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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1,109 Properties Found. Showing Page 1 of 93
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9054 Paolos Pl, Kissimmee

Price
Reduced
Photo of Listing #O5551992

$1,650,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 6,312 SqFt
  • 1.64 Acres

Single Family / Villa

Westside Parcel D Calabria

This Is The Home Of Your Dreams! Enjoy The Private Luxuries Of Skiing, Boating & Living On Almost 2 Acres Of Private Land Nestled On Beautiful Lake Davenport. This Custom Architectural Estate Home Boasts Beautiful Landscaping, A Bright & Open Floor Plan, The Finest Architectural Details & Finishes, And Is A State-of-the-art Smart Home. Control Everything W/ A Touch Of A Finger! The Open Floor Plan Boasts A Formal Living Room, Family Room, & Formal Dining Area. Windows Abound Allowing The Natural Beauty Of The Outdoors To Be Enjoyed Throughou...

1388 Grandview Blvd, Kissimmee

Price
Reduced
Photo of Listing #O5558479

$1,350,000

  • 6 Beds
  • 5 Baths
  • 1 Half

  • 9,029 SqFt
  • 0.80 Acres

Single Family / Villa

Regal Point West

New Price! Sellers Says Make An Offer! Impressive Lakefront Estate With Pool, Overlooking A 22,000 Acre Lake, And Nestled In Gated Estate Community - Offered By Motivated Seller -all Furnishings Included If Desired By Buyer ! Don't Miss This ! 5-6 Bedrooms! 9000+ Sq.ft. Living Area! Over 400+' Of Direct Lake Frontage - Awesome Views And Unparalleled Quality Construction! Timeless Architecture – All Brick Construction (low Maintenance!) Built To Last – And Treasured For Years To Come ! A Grand Marble Foyer With Impressive Two-story Sta...

991 Jack Nicklaus Ct, Kissimmee

Photo of Listing #T2914514

$1,317,900

  • 6 Beds
  • 6 Baths
  • 1 Half

  • 4,582 SqFt
  • 0.20 Acres

Single Family / Villa

Bear's Den At Reunion

Under Construction. Contemporary And Modern With Custom Details In Every Room, This Home Is Featured In The Exclusive Gated Community Of Bears Den, “a Jack Nicklaus Licensed Community In Reunion.” Cool Porcelain Plank Floors Lead You Into An Expansive Kitchen With Quartz Counter Tops, Dining And Family Room Complete With A Stunning Stone Feature Wall Warmed By A Modern Fireplace. This Six Bedroom, 6.5 Bath Home Has Four Master Suites With Porcelain Tile Floors And A Beautiful Upstairs Game Room With A Full Bar And Private Balcony. Enjoy B...

2713 Formosa Blvd, Kissimmee

Price
Reduced
Photo of Listing #S4833802

$1,285,000

  • 9 Beds
  • 10 Baths
  • 1 Half

  • 8,198 SqFt
  • 0.33 Acres

Single Family / Villa

Formosa Gardens Unit 01

Huge Reduction Due To Retirement, Making This A Fantastic Opportunity For The Next Owner. This Stunning Luxury, Custom Built 9 Bedroom Villa Is One Of The Largest And One Of The Most Exclusive Vacation Villas In Formosa Gardens, With Over 9,500 Sq Ft. Of Living Area Featuring A Movie Room, Sports Room With Gymnasium And Pool Table, & 1500 Game Arcade Machine. There Is A Grand Piano, 2 Staircases, 120 Feet Of Balconies, Infinity Pool And Hot Tub Overlooking A Beautiful Lake Front. This Exquisite Villa Occupies A Prime Location In The Popular...

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...

1087 Jack Nicklaus Ct, Kissimmee

Photo of Listing #T2914504

$1,189,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 3,850 SqFt
  • 0.21 Acres

Single Family / Villa

Bear's Den At Reunion

Under Construction. Beautiful Modern Classic Home Located In The Exclusive Gated Community Of Bears Den, “a Jack Nicklaus Licensed Community In Reunion.” Bright And Welcoming With Lots Of Natural Light, This Five Bedroom, 5.5 Bath Home Is Accented With A Coastal Color Palette. Full Of Custom Features Inside And Out To Include Three Master Suites, Two With Private Balconies, Secluded Theater, Game Room With Engineered Wood Floors, Apron Sink, Porcelain Plank Floors In The Kitchen And Family Areas, And Quartz Counter Tops Throughout. Out...

2595 Michigan Ave, Kissimmee

Photo of Listing #S4858526

$999,997

  • 3 Beds
  • 2 Baths

  • 1,656 SqFt
  • 4.72 Acres

Single Family / Villa

Acreage & Unrec

Incredible Opportunity! This Property Is Zoned Institutional App. 5 Acres With App. 220 Ft Frontage On Michigan Ave. 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. Can Be Used For Educational Facilities (private), Hospital/health Institute, Houses Of Worship, Park And Playgrounds, Pet Rescue/veterinary, Endless Possibilities.

241 Falls Dr, Kissimmee

Photo of Listing #S4856880

$990,000

  • 11 Beds
  • 10 Baths
  • 3 Half

  • 5,436 SqFt
  • 0.21 Acres

Single Family / Villa

Reunion West Ph 2a West

The Most Beautiful Home At Encore. This Pristine South Facing Pool, 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 Downstair...

491 Burma St, Kissimmee

Photo of Listing #O5704104

$929,000

  • 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....

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.

7616 Brookhurst Ln, Kissimmee

Photo of Listing #O5700282

$875,000

  • 11 Beds
  • 10 Baths
  • 3 Half

  • 5,496 SqFt
  • 0.19 Acres

Single Family / Villa

Reunion West Ph 1

Fantastic Fully Furnished 11 Bedrooms, 10.3 Bathrooms Pool Home In Encore Resort. The Biltomore Floor Plan Is One Of The Best In The Resort. This Turnkey Home Features Many Great Leisure And Social Seating Areas . 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. Family Style Dining Table That Seats Up To 12 Family Members And Friends. The Outdoor Pool Area Has A Huge Deck Area Providing Sun During The Whole Day. This ...

7649 Wilmington Loop, Kissimmee

Photo of Listing #O5570159

$805,000

  • 9 Beds
  • 8 Baths
  • 1 Half

  • 4,630 SqFt
  • 0.15 Acres

Single Family / Villa

Reunion West Ph 1 West

This One Of A Kind Hawthorne Model Residence Is Located In The Encore Club At Reunion. First Impressions Are Everything, And This Property Does Not Disappoint With Features Such As Its Sleek And Modern Elevation And Cool And Stylish Color Palette. From The Moment You Enter This Exquisite Nine Bedroom, 8.5 Bath Vacation Home You Will Notice It Has Been Professionally Decorated By Lisa Sherry With Superior, Handpicked Furniture And Decor As Well As Custom Ceiling Fans, All Included In The Purchase Price. This Home Was Purposefully Designed Wit...

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.

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.

Listing information last updated on May 25th, 2018 at 10:30am EDT.