osceola county vacation homesOsceola County Vacation Homes

When you’re looking for Orlando vacation homes, one of the more popular areas to consider is Osceola County. This 1,500 square mile area serves as the south/central boundary of Central Florida. The county seat is Kissimmee, which is popular with tourists because of its proximity to the major theme parks, including Walt Disney World.

Osceola County was named for a Seminole warrior leader, who led several small, successful raids against the U.S. Army in the 1800’s. The county was formed in 1887 from portions of Orange and Brevard counties, and was a transportation hub in the late 19th century for riverboats and railroad. It later transformed into a cattle, sugar and lumber-based economy.

Check out the Osceola County Vacation Homes for Sale available below, or learn more about this popular area for Florida holiday communities.

Search Osceola County Real Estate Listings

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1164 Grand Traverse Pkwy, Reunion

Photo of Listing #S4844482

$2,599,000

  • 7 Beds
  • 7 Baths
  • 3 Half

  • 7,742 SqFt
  • 0.32 Acres

Single Family / Villa

Reunion West Village 03a

Pre-construction. To Be Built By Landmark Custom Builder, One Of Central Florida's Premier Master Builders. This Amazing Custom Home Of Distinction Located On One Of The Largest Lots In Beautiful Reunion Resort And Club Will Have The Exceptional Detail & Superior Craftsmanship That Sets Landmark Apart. Ideal For Personal Or Rental Aspirations. Backing To Conservation W/ Seven 1st Floor En-suite Bedrooms Including 2 Large Masters W/grand Bathrooms & Walk-in Closets. Two Of The Secondary Bedrooms Are Separated By A Hidden Themed Playroom. Invi...

901 Desert Mountain Ct, Reunion

Photo of Listing #O5484556

$2,400,000

  • 10 Beds
  • 11 Baths
  • 1 Half

  • 7,993 SqFt
  • 0.25 Acres

Single Family / Villa

Reunion West Village 03a

Under Construction. Stunning 10 Bedroom, 11 Full Bathroom And One Half Bath Custom Build Vacation Home Investment Property By Legacy Custom Homes. This Unique Home Is The Ideal Vacation Rental Investment Home With Oversized Kitchen, Dining Area, Great Room, Movie Theater, Game Room And Two Master Suits. Outdoor Living Is A Pronounced Feature Of This Home With Large Covered Lanai And A Fully Equipped Summer Kitchen. A Fantastic Heated Pool And Spa Is Included. The Split Conservation / Golf Rear View Offers The Best In Both Privacy And Beauty...

331 Muirfield Loop, Reunion

Photo of Listing #O5500221

$1,800,000

  • 10 Beds
  • 11 Baths
  • 3 Half

  • 7,966 SqFt
  • 0.20 Acres

Single Family / Villa

Reunion West Vlgs North

This 10 Bedroom, 11 Bathroom Three Story Revenue Generating Investment Property Offers Its New Owner Immediate Inclusion Into The League Of The Handful Of Double Digit Bedroom Count Top Of The Line Vacation Home Investment Properties In Reunion. This Stunning Home Has Everything Needed To Produce Significant Revenue Flow For Many Seasons To Come. Custom Designed And Purpose Built As A Vacation Home, This Exceptional Property Has An Abundance Of Well-designed Rooms And Professionally Decorated To Provide Maximum Impact For High Ticket Accommo...

2713 Formosa Blvd, Kissimmee

Photo of Listing #S4833802

$1,725,000

  • 9 Beds
  • 10 Baths
  • 1 Half

  • 7,600 SqFt
  • 0.33 Acres

Single Family / Villa

Formosa Gardens Unit 01

This Stunning Luxury 9 Bedroom Villa Is One Of The Largest And One Of The Most Exclusive Vacation Villas In Formosa Gardens, With Over 9,500 Sq Ft. Of Living Area Featuring A Movie Room, Sports Room With Gymnasium And Pool Table, & 1500 Game Arcade Machine. There Is A Grand Piano, 2 Staircases, 120 Feet Of Balconies, Infinity Pool And Hot Tub Overlooking A Beautiful Lake Front. This Exquisite Villa Occupies A Prime Location In The Popular Formosa Gardens Estates, Directly On The Lakefront With A South Facing Pool. It Is Undoubtedly One Of T...

415 Muirfield Loop, Reunion

Photo of Listing #O5500224

$1,680,000

  • 8 Beds
  • 8 Baths
  • 3 Half

  • 6,832 SqFt
  • 0.21 Acres

Single Family / Villa

Reunion West Vlgs North

Located On One Of Reunions Most Exclusive Streets - Muirfield Loop, This Fabulous 8 Bedroom 8 Bathroom 7,800 Sq Ft Jack Nicklaus Golf Course Vacation Home Is Ready To Continue Its Successful Rental Revenue Flow For A New Owner. Custom Designed And Professionally Decorated This Home Has Everything An Owner Or Guest Could Wish For. Extravagant Finishes, Copious Room Space, Movie Theater, Games Room And Excellent Our Door Living Complete With Large Pool And Deck Space Make This Home A Prime Choice For A Buyer Eager To Get Started With A Vacatio...

395 Muirfield Loop, Reunion

Photo of Listing #O5500225

$1,650,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 5,563 SqFt
  • 0.21 Acres

Single Family / Villa

Reunion West Vlgs North

Used By Its Current Owner Only As A Second Home This 5 Bedroom, 5 Bathroom Delight Offers A Buyer The Unique Opportunity To Own One Of The Most Charming Homes On The Executive Section Of Reunion. Located On The Prestigious Muirfield 14th Hole, The Home Offers A Grand View Of The Golf Course And Offers Privacy And Ambiance In Abundance. Within, The Finishes Are Exceptional With Fine Stone, Wood And Textures Throughout. Nice Open Plan Design And Oversized Bedrooms Makes It Feel Larger Than The 5,563 Sqft It Provides. Full Length Rear Back Balc...

7831 Palmilla Ct, Reunion

New Photo of Listing #S4848166

$1,400,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 4,751 SqFt
  • 0.36 Acres

Single Family / Villa

Reunion West Vlgs North

This 5-bedroom Estate Vacation Home Features Custom Architecture And Gorgeous Golf Course And Balcony Views, Providing A Beautiful Backdrop For A Dream Florida Vacation! Accommodations Include 4 Master Bedrooms And Harry Potter Themed Room, All With Lcd Tvs. Outside There Is A Pool Beautifully Designed With Italian Tiles And A Spillover Spa. There Is A Sitting Area With A Gas Fire Pit And A Summer Kitchen For Entertaining. The Home Also Features A Living Area With A 50' Plasma Tv And Blu-ray Player, A Gourmet Kitchen And Formal Dining Area. ...

8192 Valhalla Ter, Reunion

Price
Reduced
Photo of Listing #O5491039

$1,325,000

  • 8 Beds
  • 8 Baths
  • 2 Half

  • 5,942 SqFt
  • 0.18 Acres

Single Family / Villa

Reunion West Village 3b

No Need To Wait To Build. This 8 Bedroom 8 And Two 1/2 Bath Beauty Awaits Your Arrival. The Luxurious Retreat Reflects The Magical Merging Of Inspiration And Architecture. Sprawling Entertaining Spaces Flow Outside To The Outdoor Lanai And Stunning Pool And Private Back. There Is A Dedicated Game Room As Well As A Theater Upstairs. Finished In Fine Stone Textures And Fittings Throughout, This Home Has An Overall Feel Of Elegance Yet Still Is Robust Within The Design Elements That It Can Easily Accomplish A High Traffic Profile If Its New ...

N/A, Reunion

Price
Reduced
Photo of Listing #S4842360

$1,300,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 4,726 SqFt
  • 0.19 Acres

Single Family / Villa

This Is Not Your Average Vacation Home. Every Step Of Interior Décor Has Been Designed With Your Comfort In Mind. Step Into This Luxurious This Home And Allow Your Dreams To Come True.from The Moment You Step Into The Magnificent Entranceway Your Eyes Are Pulled In Many Different Directions From The Formal Vaulted Ceilings With Cascading Modern Chandelier, Your Eyes Are Pulled Past The Large Formal Dining Table With Gas Lit Central Feature Fireplace To The Complete Wall Of Patio Windows. The Windows All Open To Complete The Indoor/outdoor ...

1215 Radiant St, Reunion

Photo of Listing #O5485196

$1,250,000

  • 7 Beds
  • 6 Baths
  • 1 Half

  • 5,226 SqFt
  • 0.22 Acres

Single Family / Villa

Reunion Ph 01 Prcl 01 Un...

This Gorgeous, Custom Vacation Home, 7 Bedroom, 6 Bathroom, 5200+ Sq.ft. Home Is Located In Desirable Homestead Closest To The Reunion Grande And Walking Distance To The Reunion Spa. This Home Is One Of The Only 7 Bedroom Home Available In Reunion Resort. The Over-sized Lot Is Located On The 8th Hole Of The Tom Watson Golf Course With A Beautiful View Of Open Green And Preserve With Side Yard For Extra Fun. Features Include Two-story Grand Entry, Three-story Dining Hall, Home Theater, Game Room, Four King Master Bedroom Suites With Private B...

1200 Wynstone Way, Reunion

Price
Reduced
Photo of Listing #S4841038

$1,250,000

  • 7 Beds
  • 6 Baths

  • 3,975 SqFt
  • 0.30 Acres

Single Family / Villa

Reunion West Village 03b

This Exquisite Property Is One Of The Most Private In The Whole Of Reunion Resort. It Has 7 Beautiful Bedrooms, & 6 Bathrooms. This Custom Home Provides Luxury Upscale Living Accommodation With Its Completely Private, Enclosed Pool Area, With Garden And Lake Views & Summer Kitchen. It Has An Atmospheric Theatre Room That Has 10 Reeling Seats & A Games Room With Pool Table & Foosball. As You Pull Up Onto Your Private Driveway, You Will Be Met By The Impressive Portico Entrance. The Double Front Doors Open Up Onto A Majestic Entrance Hall Floo...

454 Muirfield Loop, Reunion

Photo of Listing #O5509533

$1,200,000

  • 6 Beds
  • 6 Baths
  • 1 Half

  • 5,017 SqFt
  • 0.21 Acres

Single Family / Villa

Reunion West Vlgs North

One Of The Largest Pools In All Of Reunion! The Outdoor Space Is Amazing Overlooking The Jack Nicklaus Signature Golf Course And Conservation. Tongue And Groove Covered Outdoor Kitchen Area Features: Gas Grill, Refrigerator, Sink, Bathroom With Shower. The Entire Pool Deck Is Rough Covered Travertine With Lots Of Space To Enjoy The Florida Sun! The Layout Of This 6 Bedroom / 6.5 Bathrooms Custom Estate Home Is What Makes This Home So Special: Large Spacious Rooms With Tall Ceilings, Travertine Flooring, Master Bedrooms Up And Down, 3 Ba...

Living in Osceola County

The area became well-known as a tourist destination after Walt Disney World opened in the 1970s. Today, there are plenty of attractions to keep visitors amused, such as Old Town which features a family fun track, arcade, shops, restaurants, and gift shops.

One of the appeals of owning a second home in Osceola County is that the area is home to the Kissimmee Chain-of-Lakes, which includes some of Florida’s largest and finest fishing and recreational attractions like Lake Tohopekaliga. World renowned for bass fishing, Lake Toho, as it’s known to locals, is also a popular place to take an airboat ride to view the Florida wilderness and headwaters that feed the Everglades.

Osceola County Real Estate Market

Vacation home buyers have a large choice of home and community types to choose from in Osceola County. There are gated communities for extra privacy, as well as resort and waterfront communities. Vacation homes available for sale include luxurious single family homes and villas, condos and townhouses.

For example, you’ll find beautiful Kissimmee vacation homes for sale at the Reunion Resort. This amazing resort is the only one in the world that features three signature golf courses designed by the sport’s greatest legends: Jack Nicklaus, Arnold Palmer and Tom Watson. The resort also includes its own water park with a lazy river and twisting water slides, as well as additional swimming pools, Jacuzzis and poolside dining.

If you have any questions about the homes for sale in Osceola County, contact a Team Donovan agent today at 407-705-2616. We look forward to helping you select your ideal Orlando vacation home.

Browse Osceola County Holiday Home Communities:

Are you interested in purchasing vacation property in Osceola County? We encourage you to contact the Donovan Team online or give us a call at 407-705-2616. We'd be thrilled to help you find yourself a beautiful Orlando vacation home near Disney World!

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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.

Listing information last updated on June 26th, 2017 at 9:51am EDT.