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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573 Properties Found. Showing Page 1 of 48
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8590 Apache Trail, KISSIMMEE

New Photo of Listing #O5898603


  • 5 Beds
  • 5 Baths
  • 4 Half

  • 11,138 SqFt
  • 5.00 Acres

Single Family Residence

Happy Trails Unit 05

If You Have Been Searching For An Exquisite Estate Home With The Utmost Of Privacy, This Is It. This Grande Estate Is A Rare Equestrian Find With 5 Acres. Conveniently Located To Disney World, You Will Feel Like You Have All The Seclusion But Easily Minutes To The Parks, Champions Gate Shopping, The 429 And To The Millennia Mall District. Boasting Over 12,000 Sf And Details That Are Rare To Find In Orlando Luxury Homes You Will Be Impressed With Craftsmanship And Attention To Detail. Double Iron Entry Doors Lead To A Welcoming Foyer And Your...

918 Jack Nicklaus Court, KISSIMMEE

New Photo of Listing #O5952941


  • 6 Beds
  • 7 Baths
  • 1 Half

  • 8,299 SqFt
  • 0.40 Acres

Single Family Residence

Reunion West Fairways 17...

A Palatial 2-storey Home Located In Bears Den, A Jack Nicklaus Golf Course Community, With A Sprawling Green Vista. This One Of A Kind Custom-built Stunning Home With 6 Suites And 7 And Half Bathrooms Will Absolutely Take Your Breath Away! Designed By An Exceptional Team Of Architects And Interior Designers, This Contemporary Masterpiece Provides A Gorgeous And Spacious Home With Luxury Finishes And Features. Upon Entering, An Expansive Foyer Spills Into Soaring Open Living Space With Abundant Natural Light Flowing Through Tall And Wide Wind...

2960 Frontier Drive, KISSIMMEE

New Photo of Listing #O5966089


  • 5 Beds
  • 4 Baths
  • 1 Half

  • 5,464 SqFt
  • 10.10 Acres

Single Family Residence

Pine Oaks

Unique 10.1 Acre Estate In The Perfect Location For Privacy, Convenience And Fun! Beautiful Country Setting With Private Access To East Lake Tohopekaliga. Property Features The Main House, A Guest House, Storage/animal Shed And A Workshop. The Main House Of 4,187 Sq. Ft. Features 3 Bedrooms, 3.5 Baths, A Large Family Room With A Gas Fireplace And Pool Table, Large Kitchen With Plenty Of Cabinetry And Counter Space, Upgraded Stainless Steel Appliances And Beautiful Stone Accents. This Home Has A Very Large Screened-in Pool With An Island, Ove...

4421 Reaves Road, KISSIMMEE

New Photo of Listing #S5031594


  • 5 Beds
  • 5 Baths
  • 1 Half

  • 5,044 SqFt
  • 41.01 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...

8109 Surf Street, KISSIMMEE

New Photo of Listing #O5971870


  • 8 Beds
  • 9 Baths
  • 2 Half

  • 4,090 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 6a

Gorgeous Waterfront Cottage With Pool And Spa In Margaritaville! Sensational Sunset Views Over The Lake! Builder Model On Corner Lot With Large Side Yard Space And Tiki Hut! Upgraded High-end Metal Roof! Spacious 3-story 4090 Model With 8 Bedrooms, 9 Full Bathrooms, 2 Half Bathrooms, 2 Balconies And Bonus Loft On 3rd Floor! This Large Floor Plan Features 4 Bedrooms On The First Floor And 4 Bedrooms On The Second Floor. All Bedrooms Have En Suite Bathrooms And Ceiling Fans. Cottage Features Quartz Countertops, Upgraded Side-by-side Appliances...

7604 Wilmington Loop, KISSIMMEE

New Photo of Listing #O5971716


  • 13 Beds
  • 12 Baths
  • 1 Half

  • 6,351 SqFt
  • 0.21 Acres

Single Family Residence

Reunion West Ph 1

Welcome To The World-famous Reunion At Encore Resort, A 24-hour Man-gated Community That Features World Of High-end Amenities Near The World Disney World Resort. This Community Offers Resort-style Swimming Pools, A Giant Water Park, Award-winning Restaurants, A Concierge, And Plenty Of Other Fun Activities. This Magnificent 13 Bed/12 Bath Model Features A Spacious Living Space With An Open Floor Plan, And It's Fully Furnished With High-end Furnitures And Decors. Brand New Flooring Just Putted In For New Owner. Upon Entering The Beautifully ...

7704 Westland Drive, KISSIMMEE

New Photo of Listing #O5974427


  • 10 Beds
  • 9 Baths

  • 5,138 SqFt
  • 0.17 Acres

Single Family Residence

Reunion West Ph 4

This 10 Bedroom Is Located At The Encore Club, Less Than A 10 Minute Drive To Walt Disney World And Their Four Amazing Theme Parks! The Private Patio With A Swimming Pool And Spillover Spa Is The Perfect Way To Enjoy Florida's Sunshine And The Home Theater Is The Only Way To Relax After Long Days At The Theme Parks Where You And Your Loved Ones Can Watch Your Favorite Movies Together! Main Living Area: Spacious Comfortable Seating Area With 3x Sofas Overlooking The Private Pool Deck Through Sliding Glass Doors Kitchen: Fully Equipped W...

1087 Jack Nicklaus Court, KISSIMMEE

New Photo of Listing #O5975008


  • 5 Beds
  • 5 Baths
  • 1 Half

  • 3,850 SqFt
  • 0.21 Acres

Single Family Residence

Reunion West Fairways 17...

Stunning Reunion Pool Home In Bear’s Den On Desirable Park Corner Lot, With Active And Transferable Golf And Resort Membership! One Owner, Never Rented. Gorgeous Resort Style, Gas Heated And Salt Water Pool With Outdoor Summer Kitchen, Phantom Screens, Travertine Pavers, Fully Fenced With Masonry Walls And Dining Area. Location, Location, Location! Handpicked Home Situated On Private Park. Walk Your Dog Or Exercise On Your Street’s Own Gated Private Oasis. Home Is Loaded With Improvements! 12- 14 Ft Ceilings, Coffered Ceiling, Engineered Woo...

271 Falls Drive, KISSIMMEE

New Photo of Listing #S5056509


  • 11 Beds
  • 10 Baths
  • 3 Half

  • 5,496 SqFt
  • 0.32 Acres

Single Family Residence

Reunion West

Larger Lot At The Encore On A Model Biltmore 11 Bedrooms And 10 Bathrooms And 3 Half Bathrooms With 2 Car Garage + 6 Car Driveway With Heated Pool And Spa Inside The Encore Resort At Reunion. Lots Of Upgrades!!! One Of The Largest Lots Inside The Encore Resort At Reunion With 0.32 Acres Furniture Is Included (price Is With The Furniture, Beautifully Decorated With Premium Furniture) A Must See!!!

1654 Marina Lake Drive, KISSIMMEE

New Photo of Listing #W7817766


  • 5 Beds
  • 4 Baths

  • 4,141 SqFt
  • 0.62 Acres

Single Family Residence

Ashley Cove Un 2

Bass Fisherman's Paradise!!! Just Acquired-additional .62 Acre Adjacent Lot Total 1.2 Acres On Lake Tohopekaliga. Plenty Of Room To Build Your Toy Garage! This Beautiful Mediterranean Style Home Is Nestled Among The Grand Oaks Lakeside On Big Lake "toho"pekaliga, One Of The Top Rated Big Bass Lakes In The Usa. Part Of Florida's Chain Of Lakes, You Can Go Through The Lock System Through More Amazing Fishing Lakes To Lake Okeechobee And Then Exit Out To The Atlantic Ocean Or The Gulf Of Mexico! Enjoy All Of The Best Boating Waters Of Flo...

7657 Wilmington Loop, KISSIMMEE

New Photo of Listing #S5048774


  • 10 Beds
  • 10 Baths

  • 4,723 SqFt
  • 0.18 Acres

Single Family Residence

Reunion West Ph 1 West

High Performing, Exceptionally Maintained, 10 Bed 10 Bath Home On An Over-sized South East Facing Lot With Easy Walking Distance To The Clubhouse, And Amenities. Located In The Spectacular Encore Club Resort You And Your Guests Will Have Access To Some Of The Best Amenities Orlando Has To Offer. These Include A Huge Water Park, Exhilarating Water Slides, Drop/splash Tower, Enormous Pool, Aqua Park, Tennis Courts, Basketball Court, Beach Volleyball, Weight Room, Restaurants, Full Service Bar, Meeting Rooms And More. The Home Is Being Sold Ful...

2613 Yountville Avenue, KISSIMMEE

New Photo of Listing #O5973146


  • 14 Beds
  • 11 Baths

  • 6,255 SqFt
  • 0.21 Acres

Single Family Residence

Sonoma Res/tapestry Ph 1

Welcome To The High End Exclusive Florida Vacation Lifestyle. This Is A Fabulous, Luxurious Home Home And This Wonderful Vacation Property In The Sonoma Resort, Amazing High End Facilities And Security Gated Developments, With Disney On Your Doorstep... Not Only Is This An Amazing Large Home With Wonderful Extended And Upgraded West Facing Pool, You Are Also Only Minutes Walk To The High End Community Facilities Of This Five Star Vacation Resort.... This Grand 14 Bedroom -11 1/2 Bathroom Pool Home With Multiple King Size Master Bedrooms Has ...

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 September 27th, 2021 at 6:04am EDT.