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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1,247 Properties Found. Showing Page 1 of 104
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2481 Ham Brown Road, KISSIMMEE

New Photo of Listing #O6015144

$3,500,000

  • 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...

510 Golfpark Drive, KISSIMMEE

New Photo of Listing #S5071094

$2,400,000

  • 6 Beds
  • 5 Baths
  • 1 Half

  • 5,547 SqFt
  • 0.27 Acres

Single Family Residence

Celebration Village Unit 02

A Rare Find In Celebration, As Homes On The Exclusive "golf Park Drive" Do Not Come Up For Sale Too Often. This Luxury Home Boasts Front Porch Views Of The 18th Fairway Of The Celebration Golf Course, With No Homes Across The Street, Giving An Added Sense Of Privacy. Easy Walking Distance To The Restaurants Of Downtown Celebration Makes This The Perfect Blend Of Convenient Access And Tranquil Privacy. The Backyard Features An Oversized Pool, Perfect For Larger Families, And The Firepit, Built-in Summer Kitchen And Granite Bar Allow For A ...

4421 Reaves Road, KISSIMMEE

New Photo of Listing #S5031594

$2,200,000

  • 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...

8025 Surf Street, KISSIMMEE

New Photo of Listing #O6046954

$1,895,000

  • 7 Beds
  • 7 Baths

  • 4,212 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 5

Do Not Miss Out On The Opportunity To Grab Your Very Own Piece Of Paradise. This Waterfront Spacious 7 Bedroom 7 Full Bathroom Cottage Is Located In The Famous Margaritaville Resort Orlando. This Floor Plan Is Unique And Offers So Much Space And Completed With Tile Flooring Throughout. The Kitchen Is Huge With Large Island, Quartz Countertops, Open To The Living Areas And Formal Dining Room. Private Pool And Spa Which Has Access To A Full Bath. The Second Floor Includes A Nice Spacious Loft With Balcony That Overlooks The Pool And Pond. The...

831 Oak Shadows Road, KISSIMMEE

New Photo of Listing #S5066465

$1,895,000

  • 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...

1830 Kings Highway, KISSIMMEE

New Photo of Listing #S5072279

$1,800,000

  • 9 Beds
  • 7 Baths
  • 1 Half

  • 12,460 SqFt
  • 5.03 Acres

Single Family Residence

Fla Drained Land Co Sub

You Must See This Masterpiece Of A Home! This Dream Home Has Everything You Need. From Lots Of Space To A Great Location To Even Housing Animals! Located Next To The Delightful And Famous Kissimmee Lakefront Park, This One-of-a-kind Home Is An Actual Work Of Art! One Of The First Things To Mention About The Property Is How Much Land There Is. This Property Has Over Five Acres Of Land! Yes, You Read That Correctly, Over Five Acres Of Land! Enjoy All The Land You Could Ever Want! You Can Also Split Three Acres And Sell Them Separately To A Min...

8101 Surf Street, KISSIMMEE

New Photo of Listing #O6046251

$1,788,800

  • 7 Beds
  • 7 Baths

  • 4,212 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 6a

Beautiful And Spacious Waterfront Cottage With Pool, Spa And Gorgeous West-facing Sunset Views! Huge 4218-a Model With 7 Bedrooms And 7 Full Bathrooms, Upgraded High-end Metal Roof, Pelican Water Treatment System And Custom Plantation Shutters On First And Second Floors (cost $10,000)! ‘in Paradise’ Upgrades Including 'wood' Tile Floors And Quartz Countertops Throughout Entire Home. This Amazing Home Features Two Bedrooms On First Floor, Large Kitchen With A Huge Island, Large Cabinets, Spacious Pantry, New Kitchen Aid Dishwasher, Upgraded ...

348 Southfield Street, KISSIMMEE

New Photo of Listing #O6041743

$1,750,000

  • 13 Beds
  • 12 Baths
  • 1 Half

  • 6,351 SqFt
  • 0.37 Acres

Single Family Residence

Reunion West Ph 4

World-famous Encore Resort At Reunion, Just South Of Disney. Very Successful Vacation Rental With Current Bookings To Transfer To New Owner. A Spacious 13 Bedrooms And 12.5 Bathrooms, Fully Furnished, A Chefs Gourmet Kitchen With Stainless Steel 2 Refrigerators, Double Ovens, And Microwave On Quartz Counters And Beautiful Tiled Backsplash. The Kitchens Oversized Island Has Double Sinks, Wide Breakfast Bar And All Part Of The Master Great Room Where There Is Room For Everyone And Easy For Guest Entertainment. The Wide Slider To The Back Cover...

3084 Parrot Head Place, KISSIMMEE

New Photo of Listing #O6017418

$1,699,000

  • 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 With Multiple Patio Sliders And Lots Of Natural Light! 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 S...

4201 Paragraph Drive, KISSIMMEE

New Photo of Listing #O6051978

$1,500,000

  • 8 Beds
  • 5 Baths

  • 4,289 SqFt
  • 0.13 Acres

Single Family Residence

Cove/storey Lk Iv

Newly Built 8 Bed Home In Sought After Storey Lake!! Premium Lot With Water View!! Fully Furnished, Never Occupied

3050 Partin Settlement Road, KISSIMMEE

New Photo of Listing #O6041024

$1,500,000

  • 10 Beds
  • 7 Baths
  • 1 Half

  • 6,602 SqFt
  • 1.95 Acres

Single Family Residence

Acreage & Unrec

This Is Your Opportunity To Own Part Of A Compound In Kissimmee! This Lot Has 2 Homes On It. This Property Can Be Sold Individually But Is Also Offered To Be Sold With 3 Other Lots, All Connected. Please See Listings O6041029, O6041026, And O6041023. These 4 Lots Are All Being Sold Together For $3.1 Million. The First Home Is A Spanish Style 4 Bed/2.5 Bath Home Featuring A Beautiful Front Porch! Once You Enter, There Is A Formal Living And Dining Area To Your Left And The Master Bedroom Straight Ahead. To Your Right Is The Spacious Family Ro...

212 South Clyde Avenue, KISSIMMEE

New Photo of Listing #O6015808

$1,500,000

  • 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...

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 DBA Stellar MLS.

Listing information last updated on August 19th, 2022 at 12:48am EDT.