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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4441 Anderson Rd, Kissimmee

Photo of Listing #S5026748

$3,000,000

  • 4 Beds
  • 4 Baths

  • 1,608 SqFt
  • 12.34 Acres

Single Family / Villa

Acreage & Unrec

One Or More Photo(s) Has Been Virtually Staged. Beautiful Property Right Off 17-92 And Ham Brown In The Fast-growing Kissimmee Area! With Just Under 13 Acres, This Property Contains Two Homes (one Sfr With Pool And One Doublewide Mobile Home), Three Barns/outbuildings, Rv Parking, Retention Pond And More! With Ham Brown Frontage, The Possibilities Are Endless! The Main Home Contains 3 Bedrooms, 2 Baths, 1,608sf, And An In-ground Pool. The Second Home Contains 4 Bedrooms, 3 Full Baths, And Boasts 2,340 Sf. With Fencing, Workshops, Cattle Corr...

4445 Austin Rd, Kissimmee

Photo of Listing #S5026767

$2,500,000

  • 3 Beds
  • 2 Baths

  • 1,560 SqFt
  • 8.02 Acres

Single Family / Villa

Acreage & Unrec

Come View This Great Property Located Just Off 17-92 And Ham Brown Rd. With Ham Brown Access, This Lot Contains Just Over 8 Acres Of Serenity. The Property Contains A Block, Sfr With 3 Bedrooms, And 2 Baths, As Well As A Separate Single Wide Mobile Home Containing 1,064sf. Zoned For Horses And Other Agricultural Options, With An Additional Barn/workshop, This Property Is A Must-see!

21 E Lakeshore Blvd, Kissimmee

Photo of Listing #O5828006

$2,375,000

  • 6 Beds
  • 7 Baths
  • 2 Half

  • 9,328 SqFt
  • 3.49 Acres

Single Family / Villa

Florida Fruit Belt Sales Co

Wow!! Welcome To Your Private, Gated, Lakefront Mansion Residing On Nearly 4 Acres Of Fenced In Land, With Your Own Tennis/basketball Court And Private Dock To Lake East Toho. This Magnificent Estate Is Truly One Of A Kind And Definitely Makes A Statement! Enjoy Entering This Compound Through Your Own Private Gate, Winding Down Your Long, Circular Paver Driveway Surrounded By Huge Palm Trees And Lush Landscaping. This 9,328 Sf Estate Boasts 6 Bedrooms, 7 Full Baths, 2 Half Baths, 4 Car Garage, Private Heated Pool & Spa, Huge Covered Lanai An...

N/A, Kissimmee

Photo of Listing #S5027998

$2,300,000

  • 5 Beds
  • 6 Baths
  • 1 Half

  • 4,485 SqFt
  • 0.21 Acres

Single Family / Villa

Fractional Ownership. Note: This Property Is An Exclusive Turnkey Income Producing Opportunity For Fractional Ownership. Buyer May Purchase All 4 Units Or Individual Units. Prices Starting At $239,000 To $289,000 The Jack Nicklaus Residence Club At Bear’s Den Provides Access To 3 Golf Courses, A Tennis Complex, Water Park, Restaurants And Community Events. The Impressive Clubhouse Features A Club Restaurant, Patio Seating, Fully Stocked Pro Golf Shop, Men’s And Women’s Locker Rooms, And A Well-equipped Exercise Room. Owners, Guests And...

2713 Formosa Blvd, Kissimmee

Photo of Listing #O5795273

$1,650,025

  • 9 Beds
  • 10 Baths
  • 1 Half

  • 8,198 SqFt
  • 0.33 Acres

Single Family / Villa

Formosa Gardens Unit 01

Now $173,917.88 Booking Monies Going To The New Owners If They Were To Close By Feb 15th 2020, These Are All Owner Bookings Not Paying Commissions To A Booking Agency Or Pm. This Turn-key Estate Is 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 Upstairs Balconies Or From The 55 Foot Heated Infinity Swimming Pool. It Has Hand Crafted Ceilings, Custom Lighting, Polished Porcelain ...

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...

7937 Sea Pearl Cir, Kissimmee

Photo of Listing #S5024681

$1,575,000

  • 7 Beds
  • 8 Baths
  • 1 Half

  • 9,128 SqFt
  • 0.42 Acres

Single Family / Villa

Formosa Garden Un 02

The Ultimate Vacation Home! This Custom-built Home Using The Icf Building Method Stands At Over 9000 Sq Ft. It Needs To Be Seen To Be Believed. No Expense Has Been Spared By The Current Owners In Creating This Unique Home – Currently Offered As A Vacation Rental With A Strong And Established Client Base And Many Future Bookings Its Equally Suited As A Luxury Family Estate Home. The First Floor Offers A Highly Flexible Space With Huge Custom Kitchen, High End Appliances, Stunning Family Room, Games Room, Private Movie Theater, Office/8th B...

N/A, Kissimmee

Photo of Listing #S5028016

$1,466,669

  • 6 Beds
  • 6 Baths
  • 3 Half

  • 5,231 SqFt
  • 0.18 Acres

Single Family / Villa

Fractional Ownership. Note: This Property Is An Exclusive Turnkey Income Producing Opportunity For Fractional Ownership. Buyer May Purchase All 4 Units Or Individual Units. Prices Starting At $239,000 To $289,000 The Jack Nicklaus Residence Club At Bear’s Den Provides Access To 3 Golf Courses, A Tennis Complex, Water Park, Restaurants And Community Events. The Impressive Clubhouse 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 Rente...

7985 Sea Pearl Cir, Kissimmee

Photo of Listing #S5024669

$1,295,000

  • 7 Beds
  • 8 Baths
  • 1 Half

  • 7,907 SqFt
  • 0.33 Acres

Single Family / Villa

Formosa Gardens Unit 01

This Custom -built Home Of Nearly 8000 Sq. Ft Was Built By The Current Owners With No Expense Spared Throughout. Designed As A Purpose- Built Luxury Vacation Rental It Comes Backed With A Strong Rental History With Many Future Bookings And Repeat Clients Or Would Equally Make A Stunning Family Home. Every Bedroom Is Its Own Luxury Suite With Private Bathrooms And Seating Areas. The Bathrooms All Feature High End Finishes, Full Height Luxury Tiles And Italian Vanity Units. Downstairs The Custom Kitchen With Steel Appliances And Huge Famil...

8450 Natures Hammock Trail Trl, Kissimmee

Price
Reduced
Photo of Listing #O5805321

$1,195,000

  • 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. With Estimated A...

7604 Wilmington Loop, Kissimmee

Price
Reduced
Photo of Listing #O5824460

$1,175,000

  • 13 Beds
  • 12 Baths
  • 1 Half

  • 6,351 SqFt
  • 0.21 Acres

Single Family / Villa

Reunion West Ph 1

Biggest Short Term Rental Floor Plan On The Market And Great Rental Performance! Beautiful 13 Bedrooms 12.5 Bathrooms In The Encore At Reunion Community Just A Short Walk From The Water Park, Tennis Court, Fitness And Restaurants! This Contemporary Home Is Tastefully Furnished And Has A Beautiful Home Theater With Leather Recliners And A Wet Bar Upstairs Close To The Loft Area To Help You Relax After A Long Day At The Parks. The Spacious Breakfast Bar Is Great For A Big Family Or Group To Enjoy The Morning Time Together. The Central Living A...

8081 Surf St, Kissimmee

Photo of Listing #O5818359

$1,149,000

  • 7 Beds
  • 7 Baths

  • 4,218 SqFt
  • 0.08 Acres

Single Family / Villa

Rolling Oaks Ph 5

Amazing Margaritaville Resort Orlando Cottage Resale In The First Phase 'sunset Cove' Closest To The Resort Amenities! Huge 4218-a Model, 7 Bedrooms And 7 Bathrooms With Master Bedroom On Second Floor With Walk In Closet, Back Patio With In-ground Pool And Spa That Overlooks Lake And Awesome Sunsets!! Loft On Second Floor And Bonus Room On Third Floor. Plenty Of Room To Install A Wet Bar If Desired! Upgraded Appliances, Kitchen Countertops And Flooring. In-ceiling Speakers In Living Room That Connects To Tv Or Phone Via App! List Price Inclu...

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 January 17th, 2020 at 6:45am EST.