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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1,197 Properties Found. Showing Page 1 of 100
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2713 Formosa Blvd, Kissimmee

Photo of Listing #O5795273

$1,650,000

  • 9 Beds
  • 10 Baths
  • 1 Half

  • 8,198 SqFt
  • 0.33 Acres

Single Family / Villa

Formosa Gardens Unit 01

Enter The Private Gates Of Formosa Gardens Estates To See This Magnificent Mediterranean Style Water Front Home. This Exceptional 8,100+ Square Foot Estate Is Custom Built And Is One Of A Kind In Formosa. It Has Been And Is Currently Being Used As An Investment Vacation Rental Because Of Its Proximity To Disney World Less Than 2 Miles As A Crow Flies From Animal Kingdom. This Is A Turn-key Investment Being Sold Exquisitely Furnished And Fully Equipped For Those Orlando Theme Park Lovers Who Like And Can Afford Nice Things “everyone Goes To D...

9054 Paolos Place, Kissimmee

Photo of Listing #O5794605

$1,650,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 6,312 SqFt
  • 1.64 Acres

Single Family / Villa

Westside Calabria

Luxurious Lakefront Living, Within The Shadows Of Walt Disney World®, Securely Positioned Behind Its Own Private Gates Within A Picturesque Neighborhood. Welcome To Paolos Place: A Heavenly Oasis Close To The Magic But Peaceful Enough To Be Its Own Destination. This Elegant Mansion Was The Neighborhood Builders' Personal Residence And Packed With Upgrades: Smart Home Technology, Soaring Ceilings, Custom Millwork, Tray Ceilings, And An Expansive Floorplan For Living And Entertaining – Set Within A Private Park-like Compound. Mixing Mediterran...

985 Jack Nicklaus Ct, Kissimmee

Photo of Listing #O5776619

$1,427,300

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 4,485 SqFt
  • 0.21 Acres

Single Family / Villa

Reunion West Fairways 17...

Under Construction. Under Construction. The Bear’s Den At Reunion Has Access To 3 Golf Courses, A Tennis Complex, Water Park, Restaurants And Community Events. The Impressive Clubhouse At Bear’s Den Features A Club Restaurant, Patio Seating, Fully Stocked Pro Shop, Men’s And Women’s Locker Rooms, And A Well-equipped Exercise Room. Owners, Guests And Renters At The Bear’s Den Club Will Have Access To Reunion’s 5-star Dining, 3 Championship Golf Courses, Golf Academy, Tennis, Playground, Spa, Water Park And 11 Community Pools! Exceptional Ho...

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...

404 S Vernon Ave, Kissimmee

Photo of Listing #P4906226

$985,000

  • 3 Beds
  • 2 Baths

  • 2,442 SqFt
  • 1.66 Acres

Single Family / Villa

Johnson Lillie Resub

Beautiful 1.66 Acre Site In Walking Distance To Restaurants, Entertainment, The Courthouse And All That Historic Downtown Kissimmee Has To Offer. The Lot, Which Includes A 2,442 Sq. Ft. Original Wood Frame House Built In 1894, Sits Directly Across The Street From Big Toho Marina With 238' Fronting Lakeshore Blvd. 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). So Many Possibilities With This Property. Remodel The Existing House And Use...

N/A, Kissimmee

Photo of Listing #S5019915

$975,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 4,966 SqFt
  • 0.55 Acres

Single Family / Villa

Colonial Style Two Story On Just Over ½ An Acre Of Land With Your Own Personal Pond And A View Of Woods. Covered Front Patio Offers French Door Access Into The Home You’ve Dreamed Of Your Entire Life. Wood Flooring, Soaring Ceilings, Decorative Ceilings, And So Much More! Office Space Is Currently Being Used As A Game Room But Would Be Great As A Play Area, Craft Room Or Anything Else That May Come To Mind. The Entry Leads To The Elegant Wooden Stairway, And Sitting Area That Opens To The Kitchen, Complete With Crown Molding, Decorative Cher...

251 Falls Dr, Kissimmee

Price
Reduced
Photo of Listing #S5012107

$969,000

  • 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...

2612 Yountville Ave, Kissimmee

Photo of Listing #O5770919

$950,000

  • 14 Beds
  • 11 Baths

  • 6,255 SqFt
  • 0.17 Acres

Single Family / Villa

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 Fe...

7721 Banyon Way, Kissimmee

Price
Reduced
Photo of Listing #S5016481

$925,000

  • 11 Beds
  • 10 Baths
  • 3 Half

  • 5,496 SqFt
  • 0.24 Acres

Single Family / Villa

Reunion

This Amazing 11 Bed Biltmore Home Is Located In The Encore Club With Its Spectacular Water Park, Plunge Slides, Restaurant, Bar And Other Fantastic Amenities, Including Child Care, Just 6 Miles From Disney Making It The Perfect Family Home Or Rental Vacation Property. Its Uniquely Positioned As It Has A Huge Pool, Spa & Sunny Deck Over Looking Green Area And Lake At The Rear, Giving A Magnificent Outlook. This Home Has An Open Plan Concept For Todays Easy Living, With A Large Kitchen With Granite Breakfast Bar And Stainless Steel Appliances....

7715 Banyon Way, Kissimmee

Price
Reduced
Photo of Listing #O5757786

$914,900

  • 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, ...

241 Falls Dr, Kissimmee

Price
Reduced
Photo of Listing #O5763001

$899,900

  • 11 Beds
  • 10 Baths
  • 3 Half

  • 5,496 SqFt
  • 0.21 Acres

Single Family / Villa

Reunion West/ Encore

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...

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...

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 July 21st, 2019 at 5:15pm EDT.