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!

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1,195 Properties Found. Showing Page 1 of 100
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1051 Jack Nicklaus Ct, Kissimmee

Photo of Listing #O5711133

$1,728,900

  • 7 Beds
  • 7 Baths
  • 1 Half

  • 5,410 SqFt
  • 0.18 Acres

Single Family / Villa

Reunion West Fairways 17...

Under Construction. Luxurious Custom Home Behind The Gates Of Bear’s Den At Reunion. World Class Destination 10 Minutes From Walt Disney World With Access To 3 Golf Courses, A Tennis Complex, Water Park, Restaurants And Community Events. The Impressive Clubhouse At Bear’s Den Now Under Construction Will Feature A Club Restaurant, Patio Seating, Fully Stocked Pro Shop, Men’s And Women’s Locker Rooms, And A Well-equipped Exercise Room. Custom Home Built By Encore Offers Exceptional Detail And Outstanding Craftsmanship. This Transitional Home ...

1081 Jack Nicklaus Ct, Kissimmee

Photo of Listing #O5711154

$1,647,530

  • 8 Beds
  • 8 Baths
  • 2 Half

  • 5,785 SqFt
  • 0.24 Acres

Single Family / Villa

Reunion West Fairways 17...

Under Construction. Luxurious Custom Home Behind The Gates Of Bear’s Den At Reunion. World Class Destination Only 10 Minutes From Walt Disney World. Luxury Custom Home Built By Encore Offers Exceptional Detail And Outstanding Craftsmanship. This Contemporary Home Will Have 8 Bedrooms With A Master Suite Downstairs, 8 Full Baths And 2 Half Baths, Gourmet Kitchen Featuring 2 Islands, Open Concept Kitchen/dining/family Room, And A Substantial Game Room Upstairs. The Expansive Covered Lanai Has A Fireplace, Summer Kitchen And A 22 X 30 Pool With...

2960 Frontier Dr, Kissimmee

Price
Reduced
Photo of Listing #O5727356

$1,500,000

  • 5 Beds
  • 4 Baths
  • 1 Half

  • 5,111 SqFt
  • 10.10 Acres

Single Family / Villa

Pine Oaks

Welcome Your Family/estate On 10 Acres. Wonderful Country Setting With Loads Of Privacy Located On East Lake Toho Which Is Part Of A Chain Of Lakes And Both Skiable And Able To Land A Sea Plane. Property Features The Main House, A Guest House, Mobile Home, Playhouse, Storage Shed, And A Huge Workshop. Large Circular Driveway With Loads Of Parking. The Main House Of 4187 Sq. Ft. Features 3 Bedrooms, 3 1/2 Baths, Large Gathering Room With A Gas Fireplace, Large Kitchen For The Chef In The Family, Cabinets Galore, Center Island. This Home Has A...

2365 Thacker Trl, Kissimmee

Photo of Listing #O5727045

$1,250,000

  • 7 Beds
  • 7 Baths
  • 1 Half

  • 7,829 SqFt
  • 5.54 Acres

Single Family / Villa

Happy Trails

Situated On 5.5 Prime Acres Boasts A Private Custom Built Mediterranean Estate Offering The Finest Luxurious Details Throughout. Stately Gates Open To A Circular Paved Driveway With A Center Piece Four Tier Fountain. In Impeccable Condition, This Property Makes An Ideal Home Or Retreat With Ample Accommodation For Guests Including 7 Bedrooms, 7.5 Bathrooms In Over 7,800 Square Feet Of Living Area. Ten Foot Solid Mahogany Arched Doors With A Sweeping Solid Oak Free Standing Staircase And Chandelier Greets You At The Elegant Foyer. The Large P...

3501 Harbor Rd, Kissimmee

Photo of Listing #S4856774

$1,200,000

  • 4 Beds
  • 3 Baths

  • 2,139 SqFt
  • 9.48 Acres

Single Family / Villa

Obar Ranchettes

Opportunity Of A Lifetime Is You Are Looking For Country Living On 9.48 Acres, Two Homes And Located Not Far From Town. The Main House Was Custom Built In 2016, 4 Bedrooms,3 Baths, Spacious Great Room, Open Kitchen, Wood Burning Fireplace, Split Bedroom Plan, Front And Back Screened Porches To Enjoy The Peace And Quiet Of Country Living. Barn With Electric And Water, Detached Workshop With Electric... Garage Is Double Insulated, Which Makes Great Game Room. The Second Home On This Property Is The Homestead Of The Original Owners.. 3 Bedroom...

404 S Vernon Ave, Kissimmee

Photo of Listing #O5715617

$1,200,000

  • 1 Beds
  • 2 Baths

  • 2,442 SqFt
  • 1.66 Acres

Single Family / Villa

Johnson Lillie Resub

1.66 Acre Site, Which Includes A 2,442 Square Foot Original Wood Framed Home Built In 1894. Directly Across The Street From Big Toho Marina With Approximately 238' Fronting Lakeshore Blvd. Walking Distance To Restaurants, Entertainment, The Courthouse, Etc.... The Home Could Be Renovated, However, The Highest And Best Use Of The Property Would Likely Be Consistent With The City Of Kissimmee's Future Land Use Designation Of Mixed-use Downtown (mu-d).

2617 Yountville Ave, Kissimmee

Photo of Listing #O5729884

$1,199,000

  • 15 Beds
  • 15 Baths

  • 6,255 SqFt
  • 0.33 Acres

Single Family / Villa

Sonoma Res/tapestry Ph 1

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 And 2 Guest Baths Will Be Ideal For Any Family Member Or Guest. Designed With Multiple Families In...

241 Falls Dr, Kissimmee

Price
Reduced
Photo of Listing #S4856880

$975,000

  • 11 Beds
  • 10 Baths
  • 3 Half

  • 5,436 SqFt
  • 0.21 Acres

Single Family / Villa

Reunion West Ph 2a West

The Most Beautiful And Well Located Home At Encore. This Pristine 11 Bedrooms, 10.3 Bathrooms Single Family Home Is Nested On The Perfect Lot That Provides A Stunning View And Easy Access To The Water Park. This Turnkey Home Features Many Great Leisure And Social Seating Areas And Includes A Fully Equipped And Well Decorated Home Theater. Its Kitchen Is Fully Equipped With A Beautiful Granite Countertop Breakfast Bar Style. Two Double Door Stainless Steel Refrigerator, Double Built In Ovens And 2 Dishwashers. There Is A Laundry Downstairs ...

3620 Reaves Rd, Kissimmee

Photo of Listing #S4825314

$900,000

  • 4 Beds
  • 3 Baths

  • 3,296 SqFt
  • 2.01 Acres

Single Family / Villa

Acreage & Unrec

Great Location In Growing Area And With 4 Bedrooms And 3 Baths It's Ready For Your Family To Move In And The Florida Lifestyle. Near Shopping, Restaurants, And Schools.

491 Burma St, Kissimmee

Price
Reduced
Photo of Listing #O5704104

$899,000

  • 11 Beds
  • 10 Baths
  • 3 Half

  • 5,436 SqFt
  • 0.21 Acres

Single Family / Villa

The Encore Club

This Is The Home You Have Been Waiting For, No Need To Wait To Build Or Get Set Up In A Rental Program. This Home Is Turnkey In A Fully Marketed And Managed Jeeves Management Program. Professionally Decorated This Vacation Home Is In Mint Condition And Is Sold Fully Furnished And Rental Ready. All Stainless Steel Appliances, Luxury Bedroom Suits, Two Large Sitting / Media Areas, Large Flat Screen Samsung Hd Televisions In All Rooms, A Beautifully Equipped Games Room And Private Cinema Make This Home The Ideal Luxury Vacation Rental Property....

7697 Fairfax Dr, Kissimmee

Photo of Listing #T3121057

$890,000

  • 11 Beds
  • 7 Baths
  • 3 Half

  • 5,436 SqFt
  • 0.29 Acres

Single Family / Villa

Reunion West Ph 3 West

Located In The Beautiful Encore Resort, This Gorgeous Home Is Turn Key, Professionally Decorated And Being Sold Fully Furnished. Property Features A Heated Pool And Hot Tub, Stainless Steel Appliances, Built In Double Oven, Large Flat Screen Televisions In Every Room, A Private Home Theater, And Theme Rooms That The Entire Family Is Sure To Fall In Love With! This Home Is Loaded With Amenities And Entertainment Options That Make It The Ideal Luxury Vacation Home. This 11 Bedroom "biltmore" Model Is Designed With Luxury And Comfort In Mind. D...

2595 Michigan Ave, Kissimmee

Price
Reduced
Photo of Listing #S4858526

$875,000

  • 3 Beds
  • 2 Baths

  • 1,656 SqFt
  • 4.72 Acres

Single Family / Villa

Acreage & Unrec

Price Reduction...investors......incredible Opportunity! This Prime Property Has App. 5 Acres With App. 220 Ft Frontage On Michigan Ave Near Kissimmee Post Office. A Must See!! Easy Access To Shopping Mall, Fl Turnpike And Osceola Pkwy And Orlando International Airport. Seller Is Very Motivated And May Be Willing To Do Seller Financing. Call Us For More Information.

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.

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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.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on September 18th, 2018 at 11:30am EDT.