kissimmee vacation homesKissimmee, FL Vacation Homes

What do the popular theme parks Walt Disney World, Universal Orlando and Sea World have in common? They’re located right next door to Kissimmee, Florida. The city is located just outside Orlando in Osceola County, and is one of the fastest growing communities in Florida.

Kissimmee is a family-friendly community that is not only a great place to visit, but a better place to call home. Many people who visit from cold weather states like Michigan and New York, as well as frequent travelers from Canada and Europe, find Kissimmee so appealing that they buy second homes here. It’s no wonder because Kissimmee vacation homes offer great access to a thriving downtown district and a high level of municipal services.

Check out the available Kissimmee vacation real estate below, or continue reading to learn more about the many wonderful holiday communities found in the city!

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
402 Properties Found. Showing Page 1 of 34
View As: Map
Sort by:

4445 Austin Road, KISSIMMEE

New Photo of Listing #O5979928

$2,500,000

  • 3 Beds
  • 2 Baths

  • 2,624 SqFt
  • 8.02 Acres

Single Family Residence

Acreage & Unrec

Possibilities Are Endless. This Is A Remarkable Opportunity For An Investor/builder Looking To Develop A Small New Subdivision Of Single-family Homes, Townhomes, Duplexes, Etc., Or This Is Your Chance To Own A Small Paradise For Your Own Private Residence. This Is A Beautiful, Tucked Away From Traffic Lot, A Little Over 8 Acres. The Property Currently Includes A 3 Bedroom, 2 Bath Home, A Separate Single Wide Mobile Home, A Horse Paddock, Fenced In Horse Field And A Barn/workshop. At This Time, Property Is Zoned As Agricultural Which Can Be E...

3102 Parrot Head Place, KISSIMMEE

New Photo of Listing #O5988368

$2,499,500

  • 8 Beds
  • 9 Baths

  • 4,815 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 5

Uniquely Rare Opportunity To Own The Largest 8 Bedroom, 9 Bathroom Vacation Home Floorplan Here In Margaritaville Resort Orlando! This 4689 Sq Ft Model Is Conveniently Located Steps Away From Disney World's Back Gate. Resort Amenities To Include Pool, Fitness Club, Spa, Hotel And Only A Short Walk To The Shopping And Dining Of Sunset Walk. Margaritaville Is Only A Half Hour From Orlando International Airport.

2960 Frontier Drive, KISSIMMEE

New Photo of Listing #O5966089

$2,400,000

  • 5 Beds
  • 4 Baths
  • 1 Half

  • 5,464 SqFt
  • 10.10 Acres

Single Family Residence

Pine Oaks

Unique 10.1 Acre Estate In The Perfect Location For Privacy, Convenience And Fun! Beautiful Country Setting With Private Access To East Lake Tohopekaliga. Property Features The Main House, A Guest House, Storage/animal Shed And A Workshop. The Main House Of 4,187 Sq. Ft. Features 3 Bedrooms, 3.5 Baths, A Large Family Room With A Gas Fireplace And Pool Table, Large Kitchen With Plenty Of Cabinetry And Counter Space, Upgraded Stainless Steel Appliances And Beautiful Stone Accents. This Home Has A Very Large Screened-in Pool With An Island, Ove...

4421 Reaves Road, KISSIMMEE

New Photo of Listing #S5031594

$2,200,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 5,044 SqFt
  • 41.01 Acres

Single Family Residence

Bobbie Jean Acres

This Stunning, Custom Designed And Custom Built Home Is A Once In A Lifetime Opportunity. Imagine Yourself Driving In Through The Private Gated Entrance, Past The Serene Pond, And Up To The Perfectly Landscaped Front Yard. This Home Has All The Little Details You Could Ask For: Crown Molding, Additional Recessed Lighting, Built Ins, Study Nooks, And Many Architectural Touches Throughout. Walk Into The Formal Living Room With Windows That Let The Florida Sunlight Stream In. The Spacious, Open Kitchen Boasts Both A Bar With Seating And An Isla...

1503 Sunset Pointe Place, KISSIMMEE

New Photo of Listing #O5997399

$2,150,000

  • 5 Beds
  • 4 Baths

  • 4,063 SqFt
  • 0.66 Acres

Single Family Residence

Sunset Pointe

This Elegant Florida Style Home With Breathtaking Sunsets Illuminating The Sky This 5 Bed, 4 Bath Plus Bonus Room And Office With Over 4,000 Sqft Of Living Space. The Gathering Room Is Equipped With A Surround Sound Home Theater, Custom Cabinets, Gas Fireplace, 20+foot Ceilings With Custo Mill Work And Architecturally Pleasing Features. The Spacious Gourmet Kitchen With Lavish Custom Cabinets And Morning Room Is Ideal Location For Cooling Up A Sensational Feast Of Fun. Office Room With Custom Cabinetry Is Elegant Appointed. Gated Community...

3056 Parrot Head Place, KISSIMMEE

New Photo of Listing #O5988786

$1,950,000

  • 8 Beds
  • 8 Baths
  • 1 Half

  • 4,131 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 5

Spectacular Waterfront Cottage On Margaritaville Resort Orlando's 'trophy Row'! Fantastic Opportunity To Own One Of The Largest Waterfront Cottages With Pool And Spa Plus Your Very Own Elevator ($40k Upgrade)! Home Is Fully Handicap Accessible. Huge 4131-a Model, 8 Bedrooms, 8 Full Bathrooms And 1 Half Bathroom With In Paradise Upgrade Package. This Amazing Home Features Two En Suite Bedrooms On First Floor, Large Kitchen With Tiled Backsplash And Breakfast Bar, Spacious Pantry With Custom Shelving, Living Room With Sliders That Lead To Beau...

212 South Clyde Avenue, KISSIMMEE

New Photo of Listing #O5992515

$1,500,000

  • 4 Beds
  • 3 Baths

  • 4,292 SqFt
  • 0.56 Acres

Single Family Residence

Patricks Add

Beautiful 4 Bedroom 3 Bath Historic Pool Home W/ An Impressive Wrapping Porch In Downtown Kissimmee On An Oversized Lot With A Huge Victorian Style Balcony W/ A Huge 3 Car 30x30 Detached Garage/ Workshop Offering Plenty Of Storage, Compete W/ A Carriage House Converted To A Detached Office Or Gym. Plenty Of Space To Park On The Circle Drive In The Front Of The Home Or The Extended Drive That Wraps Around To The Rear Of Home. Relax In The Impressive 38 Foot Pool With Plenty Of Space To Entertain On The Oversized Pool Deck & Outdoor Gas Grill....

8525 Patricia Trail, KISSIMMEE

New Photo of Listing #O5991147

$1,440,000

  • 6 Beds
  • 5 Baths
  • 1 Half

  • 5,157 SqFt
  • 5.01 Acres

Single Family Residence

Happy Trails Unit 03 Unrec

This Turnkey Magnificent Home Sits On Over 5 Acres Of Peaceful, Serene, Natural Beauty. Custom Built In 2017 This House Boasts Three Master Suits With Walk In Closets, Soak In Bathtubs Standalone Showers And Duel Sinks, It Also Has An Open Loft Area, High Ceilings, Large Windows, Sliding Glass Doors Opening Out From The Family Room And Downstairs Master Bedroom To The Huge Screened Pool And Spa In This Courtyard Style Setting. The Open Plan Kitchen Has Solid Wood Cabinets, Granite Countertops, Large Pantry, State Of The Art Appliances With...

249 Auburn Avenue, KISSIMMEE

New Photo of Listing #O5997099

$1,400,000

  • 12 Beds
  • 12 Baths
  • 1 Half

  • 6,351 SqFt
  • 0.24 Acres

Single Family Residence

Reunion West Ph 4

Do Not Miss Your Chance To Own This Highly Successful Vacation Rental With Rave Reviews And With An Opportunity For $120,000 Of Current Future Bookings To Convey To The Next Owner. Bookings Subject To Change. This Stunning 12 Bedroom 12 1/2 Bath Private Pool Home Located On The West Side Of Encore Resort At Reunion And Is Short Walk To All Of The Amazing Amenities. The Home Offers An Open Floor Plan With A Coastal Design With Plenty Of Space For You To Entertain Family & Friends. The Spacious Chef's Kitchen Is Equipped With Stainless Applian...

7704 Westland Drive, KISSIMMEE

New Photo of Listing #O5974427

$1,300,000

  • 10 Beds
  • 9 Baths

  • 5,138 SqFt
  • 0.17 Acres

Single Family Residence

Reunion West Ph 4

This 10 Bedroom Is Located At The Encore Club, Less Than A 10 Minute Drive To Walt Disney World And Their Four Amazing Theme Parks! The Private Patio With A Swimming Pool And Spillover Spa Is The Perfect Way To Enjoy Florida's Sunshine And The Home Theater Is The Only Way To Relax After Long Days At The Theme Parks Where You And Your Loved Ones Can Watch Your Favorite Movies Together! Main Living Area: Spacious Comfortable Seating Area With 3x Sofas Overlooking The Private Pool Deck Through Sliding Glass Doors Kitchen: Fully Equipped W...

1662 Marina Lake Drive, KISSIMMEE

New Photo of Listing #O5978243

$1,199,000

  • 5 Beds
  • 4 Baths
  • 2 Half

  • 5,409 SqFt
  • 0.58 Acres

Single Family Residence

Ashley Cove Unit 02

This Impeccably Kept Five-bedroom, Five-bath Home Is Perfect For A Large Family Or Even Multiple Families With The Potential For A Sixth Bedroom. The Spacious, Uniquely Designed Master Suite Includes A Sitting Area To Read Your Favorite Book As Well As Four Closet Areas To Keep All Your Belongings Organized. The Family-style Kitchen Opens Into The Spacious Living/media Area That Features Beautiful Custom Wood Cabinetry. As You Climb The Stairs Or For Those That Have The Necessity, Use The Acorn Stairlift, You Find An Oversized Bonus Room To ...

7657 Wilmington Loop, KISSIMMEE

New Photo of Listing #S5048774

$1,095,000

  • 10 Beds
  • 10 Baths

  • 4,723 SqFt
  • 0.18 Acres

Single Family Residence

Reunion West Ph 1 West

Back On The Market! A High Performing, Exceptionally Maintained, 10 Bed 10 Bath Home On An Over-sized South East Facing Rear Lot Within A Short Walking Distance To The Clubhouse And Amenities And Easy Access To The Back Gate. Located In The Spectacular Encore Club Resort, A Family Fun Filled Vacation Community Designed To Exceed Your Expectations With Features For All Ages, Such As A Huge Water Park, Exhilarating Water Slides, Drop/splash Tower, Enormous Pool, Tennis Courts, Basketball Court, Beach Volleyball, Fitness Club, Restaurants, Full...

kissimmee real estateThe Kissimmee Community

The city’s unusual name is said to be the modern spelling of a tribal word from one of Florida’s lesser-known tribes, the Jororo. A 1752 Spanish map used the name “Cacema,” which has evolved into today’s spelling of Kissimmee.

In the early to mid-20th century, Kissimmee’s economy was based on cattle, citrus and other crops. Retirees were encouraged to move here in the 1950’s. Kissimmee real estate really took off after Walt Disney World was built in the 1970’s. Since then, other theme parks and attractions followed, such as Fun Spot America, Gatorland, Kissimmee Air Museum, as well as several dinner theaters and miniature golf parks.

Kissimmee Real Estate Market

Kissimmee vacation home buyers also choose the city because of the wide range of parks and recreational activities that are available, including Lake Tohopekaliga, which offers some of the best bass fishing in the world.

Nature lovers can enjoy a thrilling airboat ride and discover a world alive with tropical birds, turtles and alligators. There are plenty of championship golf courses nearby that are ideal for the beginner or professional golfer. And you’ll find a mix of dining options and unique shopping venues in the area too.

One reason people buy Kissimmee vacation real estate as a second home is to generate income by renting out the property to visitors. If you’d like more information about the homes for sale in Kissimmee that can be rented as a vacation property, please contact a Team Donovan agent online today or call 407-705-2616.

^ Back to: Kissimmee Real Estate

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 January 19th, 2022 at 11:23pm EST.