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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508 Properties Found. Showing Page 1 of 43
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8590 Apache Trail, KISSIMMEE

New Photo of Listing #O5898603


  • 5 Beds
  • 5 Baths
  • 4 Half

  • 11,138 SqFt
  • 5.00 Acres

Single Family Residence

Happy Trails Unit 05

If You Have Been Searching For An Exquisite Estate Home With The Utmost Of Privacy, This Is It. This Grande Estate Is A Rare Equestrian Find With 5 Acres. Conveniently Located To Disney World, You Will Feel Like You Have All The Seclusion But Easily Minutes To The Parks, Champions Gate Shopping, The 429 And To The Millennia Mall District. Boasting Over 12,000 Sf And Details That Are Rare To Find In Orlando Luxury Homes You Will Be Impressed With Craftsmanship And Attention To Detail. Double Iron Entry Doors Lead To A Welcoming Foyer And Your...

4441 Anderson Road, KISSIMMEE

New Photo of Listing #S5036295


  • 3 Beds
  • 2 Baths

  • 1,608 SqFt
  • 12.34 Acres

Single Family Residence

Acreage & Unrec

12.3 Acres !!!!investor Property !!!!perfect Location Right Off Of Us Hwy17/92 And Ham Brown In A Fast Growing Kissimmee Area! This Property Is Future Use Low Density Residential. Contains 2 Homes 1- Sfr With Pool And 1- Double Wide Modular Home, With 2 Barns, Workshops,rv Parking, Retention Pond And More! The Amenities And Locations Are Endless. The Main Home Contains 3 Bedrooms 2baths 1608 Sqft Heated! Plus A In Ground Pool To Enjoy! The 2nd Home Contains 4 Bedrooms 3 Full Baths, And Is Busting At The Seams At 2340 Ft.². This Whole Proper...

3200 Great Oaks Boulevard, KISSIMMEE

New Photo of Listing #O5911912


  • 6 Beds
  • 5 Baths
  • 1 Half

  • 5,667 SqFt
  • 6.00 Acres

Single Family Residence

Great Oak Unit 01

This 5 Bedroom, 6 Full And 2 Half Bathroom Custom Home On 5.71 Acres Is Available For The First Time. A Long Driveway Through Mature Trees Leads Up To The Front Of This Home. Unique Tilt Wall And I-beam Construction Make This One Of The Strongest Homes In The Area. Custom Woodwork, Solid Wood Doors, Storm Proof Shingles, Sprayed Insulation, Lightning Rods, Tankless Water Heaters, Are All Luxury Elements That Make This Home Special. The Front Entrance Patio Opens Into The Formal Living Room. Natural Light Fills This Space And Highlights ...

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...

7695 Graben Street, KISSIMMEE

New Photo of Listing #O5935934


  • 12 Beds
  • 12 Baths
  • 1 Half

  • 6,351 SqFt
  • 0.25 Acres

Single Family Residence

Reunion West Ph 2b West

This Turn-key Home Is Your Next Vacation Home Or Investment Property Allowing Short Term Rental Income. Located Just 10 Minutes From Disney The Spacious 12 Bedroom Home Has 12 Bathrooms, Most En Suite. This Home Provides A Luxurious Lifestyle Within The Exclusive Gated Community Of Encore Resort At Reunion. One Large Master Suites With Spa-like Soaker Tubs Are Located On The 1st Floor, Along With Additional 3 Bedrooms With Showers. Out The Back Lanai, Enjoy Year-round Use Of The Sparkling Pool And Spa. Upstairs, An Additional Game Area Is S...

217 Southfield Street, KISSIMMEE

New Photo of Listing #O5921371


  • 10 Beds
  • 9 Baths
  • 1 Half

  • 5,189 SqFt
  • 0.24 Acres

Single Family Residence

Reunion West Ph 4 Replat

Perfect Location! This Brand New And Never Used Two-story House Offers 10 Bedrooms, 9 Full Bathrooms, 1 Half Bathroom, And A 2 Car Garage. Located Close To The Club House, The House Features A Large Open Floor Plan With A Living/dining/kitchen Combo That Owners And Guests Will Love! It Is Perfect For Entertaining And Spending Vacation Time With Family And Friends. The Kitchen Has Two Double Refrigerators And Two Dishwashers And The Floor Plan Features Two Laundry Rooms, One In Each Level, Two Master Bedrooms, A Large Balcony On The Second Fl...

8525 Patricia Trail, KISSIMMEE

New Photo of Listing #O5931879


  • 6 Beds
  • 5 Baths
  • 1 Half

  • 5,157 SqFt
  • 5.01 Acres

Single Family Residence

Happy Trails Unit 03 Unrec

This Turnkey Magnificent Home Sits On Over 5 Acres Of Peaceful, Serene, Natural Beauty. Custom Built In 2017 This House Boasts Three Master Suits With Walk In Closets, Soak In Bathtubs Standalone Showers And Duel Sinks, It Also Has An Open Loft Area, High Ceilings, Large Windows, Sliding Glass Doors Opening Out From The Family Room And Downstairs Master Bedroom To The Huge Screened Pool And Spa In This Courtyard Style Setting. The Open Plan Kitchen Has Solid Wood Cabinets, Granite Countertops, Large Pantry, State Of The Art Appliances With...

221 Falls Drive, KISSIMMEE

New Photo of Listing #O5931568


  • 9 Beds
  • 8 Baths
  • 1 Half

  • 4,630 SqFt
  • 0.21 Acres

Single Family Residence

Reunion West Ph 2a West

Luxurious Fully Furnished Home In The Renowned Encore Resort. This Beautiful 9 Bedroom 9 Bathrooms Home Is Marked With Striking Yet Functional Elegance,4,630 Sf Under Air. Indulge And Entertain On A Grand Scale By The Stylish Pool Surrounded By Lush Landscaping Right Behind The Encore Club. Inside You Will Be Impressed With A Stunning Kitchen That Features Double Refrigerators, High Ceilings, Professionally Decorated Rooms And A Game Room, Which Are Just Some Of This Spectacular Property Highlights. Encore Resort Is Home To An Exemplary Wat...

229 Southfield Street, KISSIMMEE

New Photo of Listing #O5937064


  • 10 Beds
  • 9 Baths

  • 5,156 SqFt
  • 0.17 Acres

Single Family Residence

Reunion West Ph 4

Welcome To 229 Southfield Street, A Modern And Luxurious, Fully Furnished, Executive Style Property Located In The Exclusive Encore At Reunion Resort. As Soon As You Enter This Stunning Home, You Will Be Just Enthralled And Amazed At Just How Light And Spacious This Property Is Throughout. This Is Truly A Dream Home. Built In 2020, The Property Has Been Meticulously Furnished With Thoughtful Decorative Touches And Wall Accents Throughout. There Is Just Such A Vibrant And Joyful Atmosphere To This Home. The New Owners And Guests Will Just Fe...

7657 Wilmington Loop, KISSIMMEE

New Photo of Listing #S5048774


  • 10 Beds
  • 10 Baths

  • 4,723 SqFt
  • 0.18 Acres

Single Family Residence

Reunion West Ph 1 West

High Performing, Exceptionally Maintained, 10 Bed 10 Bath Home On An Over-sized South East Facing Lot With Easy Walking Distance To The Clubhouse, And Amenities. Located In The Spectacular Encore Club Resort You And Your Guests Will Have Access To Some Of The Best Amenities Orlando Has To Offer. These Include A Huge Water Park, Exhilarating Water Slides, Drop/splash Tower, Enormous Pool, Aqua Park, Tennis Courts, Basketball Court, Beach Volleyball, Weight Room, Restaurants, Full Service Bar, Meeting Rooms And More. The Home Is Being Sold Ful...

2815 Spinning Silk Court, KISSIMMEE

New Photo of Listing #S5043236


  • 7 Beds
  • 7 Baths
  • 1 Half

  • 6,562 SqFt
  • 0.34 Acres

Single Family Residence

Formosa Gardens Unit 01

Back On The Market! This Luxurious Custom Built Home Located In The Gated Community Of Formosa Gardens Features Many Upgrades. The House Boasts A Great Floor Plan With 7 Master Bedrooms Each With Their Own Bathrooms. The Entrance Of The Home Is Grand With Mosaic Tiles, Large Pillars And Volume Ceilings. The Staircase Has Wrought Iron Rails. The Downstairs Master Bathroom Boasts A Walkthrough Shower With Beautiful Tiles, Upgraded Cabinets And Tray Ceilings. The Large Kitchen Has Upgraded Maple Cabinets With Granite Countertops And Built In Ap...

2612 Yountville Avenue, KISSIMMEE

New Photo of Listing #O5918509


  • 14 Beds
  • 11 Baths

  • 6,255 SqFt
  • 0.21 Acres

Single Family Residence

Sonoma Res/tapestry-ph 1

Back To The Market .the Loan Fell Through. The Sought After Guard Gated Community At Sonoma Resort Built By Park Square Homes! This Massive Resort Home Features 14 Bed Rooms.a Home Fit For Any Family, You Will Find Not 1, But 2 First Floor Master Suites Each With Its Own Master Bath. Designed With Multiple Families In Mind, The House Is Guaranteed To Be The Solution To Finding The Vacation Home Of Your Dreams! The Spacious Island Kitchen And Dining Nook Conveniently Located Near The Large Great Room. Adding To The Inspired, Open-concept Feel...

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 April 19th, 2021 at 4:48am EDT.