Kissimmee, 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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1,128 Properties Found. Showing Page 1 of 94
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$3,645,900
- 4
Beds
- 4
Baths
3,134
SqFt- 0.34
Acres
Single Family / Villa
Patricks Add
Price Reduced Seller Motivated!!! Look At This Property!!! This Property Is A Gem With No Hoa And Is Located In The Heart Of Our Historic Downtown Kissimmee. It Sits On A Corner Lot With Beautiful Oak Trees Surrounding The Property Allowing For Much Shade Throughout And Therefore Conserving Energy. This Lovely Home Was Built With The Potential To Be Converted Into A Duplex Or Mother-in-law Suite. It Shows 4 Bedrooms, 4 Baths, 2 Separate Entrances, 2 Separate Car Garages, 2 Separate Operating A/c Units, And A Nice Sized Driveway. The Kitchen...
$2,445,410
- 7
Beds
- 7
Baths
- 2
Half
7,142
SqFt- 0.32
Acres
Single Family / Villa
Reunion West Fairways 17...
Under Construction. This Remarkable 7 Bedroom, 7 Full Baths & 3 Half Baths Custom Home Will Feature A Master And Secondary Bedroom Downstairs, An Expansive Kitchen With A Super Island With Seating For 12, Two Refrigerators, Wine Refrigerator, Separate Dining Room As Well As A Movie Room, Game Room And 2 Laundry Rooms. You Will Find Ample Outdoor Areas To Relax In, Some Of Which Will Be A Covered Upstairs Balcony In The Front Of The Home, As Well As A Covered Balcony Upstairs At The Rear Of The Home, Covered Lanai With A Spectacular Pool Feat...
$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 ...
Price
Reduced
$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...
$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...
$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...
$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).
$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...
$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.
Price
Reduced
$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 ...
$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....
$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.
The 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.
Browse Kissimmee Holiday Home Communities:
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 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 July 18th, 2018 at 12:30pm EDT.
