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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8590 Apache Trail, KISSIMMEE

New Photo of Listing #O5898603

$5,000,000

  • 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...

4441 Anderson Road, KISSIMMEE

New Photo of Listing #S5036295

$2,300,000

  • 3 Beds
  • 2 Baths

  • 1,608 SqFt
  • 12.34 Acres

Single Family Residence

Acreage & Unrec

12.3 Acres !!!!investors Property !!!!perfect Location Right Off Of 17 -192 And Ham Brown In A Fast Growing Kissimmee Area! This Property Contains 2 Homes 1- Sfr With Pool And 1- Double Wide Modular Home, With 2 Barns, Workshops,rv Parking, Retention Pond And More! The Amenities And Locations Are Endless. The Main Home Contains 3 Bedrooms 2 Baths 1608 Sqft Heated! Plus A In Ground Pool To Enjoy! The 2nd Home Contains 4 Bedrooms 3 Full Baths, And Is Busting At The Seams At 2340 Ft.². This Whole Property Is Completely Fenced. Barn Is 60 Wide...

3200 Great Oaks Boulevard, KISSIMMEE

New Photo of Listing #O5911912

$2,250,000

  • 6 Beds
  • 5 Baths
  • 1 Half

  • 6,432 SqFt
  • 6.00 Acres

Single Family Residence

Great Oak Unit 01

This 5 Bedroom, 6 Full And 2 Half Bathroom Custom Home On 5.71 Acres Is Available For The First Time. A Long Driveway Through Mature Trees Leads Up To The Front Of This Home. Unique Tilt Wall And I-beam Construction Make This One Of The Strongest Homes In The Area. Custom Woodwork, Solid Wood Doors, Storm Proof Shingles, Sprayed Insulation, Lightning Rods, Tankless Water Heaters, Are All Luxury Elements That Make This Home Special. The Front Entrance Patio Opens Into The Formal Living Room. Natural Light Fills This Space And Highlights ...

4421 Reaves Road, KISSIMMEE

New Photo of Listing #S5031594

$2,200,000

  • 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...

930 Jack Nicklaus Court, KISSIMMEE

New Photo of Listing #S5044311

$2,095,000

  • 4 Beds
  • 4 Baths
  • 3 Half

  • 5,161 SqFt
  • 0.22 Acres

Single Family Residence

Reunion West Fairways 17...

*active Membership To The Reunion Club* A Magnificent Custom Contemporary Residence Located In The Exclusive Private Bears Den Club At Reunion Resort And Offered Fully Furnished. Ideally Situated On The Approach Of The 18th Green Of The Jack Nicklaus Signature Golf Course, This Home Enjoys Spectacular Views Down The Fairway And Over The Green With A West-facing Conservation View Backdrop Over Which The Sun Sets Majestically Each Night. Perfection. The Home Is Centered Around An Open And Expansive Gathering Room Where The Sweeping Cambria Qua...

2413 Rama Drive, KISSIMMEE

New Photo of Listing #O5917125

$1,775,000

  • 14 Beds
  • 14 Baths
  • 1 Half

  • 6,762 SqFt
  • 0.21 Acres

Single Family Residence

Veranda Palms Ph 2b2-2c

Be Prepared To Experience The Home Of A Lifetime. The Mission To Space Vacation Home! This Unique Home Is Among The Most Sought-after Vacation/gateway Homes In The Area. The Bedrooms Feature 14 Different Space Themed Rooms, Along With 14.5 Bathrooms. The Space Themed Rooms Take You On A Journey To Experience The Full-galaxy Like Never Before. Each Room Features A Space Related Experience, From The Apollo Missions, Man’s First Landing On The Moon And The Wonder Of The Galaxy, And So Much More. It Will Be Hard To Choose A Room! This Vacation V...

2409 Rama Drive, KISSIMMEE

New Photo of Listing #O5917089

$1,775,000

  • 14 Beds
  • 14 Baths
  • 1 Half

  • 6,762 SqFt
  • 0.19 Acres

Single Family Residence

Veranda Palms Ph 2b2-2c

Be Prepared To Experience The Home Of A Lifetime. The Mission To Space Vacation Home! This Unique Home Is Among The Most Sought-after Vacation/gateway Homes In The Area. The Bedrooms Feature 14 Different Space Themed Rooms, Along With 14.5 Bathrooms. The Space Themed Rooms Take You On A Journey To Experience The Full-galaxy Like Never Before. Each Room Features A Space Related Experience, From The Apollo Missions, Man’s First Landing On The Moon And The Wonder Of The Galaxy, And So Much More. It Will Be Hard To Choose A Room! This Vacation...

2713 Formosa Boulevard, KISSIMMEE

New Photo of Listing #S5037621

$1,599,900

  • 9 Beds
  • 10 Baths

  • 8,198 SqFt
  • 0.33 Acres

Single Family Residence

Formosa Gardens Unit 01

Exquisite Vacation Luxury Lake Front Home Awaiting Your Arrival Located On Star Lake In Formosa Gardens Of Kissimmee Florida. Complete Turn-key, Custom Built, Lavishly Furnished Home Including A Baby Grand Piano, Is Located Just A Few Short Minutes From Disney Theme Parks, Seaworld, Universal Studios And A Short Drive From The Orlando International Airport. For The Investor, This Home Has A Proven Track Record Of Bookings Even With A Global Pandemic Happening!! Currently There Are Just Under $170,000.00 In Bookings Starting 8/1/2020. No ...

7958 Sea Pearl Circle, KISSIMMEE

New Photo of Listing #S5028974

$1,200,000

  • 8 Beds
  • 8 Baths

  • 6,328 SqFt
  • 0.43 Acres

Single Family Residence

Formosa Gardens Unit 01

Completely Rebuilt To Demanding Specifications For The Latest In Design And Technical Innovations. Circular Paved Driveway Leading To Grand Entrance With Open Plan Foyer Similar To A Grand Hotel With Huge Freestanding Aquarium Visible On All Four Sides With Views Of Beautiful Tropical Fish. Large Dining Area Open To Family Room And Views Of Pool. Gourmet Kitchen Open To Large Family Room And Separate Dinette Again With Views Of Pool. Quartz Countertops And The Latest In Appliances. A Chef’s Delight. Large Well Equipped Games Rooms With Addit...

7985 Sea Pearl Circle, KISSIMMEE

New Photo of Listing #S5024669

$1,186,050

  • 7 Beds
  • 8 Baths
  • 1 Half

  • 7,907 SqFt
  • 0.33 Acres

Single Family Residence

Formosa Gardens Unit 01

*reduced Price* 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 Applianc...

535 Muirfield Loop, KISSIMMEE

New Photo of Listing #S5038113

$1,050,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 4,896 SqFt
  • 0.18 Acres

Single Family Residence

Reunion Resort

Major Price Improvement! Your Opportunity To Own The Ultimate In Vacation Homes Has Arrived. From The Active Reunion Membership To The Rooftop Sun Deck, This Home Oozes Luxury. This 5 Bedroom Home Is Currently Rented As A 6 Bedroom As They Utilized The Over-sized Second Living Room Off The Pool Deck To Maximize The Investment. An Open Floor Plan Brings Together The Gourmet Kitchen With Gas Appliances, Living Room, And 2 Dining Areas For A Cozy Group Experience. Right Off The Living Room, You Can Head Out To The Pool Deck Where You Will Find ...

2251 Yates Road, KISSIMMEE

New Photo of Listing #S5044377

$995,000

  • 4 Beds
  • 2 Baths

  • 2,048 SqFt
  • 13.15 Acres

Single Family Residence

Acreage & Unrec

Property Includes 2 Parcels; Parcel 1 Consists Of A Renovated 4/2 Ranch Style Home, Lots Of Storage Facilities, 2 Acre Lake, Plus A Ford Tractor With Bush Hog And Acreage Totaling 13.15 Acres. This Parcel Extends North Backing Up To Pioneer Village And To The East Shingle Creek. 2nd Parcel Is In Front Of House And Extends West 484' Wide Over To And Abuts Whispering Oaks Subdivision And Is .54 Of An Acre. Surrounding 40 Acre Parcel To The West Of Property Is Zoned Commercial And Multi Family. Owner Had Engineering Work Done In Years Pas...

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 January 22nd, 2021 at 8:27pm EST.