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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222 Pawnee Trail, KISSIMMEE

New Photo of Listing #P4922879

$5,900,000

  • 3 Beds
  • 3 Baths
  • 2 Half

  • 6,559 SqFt
  • 5.00 Acres

Single Family Residence

Happy Trails Unit 04

With Breathtaking Sunset And Golf Course Views, This 5-acre, One-of-a-kind Lot Is Where Your Florida Dream Home Will Be Built. 356 Feet Of The Lot Fronts On Champions Gate's National Golf Course, One Of Two Championship 18-hole Golf Courses, Designed By Accomplished Architect And Golfer, Greg Norman. Your Backyard Oasis Has Magnificent Views Of The 14th Hole And 15th Tee Box Without The Expense Of Large Hoa Dues. This Home Is Within Happy Trails, An Equestrian Community. The Community Has Limited Construction Restrictions, Which Allows M...

2481 Ham Brown Road, KISSIMMEE

New Photo of Listing #O6015144

$3,500,000

  • 3 Beds
  • 2 Baths

  • 2,800 SqFt
  • 15.71 Acres

Single Family Residence

Acreage & Unrec

Private Acreage Right Off Ham Brown Road In Fast Growing Kissimmee Area With Its Own Private Driveway To The Immaculately Kept 2,800 Sq Ft Home. If You Love The Peaceful And Quiet Countryside, But Still Need To Be Near Amenities, This Is The Perfect Location For You. This Can Be Your Own Quiet And Serene Piece Of Paradise Right Outside Of The City. Enjoy Easy Access To The Best Shopping, Restaurants, Theme Parks, Hospitals And More Just Within A Short Ride Down The Street! The 15.71-acres Are Currently Zoned As Agricultural. A Serene Pond Is...

906 Jack Nicklaus Court, KISSIMMEE

New Photo of Listing #O6066876

$3,200,000

  • 8 Beds
  • 8 Baths
  • 2 Half

  • 5,590 SqFt
  • 0.18 Acres

Single Family Residence

Bears Den

Our Pine Valley Model Overlooking The 18th Fairway Of The Jack Nicklaus Golf Course In Reunion, Florida. This Spacious Home Is Steps Away From The Club House And Large Enough To Enjoy With Family And Friends. This Beautiful Home Offers 8 Bedrooms / 8 Full And 2 Half Baths, Game Room, Movie Room, Summer Kitchen Overlooking The Golf Course And Club House. Reunion Resort Is Conveniently Located 5 Miles From Disney Parks And Disney Springs. Close To The Airport. Reunion Also Features 3 Golf Courses Designed By Golf Greats Jack Nicklaus, Tom...

510 Golfpark Drive, KISSIMMEE

New Photo of Listing #S5071094

$2,400,000

  • 6 Beds
  • 5 Baths
  • 1 Half

  • 5,547 SqFt
  • 0.27 Acres

Single Family Residence

Celebration Village Unit 02

A Rare Find In Celebration, As Homes On The Exclusive "golf Park Drive" Do Not Come Up For Sale Too Often. This Luxury Home Boasts Front Porch Views Of The 18th Fairway Of The Celebration Golf Course, With No Homes Across The Street, Giving An Added Sense Of Privacy. Easy Walking Distance To The Restaurants Of Downtown Celebration Makes This The Perfect Blend Of Convenient Access And Tranquil Privacy. The Backyard Features An Oversized Pool, Perfect For Larger Families, And The Firepit, Built-in Summer Kitchen And Granite Bar Allow For A ...

8165 Surf Street, KISSIMMEE

New Photo of Listing #S5073570

$2,275,000

  • 8 Beds
  • 9 Baths

  • 4,672 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 6a

Welcome To The Sought-after Cottages Of Margaritaville! As You Walk Into Your Beautiful Front Door Be Emersed In The Light Flowing Through Your Open Floor Plan Oasis. You Will Instantly Feel The Luxurious Feeling Of Being On Vacation In This 8-bedroom 9 Bathroom Sail Away Themed Home. Every Bedroom In This Masterpiece Has An Ensuite Bathroom! Two Bedrooms Greet You On The First Floor And Just Outside Your Backdoor, Be Captivated By Your Private Pool And Spa. The Second-floor Wows With 5 Bedrooms. The 3rd Floor Has 1 Bedroom, A Sitting Area,...

8073 Surf Street, KISSIMMEE

New Photo of Listing #O6071066

$2,200,000

  • 8 Beds
  • 9 Baths
  • 2 Half

  • 4,582 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 5

Immaculate ~ Never Been Rented ~ Spacious ~ Waterfront Cottage With Pool, Spa And Spectacular West-facing Sunset Views! Rare Third Floor Full Wrap Around Balcony! 7 Year A/c Warranty Transferable To Buyer! Huge 4480-b Model With 8 Bedrooms, 9 Full And 2 Half Bathrooms And Large Media Room! High-end Mro Approved Ethan Allen "son Of Sailor” Furniture/housewares Package Included In List Price! This Amazing Home Features Two Bedrooms On First Floor, Large Island Kitchen, Tall Cabinets And A Spacious Pantry, Great For Entertaining! Wooden Bar Fur...

4421 Reaves Road, KISSIMMEE

New Photo of Listing #S5031594

$2,200,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 5,044 SqFt
  • 35.63 Acres

Single Family Residence

Bobbie Jean Acres

This Stunning, Custom Designed And Custom Built Home Is A Once In A Lifetime Opportunity. Imagine Yourself Driving In Through The Private Gated Entrance, Past The Serene Pond, And Up To The Perfectly Landscaped Front Yard. This Home Has All The Little Details You Could Ask For: Crown Molding, Additional Recessed Lighting, Built Ins, Study Nooks, And Many Architectural Touches Throughout. Walk Into The Formal Living Room With Windows That Let The Florida Sunlight Stream In. The Spacious, Open Kitchen Boasts Both A Bar With Seating And An Isla...

2812 Sleeping Dragon Lane, KISSIMMEE

New Photo of Listing #S5075102

$2,000,000

  • 8 Beds
  • 8 Baths

  • 6,072 SqFt
  • 0.51 Acres

Single Family Residence

Formosa Gardens Un 2

Custom Built Home Specifically Designed For Today’s Family Vacation Rental Business Approximately 3 Miles From Walt Disney World. Turn Key Business With Future Transferable Rentals In Place And One Of The Best Rental Histories In The Resort Area. 8 Bedrooms, 7 Of Which Are Suites With Private Baths. Talk About Curb Appeal. As You Enter The Circular Driveway With Mature Tropical Landscape The 7000 Square Foot Home Including Covered Porches Rises From The Large Manicured Front Lawn. Double Doors Enter Into A Two Story Foyer With Office To The ...

1830 Kings Highway, KISSIMMEE

New Photo of Listing #S5072279

$1,800,000

  • 9 Beds
  • 7 Baths
  • 1 Half

  • 12,460 SqFt
  • 5.03 Acres

Single Family Residence

Fla Drained Land Co Sub

You Must See This Masterpiece Of A Home! This Dream Home Has Everything You Need. From Lots Of Space To A Great Location To Even Housing Animals! Located Next To The Delightful And Famous Kissimmee Lakefront Park, This One-of-a-kind Home Is An Actual Work Of Art! One Of The First Things To Mention About The Property Is How Much Land There Is. This Property Has Over Five Acres Of Land! Yes, You Read That Correctly, Over Five Acres Of Land! Enjoy All The Land You Could Ever Want! You Can Also Split Three Acres And Sell Them Separately To A Min...

8101 Surf Street, KISSIMMEE

New Photo of Listing #O6046251

$1,738,888

  • 7 Beds
  • 7 Baths

  • 4,212 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 6a

Price Just Reduced To Allow For $50k Towards Buyer's Brand New Furniture Package Of Their Choice! Rare, Beautiful And Spacious Waterfront Cottage With Pool, Spa And Spectacular West-facing Sunset Views Over The Water! Huge 4218-a Model With 7 Bedrooms And 7 Full Bathrooms And Lots Of Closets (more Than Any Other Model At The Resort)! Upgraded High-end Metal Roof, Pelican Water Treatment System And Custom Plantation Shutters On First And Second Floors (cost $10,000)! Property Has Been Used Exclusively As Primary Residence, Never Been Rented A...

8025 Surf Street, KISSIMMEE

New Photo of Listing #O6046954

$1,720,000

  • 7 Beds
  • 7 Baths

  • 4,212 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 5

Price Improvement!!! Turnkey! Do Not Miss Out On The Opportunity To Grab Your Very Own Piece Of Paradise. This Waterfront Spacious 7 Bedroom 7 Full Bathroom Cottage Is Located In The Famous Margaritaville Resort Orlando. This Floor Plan Is Unique And Offers So Much Space That Can Accommodate The Entire Family. The Kitchen Is Huge With Large Island, Quartz Countertops, Open To The Living Areas, Formal Dining Room, Completed With Tile Flooring Throughout. Private Pool And Spa Which Has Access To A Full Bath. The Second Floor Includes A Nice Sp...

3801 Sonoma Boulevard, KISSIMMEE

New Photo of Listing #S5075698

$1,550,000

  • 14 Beds
  • 11 Baths

  • 6,404 SqFt
  • 0.33 Acres

Single Family Residence

Sonoma Res/tapestry Ph 1

Location, Location, Location!!! Amazing Opportunity For Investors! This Is An Amazing Property For Short Term Rentals On Airbnb, Vrbo, Expedia, Booking.com Or In Your Own Website!!! This Luxury Villa With 14 Bedrooms/ 11 Bathrooms, Private Pool And Spa Was Park Square Homes Model Home On A Corner Lot Size:14.505 Sqft!!! With Uppgrades, Beautiful Walls, Lamps And More, This Property Offers To Investors A World Of Possibilities To Generate Great Income In The Best Touristic Place In The World Hosting Families And Friends' Gatherings Or Your...

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 December 9th, 2022 at 9:03pm EST.