the street from Big Toho Marina with 238' fronting Lakeshore Blvd. The highest and best use of the property would likely be consistent with the City of Kissimmee's future land use designation of
$975,000
 

N/A, Kissimmee

5 Beds, 7 Baths, 4,966 SqFt
Colonial style two story on just over ½ an acre of land with your own personal pond and a view of woods. Covered front patio offers French door access into the home you’ve dreamed of your entire life. Wood flooring, soaring ceilings, decorative ceilings, and so much more! Office space is currently being used as a game room but would be great as a play area, craft room or anything else that may come to mind. The entry leads to the elegant wooden
$969,000
 

251 Falls Dr, Kissimmee

11 Beds, 13 Baths, 5,436 SqFt
Come see this 11 bedroom villa located at the Encore Club, less than 10 minutes to Disney World. Downstairs you have 4 bedrooms with en suites, including your Master Bedroom. Also on the bottom floor you have your laundry room and a powder room. On the second floor you have 7 more bedrooms, 5 with En Suites, an additional Family Bathroom and a powder room. For your entertainment, the upper floor loft area is equipped with a pool table and a
$950,000
 

2612 Yountville Ave, Kissimmee

14 Beds, 11 Baths, 6,255 SqFt
Back to the market .The loan fell through. the sought after guard gated community at Sonoma Resort built by Park Square Homes! This massive resort home features 14 bed rooms.A home fit for any family, you will find not 1, but 2 first floor Master Suites each with its own Master Bath. Designed with multiple families in mind, The house is guaranteed to be the solution to finding the vacation home of your dreams! The spacious island kitchen and
$925,000
 

7721 Banyon Way, Kissimmee

11 Beds, 13 Baths, 5,496 SqFt
This amazing 11 bed Biltmore home is located in the Encore club with its spectacular water park, plunge slides, restaurant, bar and other fantastic amenities, including child care, just 6 miles from Disney making it the perfect family home or rental vacation property. Its uniquely positioned as it has a huge pool, spa & sunny deck over looking green area and lake at the rear, giving a magnificent outlook. This home has an open plan concept
$914,900
 

7715 Banyon Way, Kissimmee

11 Beds, 13 Baths, 5,496 SqFt
Amazing Home Site and Location within Orlando's Premier Resort Community on this 11 bedroom elegant Villa located less than a 6 mile drive to Walt Disney World and their four amazing theme parks! This home is professionally decorated with a turn key vacation rental package, including themed rooms, and garage game room, sold Fully Furnished! The Encore Resort also offers exclusive on property amenities such as their thrilling water park with

KISSIMMEE 

Kissimmee has a relatively small historic Downtown are, which is quaint and full of exciting restaurants and a beautiful lake front park. In fact Kissimmee covers a very large area and houses around 69,000 residents, that number is dramatically increased every year by the millions of people from all around the world who come to visit Kissimmee, where a large portion of Vacation Homes and Villas are located to support the Orlando Vacation Market.

Historic Downtown KissimmeeKissimmee also includes townships such as Celebration, as master planned community and luxury Golf Resorts, Country Clubs and Vacation Home Communities such as Reunion Resort and Champions Gate. These are Close to Disney Orlando, withing 15 minutes drive and perfect locations to spend your leisure time while not working or enjoying the theme parks.

The list of activities to enjoy in Kissimmee is endless, take an air boat ride and enjoy viewing Alligators in their natural habitat or paddle around the "jungle" in a Kayak. Try your hand at Crazy Golf or even the real thing at the many world class golf facilities that Kissimmee has to offer. There are just simply too many restaurants to ever visit them all and a good selection of Dinner Shows.

Old Town, is unique, wander around and see a slice of Americana in action or visit the neighboring Fun Spot where you can dare yourself to take the Sky Ride or keep your feet on the ground and pick up those Florida Disney Souvenirs that you need to bring back to your home to help you remember this in this funky and fun town.

Owning a property here could be a good decision, either a vacation home, villa or condo in Kissimmee with it's close proximity to Disney Orlando makes it almost an unbeatable choice. There are also many opportunities to live the dream here in Kissimmee  where employment is generally better than the national average due to the demands of the service industry and tech companies.  Kissimmee is of course well located to support Lake Nona and it's rapid growth in Health and Science related jobs at places such as Nemours.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on July 23rd, 2019 at 8:15am EDT.