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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1,326 Properties Found. Showing Page 1 of 111
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1045 Jack Nicklaus Ct, Kissimmee

Photo of Listing #O5711154


  • 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...

1051 Jack Nicklaus Ct, Kissimmee

Photo of Listing #O5711133


  • 7 Beds
  • 7 Baths
  • 1 Half

  • 5,410 SqFt
  • 0.18 Acres

Single Family / Villa

Reunion West Fairways 17...

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 Will Have 7 Bedrooms...

2960 Frontier Dr, Kissimmee

Photo of Listing #O5727356


  • 5 Beds
  • 4 Baths
  • 1 Half

  • 5,464 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...

3501 Harbor Rd, Kissimmee

Photo of Listing #S4856774


  • 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...

2617 Yountville Ave, Kissimmee

Photo of Listing #O5729884


  • 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...

2937 Tindall Acres Rd, Kissimmee

Photo of Listing #O5742817


  • 3 Beds
  • 3 Baths
  • 1 Half

  • 3,330 SqFt
  • 5.38 Acres

Single Family / Villa

Narcoossee N M

Secluded 5.38 Acre Lakefront Estate Situated On Fells Cove. From The Moment You Enter Through The Private Gate, You Feel At Peace With Nature As The Long Circular Drive Winds Through The Mature Oak And Pine Trees That Span The Property. Once Inside The Home, You Are Greeted By High Ceilings And Large Windows With An Abundance Of Natural Light In The Open Floor Plan. No Details Have Been Missed With This Home's High-end Finishes. From The Travertine Floors, With Solid Wood Inlay, To Jenn-air Appliances In The Kitchen, You Will Have Difficulty...

241 Falls Dr, Kissimmee

Photo of Listing #S4856880


  • 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 ...

1681 Gateway Ln, Kissimmee

New Photo of Listing #S5009825


  • 5 Beds
  • 5 Baths
  • 1 Half

  • 6,151 SqFt
  • 0.35 Acres

Single Family / Villa

Bella Lago

Enjoy The Fantastic Sunrise View Every Day From This Brand New Home On Lake! This 5/bed 5.5/bath Brand New Home Is Right On The Short Of Beautiful, World-famous Lake Tohopekaliga (‘lake Toho’)! Tons Of Upgrades Including Highest Upgraded Kitchen, Luxury Outdoor Kitchen, Wood Floor On The Entire Second Floor, Screened Backyard To Name A Few.... Bellalago Is A Gated Community Featuring A World Of Resort-caliber Amenities, From Recreation To Lakeside Dining: A 1,300-ft Boardwalk With A Gazebo That’s Picture-perfect For Strolling. The Boat Ra...

3620 Reaves Rd, Kissimmee

Photo of Listing #S4825314


  • 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.

335 Oakhurst Cir, Kissimmee

Photo of Listing #S5008305


  • 6 Beds
  • 4 Baths

  • 6,500 SqFt
  • 2.14 Acres

Single Family / Villa

Oakhurst Estates

If You Are Looking For A Place That Offers Country Living At Its Best, This Unique Development, Consist Of Only Four, Traditional Custom Brick Homes, Nestled Within Mature Trees And Lush Landscape. As You Drive Up, Your Private Circular Driveway Will Set The Scene For This One Of A Kind Country Retreat. This Majestic, 6 Bedrooms, Has Two Dens, Formal Living And Dining Rooms, Family Room With Double Sided Fireplace, Soaring Ceilings, A Few Feet Away A Bright And Lovely Sunroom Will Make You Smile. See Another Great Area For The Arts & Craf...

7697 Fairfax Dr, Kissimmee

Photo of Listing #T3121057


  • 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...

2701 Swoop Cir, Kissimmee

Photo of Listing #O5494818


  • 6 Beds
  • 3 Baths
  • 1 Half

  • 3,992 SqFt
  • 0.24 Acres

Single Family / Villa


Luxurious Fully Custom Modern Home! Built In 2013, At Almost 4,000 Sq Ft Of Living Space Within The Gated Community Of Avilla In Kissimmee, This Home Features 6 Bedrooms, 3.5 Baths. Exquisite Design Throughout And Top Of The Line Finishes. Upon Entrance Through The Beautiful French Glass Door, The Open Floor Plan Invites You Into The Spacious Living Room, Soaring Two-story Ceilings To Create A Relaxed Ambiance For Relaxation, Overlooking The Sparkling, Infinity Pool Where You Can Enjoy The Fascinating Lake View And Amazing Sunsets. The Slee...

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 November 17th, 2018 at 10:14am EST.