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!

Search Kissimmee Real Estate Listings

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
1,463 Properties Found. Showing Page 1 of 122
View As: Map
Sort by:

717 Eastlawn Dr, Kissimmee

Photo of Listing #O5508277


  • 8 Beds
  • 9 Baths
  • 1 Half

  • 8,473 SqFt
  • 0.47 Acres

Single Family / Villa

Celebration East Village...

Amazing Mediterranean Estate Pool Home With Extraordinary Water & Conservation Views In Celebration. Enjoy Over 8,000sf Of Pure Luxury, Starting With The Dramatic Entrance Of The House With The Spiral Staircase, Marble Entry And Throughout The House, Soaring Ceilings, You Will Not Find A House Like This One! You Will Enjoy An Open Floor Plan, Cozy Family Room, 8 Bedrooms, 7.5 Bathrooms, A Movie Theater That Has Its Own Grand Entrance And Top Of The Line Projector And Surround Sound, Office With Its Own Library, Amazing Outdoor Space With Wat...

2365 Thacker Trl, Kissimmee

Photo of Listing #S4841770


  • 7 Beds
  • 7 Baths
  • 1 Half

  • 7,829 SqFt
  • 5.54 Acres

Single Family / Villa

Happy Trails Unit 03 Unrec

Secluded Custom Built Estate Only Minutes From Champions Gate. Through The Gate, The Tropical Landscaping Welcomes You Onto Your Private, 5.54 Acres With A 786 Sq Ft Guest House And The 7,043 Sq Ft Main House, Which Offers 3 Living Rooms, 6 Bedrooms And 6½ Bathrooms. Entering The Massive 10 Ft Mahogany Front Doors, You Will Notice The Impressive Foyer With The Dramatic Custom Built Staircase, 22 Ft Soaring Ceilings With Oversized Windows Allowing In Exorbitant Amounts Of Light And The Travertine Flooring Throughout. In The Formal Living Room...

2713 Formosa Blvd, Kissimmee

Photo of Listing #S4833802


  • 9 Beds
  • 10 Baths
  • 1 Half

  • 7,600 SqFt
  • 0.33 Acres

Single Family / Villa

Formosa Gardens Unit 01

This Stunning Luxury 9 Bedroom Villa Is One Of The Largest And One Of The Most Exclusive Vacation Villas In Formosa Gardens, With Over 9,500 Sq Ft. Of Living Area Featuring A Movie Room, Sports Room With Gymnasium And Pool Table, & 1500 Game Arcade Machine. There Is A Grand Piano, 2 Staircases, 120 Feet Of Balconies, Infinity Pool And Hot Tub Overlooking A Beautiful Lake Front. This Exquisite Villa Occupies A Prime Location In The Popular Formosa Gardens Estates, Directly On The Lakefront With A South Facing Pool. It Is Undoubtedly One Of T...

1388 Grandview Blvd, Kissimmee

Photo of Listing #S4834258


  • 5 Beds
  • 5 Baths
  • 1 Half

  • 9,029 SqFt
  • 0.97 Acres

Single Family / Villa

Regal Point West

This Stunning Florida Inspired Estate Overlooks Lake Tohopekaglia. One Room Is Lovelier Than The Last With Fine Finishes Including Wood Floors, Rich Custom Cabinetry And Moldings, Brick Accents, Floor To Ceiling Windows, And Luxury Craftsman Designed Elements Throughout. Well -appointed Master Suite And A Guest Suite With Its Own Entrance Sit On Main Level. Chef’s Delight Of A Kitchen Has Its Own 3-way Fireplace, Large Island With Seating And Lake View Nook. Step Out To Screened Living Porch With Summer Kitchen To Further Appreciate The Spec...

1110 Watson Ct, Kissimmee

Photo of Listing #O5491041


  • 7 Beds
  • 7 Baths
  • 1 Half

  • 5,898 SqFt
  • 0.16 Acres

Single Family / Villa

Reunion Ph 1

Stunning New Completed Custom Designed 7 Bedroom Investment/residential Luxury Home With Pool And Spa, Theater Room, Game Room With Private Conservation Rear Located In Orlando’s Renowned Reunion Resort Is Ready For Immediate Possession. Custom Designed To Give A Delightful Yet Practical Ambiance, This Beautiful Home Offers Copious Outdoor Living And Bedroom Allocation Space Coupled With Well-implemented Luxury Features Such As The Private Movie Screening Room And Entertainment / Games Rooms. Large Open Plan Kitchen, Family And Dining Space...

N/A, Kissimmee

Photo of Listing #S4847045


  • 4 Beds
  • 4 Baths
  • 2 Half

  • 3,746 SqFt
  • 9.86 Acres

Single Family / Villa

A Gorgeous Equestrian Center Home With Almost 10 Acres Of Land With Over 3,740 Square Feet Of Living Space To Include Four Bedroom Suites. Beautiful Hardwood Floors Throughout This Home. Master Bedroom Has Plenty Of Room To Relax And Enjoy The Scenery. Immaculate Condition Home With Screened In Heated Pool For Outdoor Living. This Home Has A Beautiful Open Floor Plan For Entertaining Your Guests. Featuring Separate Guest House Next To The Main Home. All Property Is Fenced In With A Long Driveway Leading To Your New Home. For The Horse En...

404 S Vernon Ave, Kissimmee

New Photo of Listing #S4847801


  • 1 Beds
  • 2 Baths

  • 2,442 SqFt
  • 1.66 Acres

Single Family / Villa

Johnson Lillie Resub

Its All About Location Location Location!!! This Land Is Prime Position To Big Toho Marina And Lake Tohopekaliga. The 1.66 Acre Lot Is Great For Development With The Appropriate Planning Permissions And County Approval. Situated In Downtown Kissimmee It Is Easy Access To The Town, Restaurants, Bars, The Lake, Florida Turnpike And All Amenities. The Land Across The Parking Lot Is Being Developed Into A 1 & 2 Bedroom Apartment Complex. If You Clear The Trees And Foliage On This Lot You Are Right Opposite The Lake. Fabulous Opportunity Fo...

7935 Sea Pearl Cir, Kissimmee

Photo of Listing #S4845736


  • 7 Beds
  • 5 Baths

  • 3,337 SqFt
  • 0.64 Acres

Single Family / Villa


This Is A 7 Bedroom 5 Bathroom Pool And Spa Home With 4 Master Bedrooms In An Upscale Community Called Formosa Gardens Estates. Please View The Photo Page To View All Photos. The Property Has A Large South Facing Pool With An Over Size Pool Deck And Very Large Back Yard With No Homes Behind The Property. Comes Fully Furnished And With A Finished Games Room. Large Open Kitchen Over Looking The Living Room And Nook Area With Table As Viewed On The Photos. Large Dinning Room, All Nice Size Bedrooms With Flat Screen Tv's. Many Flat Screen Tv's T...

3620 Reaves Rd, Kissimmee

Photo of Listing #S4825314


  • 4 Beds
  • 3 Baths

  • 3,296 SqFt
  • 2.01 Acres

Single Family / Villa

Acreage & Unrec

Great Location In Growing Area And With 4 Bedrooms And 3 Baths It's Ready For Your Family To Move In And The Florida Lifestyle. Near Shopping, Restaurants, And Schools.

2701 Swoop Cir, Kissimmee

Photo of Listing #O5494818


  • 6 Beds
  • 3 Baths

  • 3,792 SqFt
  • 0.24 Acres

Single Family / Villa


Luxurious Fully Custom Modern Home! Built In 2013, At Almost 4,000 Sq Ft Of Living Space Within The Gated Community Of Avilla In Kissimmee, This Home Features 6 Bedrooms, 3.5 Baths. Fully Furnished! Exquisite Design Throughout And Top Of The Line Finishes. Upon Entrance Through The Beautiful French Glass Door, The Open Floor Plan Invites You Into The Spacious Living Room Soaring Two-story Ceilings To Create A Relaxed Ambiance For Relaxation, Overlooking The Sparkling, Infinity Pool Where You Can Enjoy The Fascinating Lake View And Amazing Su...

335 Oakhurst Cir, Kissimmee

Photo of Listing #O5462473


  • 6 Beds
  • 4 Baths

  • 6,500 SqFt
  • 2.14 Acres

Single Family / Villa

Oakhurst Estates

Escape To The Peace And Beauty Of Your Own Private And Secluded Estate. A Giant Oak Canopy And Circular Driveway Sets The Scene For This Magnificent Country Retreat. Large Residence Boasts 6 Bedrooms, Two Dens, Formal Living And Dining Rooms, Family Room With Fireplace And Soaring Ceilings, Bright And Lovely Sunroom, Basement Exercise Or Recreation Room, And A Project Room Off The Kitchen For Crafts, Sewing, And Laundry. Enormous Screened Pool And Lanai With Breathtaking Vistas Will Be The Backdrop For Your Life's Storybook. Property Include...

7657 Wilmington Loop, Kissimmee

Photo of Listing #S4847556


  • 10 Beds
  • 10 Baths

  • 4,723 SqFt
  • 0.18 Acres

Single Family / Villa

Reunion West Ph 1 West

7657 Wilmington Loop Is A Vacation Paradise!! New 10 Bed 10 Bath Home On An Oversized South East Facing Lot. Located In The Incredible Encore Club Resort You And Your Guests Will Have Access To Some Of The Best Amenities Orlando Has To Offer. These Include Huge 60 Ft Waterpark Quality Waterslides, Drop Tower, Pool, Aqua Park, Tennis, Basketball Court, Beach Volleyball, Weight Room, Restaurants, Bar, Meeting Rooms And More. The Home Is Being Sold Fully Furnished With Rentals In Place After Time Of Closing To Convey To New Owner If Same Manage...

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.

^ Back to: Kissimmee Real Estate

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.

Listing information last updated on June 26th, 2017 at 9:51am EDT.