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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1,047 Properties Found. Showing Page 1 of 88
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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...

500 Muirfield Loop, Reunion

Price
Reduced
Photo of Listing #O5443843

$2,565,000

  • 9 Beds
  • 9 Baths
  • 3 Half

  • 9,998 SqFt
  • 0.53 Acres

Single Family / Villa

Reunion West Vlgs North

This Trend Setting Investment Property Has Been One Of Reunions Most Successful Luxury Executive Vacation Homes Since Is Completion In 2012. Designed And Built To Accommodate Guests Seeking The Ultimate In Vacation Home Luxury Accommodation In The Orlando Area. Built On A Double Private Preserve Lot On Sought After Muirfield Loop And Part Of The Jack Nicklaus Designed Signature Golf Course, This Magnificent Nine Bed, Nine And Three Half Bath Masterpiece Is Designed Specifically To Facilitate The Ultimate Experience. The Home Features Many...

712 Desert Mountain Ct, Reunion

Photo of Listing #S4849657

$2,495,000

  • 12 Beds
  • 12 Baths
  • 2 Half

  • 8,879 SqFt
  • 0.22 Acres

Single Family / Villa

Reunion West Village 03a

Amazing 12 Bedroom, 15 Bathroom Reunion Rental With Huge 60 Foot Pool And Spa, Games Room, Cinema, Gymnasium, Private Pool, Spa, Sunken Pool Bar, Pool Sun Shelf, Water Slide, Golf Putting Green Plus Spectacular Golf Views.

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...

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

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. ...

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 ...

7809 Palmilla Ct, Reunion

Price
Reduced
Photo of Listing #S4848273

$1,285,000

  • 4 Beds
  • 3 Baths
  • 1 Half

  • 4,019 SqFt
  • 0.27 Acres

Single Family / Villa

Reunion West Vlgs North

Old-world Mediterranean Elegance Is Felt As Soon As You Enter The Front Door With Beautiful Rot Iron Spiral Staircase, Travertine Flooring And Hand Scratched Woodwork Throughout. Custom Detail Of The Home With Large Open Archways, Luxury Chef's Kitchen With Granite Countertops, Superior Fixtures Even A 6 Burner Gas Stove With Stainless Steele Appliances. There Is A Unique Curved Formal Dining Area That Will Make You Feel Like Your Dining In A Castle And A Formal Living Room With Gas Fireplace That Will Let You Spend Some Quite Time With Your...

1110 Watson Ct, Reunion

Photo of Listing #S4849232

$1,275,900

  • 7 Beds
  • 7 Baths
  • 1 Half

  • 5,898 SqFt
  • 0.16 Acres

Single Family / Villa

Reunion Ph 1

Available To View Today...pure Luxury In The Heart Of Reunion Resort, With One Of The Largest Custom Built Estate Homes Available Boasting Almost 6,000 Sq Ft Under Air. The 7 Bedroom Home Also Comes With 7 ½ Fully Upgraded Bathrooms Some Even Include Deep European Soaking Tubs, Walk-in Double Head Showers And Custom Tiling Throughout. The Chef Inspired Kitchen Includes Large Island, Double Wide Refrigerator, Large Open Dining Area And Spacious Living Room With Exposed Wood Beams And Built In Modern Fireplace. Your Guest Will Love The Upsta...

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...

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 August 18th, 2017 at 2:18am EDT.