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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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...

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 One Of A Kind Water Front Estate In Formosa Gardens Is Simply A Great Investment Opportunity With A Track Record Of Good Returns. To Some It's Known As The Wedding Estate, This Turn-key Home 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...

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...

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...

7604 Wilmington Loop, Kissimmee

Photo of Listing #O5824460

$1,250,000

  • 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...

7944 Jack Club Dr, Kissimmee

Photo of Listing #O5809691

$1,117,506

  • 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...

7940 Jack Club Dr, Kissimmee

Photo of Listing #O5815855

$1,087,900

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 4,913 SqFt
  • 0.21 Acres

Single Family / Villa

Bears Den

Under Construction. 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 Poo...

3085 Tindall Acres Rd, Kissimmee

Price
Reduced
Photo of Listing #O5807948

$1,025,000

  • 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...

1658 Marina Lake Dr, Kissimmee

Price
Reduced
Photo of Listing #O5816878

$1,000,000

  • 6 Beds
  • 5 Baths
  • 1 Half

  • 6,012 SqFt
  • 0.52 Acres

Single Family / Villa

Ashley Cove Un 2

Welcome To Your New Family Home, It’s All About The Location. From The Moment You Enter The Front Door, You’ll Be At Home In This 6 Bedroom, 5 And A Half Bathroom Family Home With 4 Car Garage. With Its Open Floor Plan, Well-equipped Kitchen And Fantastic Lake View From Both The Family Room And Patio Area, It’s An Entertainer's Dream Home. The Covered Boat Dock With Seating Area And Boat Lift Offers Access To Lake Toho And The Kissimmee Chain Of Lakes. Take Part In The World-renowned Bass Fishing Tournaments Or Simply Take A Sunset Cruise To...

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...

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 November 19th, 2019 at 12:46pm EST.