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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1,280 Properties Found. Showing Page 1 of 107
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9054 Paolos Pl, Kissimmee

Photo of Listing #O5767219

$1,690,000

  • 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 Two Living Areas & Formal Dining Area. Windows Abound Allowing The Natural Beauty Of The Outdoors To Be Enjoyed Throughout The Home. The Cu...

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...

3971 Oakville Ave, Kissimmee

Photo of Listing #O5764426

$1,149,000

  • 10 Beds
  • 10 Baths
  • 1 Half

  • 6,404 SqFt
  • 0.29 Acres

Single Family / Villa

Sonoma Res/tapestry Ph 1

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 Peace And Relaxation! It Boasts Style And Functionality With An Open Concept, Two Game Rooms, 10 Sui...

7605 Wilmington Loop, Kissimmee

Photo of Listing #S5010998

$1,100,000

  • 11 Beds
  • 10 Baths
  • 3 Half

  • 5,496 SqFt
  • 0.20 Acres

Single Family / Villa

Reunion West Ph 1

Well Appointed, Spacious Eleven Bedroom Home Located In The Fun Filled Encore Club Resort. Complete Turn Key Scenario Being Sold Fully Furnished W/ All Furniture And Furnishings. This Is A Prime Opportunity For A Personal Vacation Home, Investment Property Or Both! Located Within Easy Walking Distance To All The Fantastic Amenities & Features The Resort Has To Offer Such As A Aqua Park With Twisting Water Slides, Interactive Water Features And Massive Zero Entry Pool; State-of-the-art Clubhouse With A Full Service Restaurant And Bar; Fitness...

2937 Tindall Acres Rd, Kissimmee

Price
Reduced
Photo of Listing #O5742817

$999,900

  • 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...

251 Falls Dr, Kissimmee

Photo of Listing #S5012107

$985,000

  • 11 Beds
  • 10 Baths
  • 3 Half

  • 5,436 SqFt
  • 0.21 Acres

Single Family / Villa

Reunion

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 Home Theatre With Leather Recliners As Well As A Large Projection Screen. You And Your Family Can En...

241 Falls Dr, Kissimmee

Photo of Listing #O5763001

$949,000

  • 11 Beds
  • 10 Baths
  • 3 Half

  • 5,496 SqFt
  • 0.21 Acres

Single Family / Villa

Reunion West

Whether You’re Looking For A Sizeable Primary Residence Or A Vacation Home That Can Accommodate Even The Largest Of Families, You’ve Found It! Boasting 11 Bedrooms, 10 Full Baths, 3 Half Baths And Over 5,400 Square Feet Of Living Space This Property Is Located On A Fantastic Lot Featuring Stunning Views And Easy Access To The Amazing Community Water Park! This Home Is Completely Turn-key The Only Thing Needed Is You! You’ll Enjoy A Huge Great Room With A Dining Table That Easily Seats 12, Your Kitchen Showcases A Modern Backsplash, Stainless...

7715 Banyon Way, Kissimmee

Photo of Listing #O5757786

$949,000

  • 11 Beds
  • 10 Baths
  • 3 Half

  • 5,496 SqFt
  • 0.22 Acres

Single Family / Villa

Encore Resort

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 Racing Water Slides And Drop Slides, Fitness Center, Splash Pad, Basketball Courts, Restaurant & Bar, ...

335 Oakhurst Cir, Kissimmee

Photo of Listing #S5008305

$899,000

  • 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...

1681 Gateway Ln, Kissimmee

Price
Reduced
Photo of Listing #S5009825

$895,000

  • 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...

7697 Fairfax Dr, Kissimmee

Price
Reduced
Photo of Listing #T3121057

$885,000

  • 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...

7616 Brookhurst Ln, Kissimmee

Price
Reduced
Photo of Listing #O5700282

$825,000

  • 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 With Cinema Room . 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...

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 March 25th, 2019 at 1:45am EDT.