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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4441 Anderson Rd, Kissimmee

Photo of Listing #S5026748


  • 4 Beds
  • 4 Baths

  • 1,608 SqFt
  • 12.34 Acres

Single Family Residence

Acreage & Unrec

One Or More Photo(s) Has Been Virtually Staged. Beautiful Property Right Off 17-92 And Ham Brown In The Fast-growing Kissimmee Area! With Just Under 13 Acres, This Property Contains Two Homes (one Sfr With Pool And One Doublewide Mobile Home), Three Barns/outbuildings, Rv Parking, Retention Pond And More! With Ham Brown Frontage, The Possibilities Are Endless! The Main Home Contains 3 Bedrooms, 2 Baths, 1,608sf, And An In-ground Pool. The Second Home Contains 4 Bedrooms, 3 Full Baths, And Boasts 2,340 Sf. With Fencing, Workshops, Cattle Corr...

4445 Austin Rd, Kissimmee

Photo of Listing #S5026767


  • 3 Beds
  • 2 Baths

  • 1,560 SqFt
  • 8.02 Acres

Single Family Residence

Acreage & Unrec

Come View This Great Property Located Just Off 17-92 And Ham Brown Rd. With Ham Brown Access, This Lot Contains Just Over 8 Acres Of Serenity. The Property Contains A Block, Sfr With 3 Bedrooms, And 2 Baths, As Well As A Separate Single Wide Mobile Home Containing 1,064sf. Zoned For Horses And Other Agricultural Options, With An Additional Barn/workshop, This Property Is A Must-see!

4421 Reaves Rd, Kissimmee

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...

21 E Lakeshore Blvd, Kissimmee

Photo of Listing #O5828006


  • 6 Beds
  • 7 Baths
  • 2 Half

  • 9,328 SqFt
  • 3.49 Acres

Single Family Residence

Florida Fruit Belt Sales Co

Back On Market! Buyer Failed To Close. Huge Price Drop! Well Below Appraisal Value! Welcome To Your Private, Gated, Lakefront Mansion Residing On Nearly 4 Acres Of Fenced In Land, With Your Own Tennis/basketball Court And Private Dock To Lake East Toho. This Magnificent Estate Is Truly One Of A Kind And Definitely Makes A Statement! Enjoy Entering This Compound Through Your Own Private Gate, Winding Down Your Long, Circular Paver Driveway Surrounded By Huge Palm Trees And Lush Landscaping. This 9,328 Sf Estate Boasts 6 Bedrooms, 7 Full Baths...

2713 Formosa Blvd, Kissimmee

Photo of Listing #O5795273


  • 9 Beds
  • 10 Baths
  • 1 Half

  • 8,198 SqFt
  • 0.33 Acres

Single Family Residence

Formosa Gardens Unit 01

This Turn-key Estate 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 Floors Where The Home's Baby Grand Piano Sounds The Best. As You Reach The Top Of Its Sweeping Staircase Where Many Wedding Picture Have Been Taken You'll Notice New Plank Fl...

9054 Paolos Place, Kissimmee

Photo of Listing #O5794605


  • 5 Beds
  • 5 Baths
  • 2 Half

  • 6,312 SqFt
  • 1.64 Acres

Single Family Residence

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...

7937 Sea Pearl Cir, Kissimmee

Photo of Listing #S5024681


  • 7 Beds
  • 8 Baths
  • 1 Half

  • 9,128 SqFt
  • 0.42 Acres

Single Family Residence

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...

1881 Pleasant Hill Rd, Kissimmee

Photo of Listing #P4909812


  • 6 Beds
  • 6 Baths
  • 2 Half

  • 9,889 SqFt
  • 11.11 Acres

Single Family Residence

Forest Unit 01

This Unique Custom Built And Designed Home Is A Vintage Treasure! It’s Been Said That This One-of-a-kind Original Mimics The Ideas Of Disney's Frontierland. Within This 11 +/- Acre Estate You Will Find A Lagoon With Three Islands, Canoe Trails, And A Zipline Over Two Waterways. The Beautiful Lodge Style Home With It's Rustic And Inviting Charm Will Make You Will Feel Right At Home As You Enter. The Interior Displays Massive Stone Fireplaces And Beautiful Cedar And Pine Ceilings. The Kitchen Was Built So A Large Family Or Group Could Gather I...

3080 Parrot Head Pl, Kissimmee

Photo of Listing #O5862664


  • 8 Beds
  • 9 Baths
  • 2 Half

  • 4,518 SqFt
  • 0.08 Acres

Single Family Residence

Rolling Oaks Ph 5

One Of A Kind Opportunity To Own In Margaritaville Resort On The Best Row In Margaritaville!!! There Are Only A Handful On Homes On The Private Lake And They Do Not Come On The Market Very Often. One Of The Largest Floor Plans In The Community That Has The Shortest Walking Distance To The Many Resort Amenities. Price Includes Margaritaville Approved Ethan Allen "in Paradise" Furniture Package Valued At $105,000 (plus 7.5% Sales Tax), Plus An Additional $8,000 For Pool Table, $2,000 For Arcade Game And $2500 For Upgraded Custom Crown Moldin...

7985 Sea Pearl Cir, Kissimmee

Photo of Listing #S5024669


  • 7 Beds
  • 8 Baths
  • 1 Half

  • 7,907 SqFt
  • 0.33 Acres

Single Family Residence

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...

8450 Natures Hammock Trail Trl, Kissimmee

Photo of Listing #O5863334


  • 9 Beds
  • 7 Baths

  • 5,600 SqFt
  • 5.01 Acres

Single Family Residence


Under Construction. Welcome To A One Of A Kind Retreat Center. Designed Ideally For A Large Family, Corporate Gatherings, Or Potentially A Bed And Breakfast (note A Bed And Breakfast Must Have Host On The Property). Current Zoning Is Agricultural Which Allows Animals. Future Zoning Is Low Density Residential Which Would Allow Buyers To Add More Buildings. One Of The Four Buildings Is Complete, With The Rest Coming Soon. Price Is As/is. Completed Price Is 1,495,000.

7958 Sea Pearl Cir, Kissimmee

Photo of Listing #S5028974


  • 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...

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 June 1st, 2020 at 4:00am EDT.