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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631 Properties Found. Showing Page 1 of 53
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900 Jack Nicklaus Court, KISSIMMEE

New Photo of Listing #O6018108


  • 8 Beds
  • 10 Baths
  • 2 Half

  • 9,558 SqFt
  • 0.55 Acres

Single Family Residence

Reunion West Fairways 17...

If You Are Looking For Two Of The Most Iconic Homesites In Arguably The Best Location In Reunion Resort Look No Further! This Exquisitely Finished 8 Br Custom Build Inside The Exclusive Gates Of The Bear's Den Adjacent To Traditions Clubhouse Will Fulfill Every Desire. This Home Makes An Immediate Statement From The Soaring 25' Porcelain Tiled Grand Foyer Entryway And Custom Mural Adorned Walls Through To The Great Room And Kitchen On Your Way To The Huge Back Expanse Of This Double Lot With Its Infinity Edge Pool And Breathtaking Views Th...

2481 Ham Brown Road, KISSIMMEE

New Photo of Listing #O6015144


  • 3 Beds
  • 2 Baths

  • 2,800 SqFt
  • 15.71 Acres

Single Family Residence

Acreage & Unrec

Private Acreage Right Off Ham Brown Road In Fast Growing Kissimmee Area With Its Own Private Driveway To The Immaculately Kept 2,800 Sq Ft Home. If You Love The Peaceful And Quiet Countryside, But Still Need To Be Near Amenities, This Is The Perfect Location For You. This Can Be Your Own Quiet And Serene Piece Of Paradise Right Outside Of The City. Enjoy Easy Access To The Best Shopping, Restaurants, Theme Parks, Hospitals And More Just Within A Short Ride Down The Street! The 15.71-acres Are Currently Zoned As Agricultural. A Serene Pond Is...

942 Jack Nicklaus Court, KISSIMMEE

New Photo of Listing #O6019853


  • 8 Beds
  • 8 Baths
  • 2 Half

  • 5,720 SqFt
  • 0.22 Acres

Single Family Residence

Reunion West Fairways 17...

This Is A Phenomenal Opportunity Inside Our Exclusive Bear's Den Subdivision! This Beautiful Residential Home Will Make An Easy Transition For High Rental Income In One Of The Most Sought After Areas In Reunion. This 8br Custom Build Has Everything You Need For Success. 3 Bedrooms Downstairs And 5 Up Accompanied By A Perfectly Situated & Dedicated Movie Theater And Media Room. The Lot Is Exquisite If You Like Never Ending Sunsets And A Fantastic Covered Lanai With A Fully Equipped Outdoor Kitchen And Lounge Area. Fully Furnished With Tr...

4445 Austin Road, KISSIMMEE

New Photo of Listing #O5979928


  • 3 Beds
  • 2 Baths

  • 2,624 SqFt
  • 8.02 Acres

Single Family Residence

Acreage & Unrec

Possibilities Are Endless. This Is A Remarkable Opportunity For An Investor/builder Looking To Develop A Small New Subdivision Of Single-family Homes, Townhomes, Duplexes, Etc., Or This Is Your Chance To Own A Small Paradise For Your Own Private Residence. This Is A Beautiful, Tucked Away From Traffic Lot, A Little Over 8 Acres. The Property Currently Includes A 3 Bedroom, 2 Bath Home, A Separate Single Wide Mobile Home, A Horse Paddock, Fenced In Horse Field And A Barn/workshop. At This Time, Property Is Zoned As Agricultural Which Can Be E...

4421 Reaves Road, KISSIMMEE

New Photo of Listing #S5031594


  • 5 Beds
  • 5 Baths
  • 1 Half

  • 5,044 SqFt
  • 41.01 Acres

Single Family Residence

Bobbie Jean Acres

This Stunning, Custom Designed And Custom Built Home Is A Once In A Lifetime Opportunity. Imagine Yourself Driving In Through The Private Gated Entrance, Past The Serene Pond, And Up To The Perfectly Landscaped Front Yard. This Home Has All The Little Details You Could Ask For: Crown Molding, Additional Recessed Lighting, Built Ins, Study Nooks, And Many Architectural Touches Throughout. Walk Into The Formal Living Room With Windows That Let The Florida Sunlight Stream In. The Spacious, Open Kitchen Boasts Both A Bar With Seating And An Isla...

831 Oak Shadows Road, KISSIMMEE

New Photo of Listing #S5066465


  • 6 Beds
  • 5 Baths
  • 1 Half

  • 4,673 SqFt
  • 0.27 Acres

Single Family Residence

Celebration East Village

Gracious Living Can Be Yours In This Amazing, Custom Home Built By Issa Homes. Oversized Double Porches Overlook A Conservation Area. The Backyard Affords Privacy As Lush Landscaping Surrounds A 45 Ft. Lap Pool, Hot Tub, Large Back Porch, & Deck. Nice! Extensive Landscaping Gives The Feel Of A Tropical Paradise! Ten French Doors Lead Out To The Oversized Front Porch & Second-story Balcony And Music Is Piped Inside & Outside The Home! The 6th Bedroom Was Designed As A Theatre Room - It Is Acoustically Designed & Wired For Projection. Addition...

3084 Parrot Head Place, KISSIMMEE

New Photo of Listing #O6017418


  • 5 Beds
  • 5 Baths

  • 3,578 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 5

'the Shark Tank' Is A Spectacular Waterfront Cottage With Pool, Spa And Gorgeous Sunset Views On Margaritaville Resort Orlando's 'trophy Row'! Premier Resort Location Just Steps From The Fins Up Beach Club And Other Resort Amenities! Fantastic Opportunity To Own One Of The Largest And Rarest Floor Plans, This Spacious 3579-c Two-story Model Features 5 Bedrooms, 5 Full Bathrooms, The "beach House" Upgrade Package And A Large Patio/balcony On Both Floors! This Amazing Home Features Two En Suite Bedrooms On First Floor, Kitchen With Large Islan...

8097 Surf Street, KISSIMMEE

New Photo of Listing #O6017827


  • 8 Beds
  • 9 Baths
  • 2 Half

  • 4,092 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 6a

Wow! Come To Margaritaville .....stay And Play Or Enjoy A Full Time Resort Style Life. This 8 Bedroom, 9 Full Bath And 2 Half Bathrooms, Pool/spa Home Is Spread Over 3 Levels And Totaling 4092 Sqft. Enjoy Lounging, Sun Bathing And Bbq's On Your Pool Deck With A Cabana Bathroom For Convenience. This Home Is Fully Furnished By City Furniture And Designed With The " Son Of The Sailor" Package. The Huge Master Bedroom Suite On The 2nd Floor Has A Built In Closet And A Safe. Walk Out To The Spacious Balcony Overlooking The Pool, Big Pond And Perh...

212 South Clyde Avenue, KISSIMMEE

New Photo of Listing #O6015808


  • 4 Beds
  • 3 Baths

  • 4,292 SqFt
  • 0.56 Acres

Single Family Residence

Patricks Add

Own A Piece Of History In Beautiful Downtown Kissimmee. Fall In Love With This Charming 4 Bedrooms And 3 Bathrooms With Just Under 4,500 Sq Ft Colonial Home, With Eye-catching Details Around Every Corner. Drive Up To A Circle Driveway In Front Of The Steps Up To Your Wrap Around Porch And Enter The Front Doorway To Step Into Time… 1925. The Doors Open To A Charming Foyer Leading You Up To A Wood Staircase Surrounded By Beautiful Wood Moldings On Doors And Walls, 10.5’ Ceilings And Pine Hardwood Floors Throughout The Home. To Your Left, T...

1126 Watson Court, KISSIMMEE

New Photo of Listing #O5952176


  • 8 Beds
  • 7 Baths
  • 1 Half

  • 4,606 SqFt
  • 0.16 Acres

Single Family Residence

Reunion Ph 1 Prcl 1 #2

Under Construction. New Construction Vacation Rental Home In Reunion Resort. 9 Bedroom, 8.5 Bedroom Located In The Watson Court Area Of Reunion Resort.

2050 South Cheryl Court, KISSIMMEE

New Photo of Listing #O6025413


  • 4 Beds
  • 2 Baths

  • 2,320 SqFt
  • 5.14 Acres

Single Family Residence

Bluegrass Estates Unit 01

Move To Sunny Florida! Serene Property That Has 4 Bedrooms, 2 Bathrooms With A Beautiful Screened-in 30/15 In-ground Pool With A Large 45x28 Sq Ft Patio Area On A 5.14 Acre Parcel Of Land, Located On A Cul-de-sac. It Features: 2 Detached Studios And An Unfinished One Bed 21x20 Sq Ft Guest House. The Main House Has A 10x6 Sq Ft Foyer, The Living Room Has Vaulted Ceilings With Skylights For Extra Lighting, A Family Room, A Separate Dining Room, An Spectacular Fully Renovated Kitchen That Overlooks The Pool Area, New Cabinets, New Quartz Count...

3811 Bowfin Trail, KISSIMMEE

New Photo of Listing #S5064781


  • 6 Beds
  • 4 Baths

  • 4,565 SqFt
  • 0.24 Acres

Single Family Residence

Bellalago Ph 4k

Welcome To The Spectacular, Mediterranean Style, *6 Bedroom / 4 Bathroom Pool Home* Nestled In A Premium *waterfront Lot With Boat Dock* In Bellalago, An Upscale And Man-gated Master Planned Community, With Access To Lake Tohopekaliga One Of Nine In The Kissimmee Chain Of Lakes Through A Gateway To Over 300 Inland Lakes And Waterways For Fishing And Boating. Be Amazed By This Former Park Square Model Home, Including All Available Upgrades And Features And Filled With Natural Light Distributed Throughout 4,565 Sqft Of Ample Living Spaces, O...

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 DBA Stellar MLS.

Listing information last updated on May 22nd, 2022 at 9:48am EDT.