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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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

This Exceptional Custom Built 8,100+ Sq. Ft. Mediterranean Style Estate Is Less Than 2 Miles Away As A Crow Flies From Animal Kingdom And One Of A Kind In Gated Formosa Gardens Estates.this Is A Turn-key Investment Closest To Disney Being Sold Exquisitely Furnished And Equipped For Those Orlando Theme Park Lovers Who Appreciate Nice Things And Can Afford Them. Everyone Loves Disney Even The Pampered, Enjoy Viewing Disney’s Fireworks From The All Of The Waterfront Upstairs Balconies Or From The 55 Foot Heated Infinity Swimming Pool & Spa. Thi...

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...

8450 Natures Hammock Trail Trl, Kissimmee

Photo of Listing #O5805321

$1,495,000

  • 1 Beds
  • 1 Baths

  • 5,600 SqFt
  • 5.01 Acres

Condo / Apartment

Na

Under Construction. Here Is Your Once In A Lifetime Chance At Owning Your Own Resort Within Driving Distance Of Disney World. Imagine The Potential Cash Flow For Years To Come As You Are Able To Create Lifetime Memories For Your Guests Night In And Night Out In This Exclusive Resort. With 4 Buildings, And 6 Different Housing Combinations You Will Always Have Occupancy. This Resort Features It's Own Private Lake, Walking Trail, Swimming Pool, No Hoa. It's A Ready Made Business For You. Scheduled To Be Completed In March 2020, Seller Will Cons...

3064 Parrot Head Pl, Kissimmee

Photo of Listing #O5802963

$1,250,000

  • 8 Beds
  • 9 Baths
  • 1 Half

  • 4,480 SqFt
  • 0.08 Acres

Single Family / Villa

Rolling Oaks Ph 5

Magnificent Margaritaville Cottage For Sale On Mro's Trophy Row! Check Out The 3d Virtual Tour And Video! Breathtaking Balcony Views From Both Second And Third Floors! Enormous Top Floor Wrap Around Balcony! Unobstructed Views Of The Beautiful Sunset Every Night Overlooking The Large Lake And Resort! Located Within Easy Walking Distance To All The Resort Amenities! 2 Bedrooms On First Floor, 5 Bedrooms On Second Floor And Master Suite On Top Floor. Stunning Truly Unique One-of-a-kind Masterpiece Floor Plan Not Being Built In Future Phases! ...

3085 Tindall Acres Rd, Kissimmee

Price
Reduced
Photo of Listing #O5807948

$1,200,000

  • 4 Beds
  • 4 Baths
  • 2 Half

  • 5,600 SqFt
  • 8.00 Acres

Single Family / Villa

Narcoossee New Map

Welcome Home To This Breathtaking Secluded Piece Of Nature Featuring Two Full Custom Block Homes With A Hefty List Of Upgrades And Luxury Touches-- This Property Has The Natural State Park Feel With Its Pre-cut Nature Trails And Wooded Seclusion That Really Opens Ups For The Ultimate Lake View Paradise Lifestyle--wake Up In The Am And Take Your Personal Private Morning Coffee Walk Or Golf Cart Ride While Enjoying The Sun Rise And Sun Set---heres A List Of Features Be Sure To See Video On Youtube -- 3085 Tindall Acres Rd -- -- 8-/+ Total Ac...

7948 Jack Club Ct, Kissimmee

Photo of Listing #O5809698

$1,146,300

  • 6 Beds
  • 6 Baths
  • 1 Half

  • 4,705 SqFt
  • 0.21 Acres

Single Family / Villa

Bears Den

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...

7944 Jack Club Dr, Kissimmee

Photo of Listing #O5809691

$1,106,300

  • 6 Beds
  • 5 Baths
  • 1 Half

  • 4,395 SqFt
  • 0.21 Acres

Single Family / Villa

Bears Den

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...

2613 Yountville Ave, Kissimmee

Photo of Listing #S5023051

$1,100,000

  • 14 Beds
  • 11 Baths

  • 6,255 SqFt
  • 0.21 Acres

Single Family / Villa

Sonoma Res/tapestry Ph 1

Let The Party Begin In This Massive 6,255 Square Foot Resort Home Features 14 Bedrooms, 11 Baths And A 3-car Garage. A Home Fit For A King, You Will Find Not 1, But 2 First Floor Master Suites Each With Its Own Master Bath. Further Enhancing The Space On First Floor, 3 Guest Bedrooms And 3 Guest Baths Will Be Ideal For Any Family Member Or Guest. Designed With Multiple Families In Mind, The Second Floor You Will Be Pleasantly Surprised To Find A Third Master Suite With Its Own Private Master Bath. In Addition, 8 Spacious Guest Bedrooms And...

1389 Grandview Lot 6 Blvd, Kissimmee

Photo of Listing #O5803109

$999,000

  • 4 Beds
  • 3 Baths
  • 1 Half

  • 4,000 SqFt
  • 2.74 Acres

Single Family / Villa

Regal Point Unit 02

Pre-construction. To Be Built. Don’t Miss Your Chance To Own Your Custom Dream Home On This Beautiful 2.78 Acre Lakefront Property In The Highly Sought-after Regal Point Executive Community! Buyers Can Select Upgrades And Colors And/or Make Modifications To Floor Plan Or Start The Design Process From Scratch As This Home Has Not Finished Permitting... Call Today! Located On West Lake Toho And Nestled On A Small Peninsula, The Property Features Expansive Western Views Offering Beautiful Sunsets And Views Of The Disney Fireworks At Night! West...

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...

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...

N/A, Kissimmee

Price
Reduced
Photo of Listing #S5019915

$949,000

  • 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...

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 September 18th, 2019 at 1:15am EDT.