Orlando Vacation Homes for Sale

Most people only know Orlando, Florida as the Theme Park Capital of the World. But The City Beautiful, as it's also known as, offers much more including affordable living, a vibrant arts scene, plentiful shopping, spas, golf, dining, outdoor adventures and nightlife for residents and visitors to enjoy. The wonderful Orlando vacation homes for sale place residents at the center of it all!

For those wishing to buy a second home to use as a vacation home or for investment income, Orlando is an excellent choice. Sales taxes are low, and there are no state income taxes. Orlando is also home to the University of Central Florida, which is the largest university in the United States by undergraduate enrollment. 

Check out the available Orlando vacation real estate listings below, or continue reading to learn more about the many wonderful holiday communities found in the city!

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2,178 Properties Found. Showing Page 1 of 182
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9291 Point Cypress Drive, ORLANDO

New Photo of Listing #O5965014

$25,000,000

  • 12 Beds
  • 13 Baths
  • 2 Half

  • 14,706 SqFt
  • 2.40 Acres

Single Family Residence

Cypress Point Ph 02

Welcome To Entrelagos, An Extraordinary Estate Located On A Private Peninsula Between Lake Sheen And Lake Tibet On The Prestigious Butler Chain Of Lakes In Windermere Florida. From Its Beginning, Every Detail Of This Three-story, 14,706 Square Foot Mansion Was Given Exceptional Attention. Taking Almost Ten Years And $8m To Complete, Most Of The Interior Features Were Handcrafted By Filipino Artisans And Shipped To The Us. Massive Wooden Columns And Interior Doors Are Hand Carved And Painted Works Of Art. The Main Entry Door Was Cust...

9200 Bentley Park Circle, ORLANDO

New Photo of Listing #L4930944

$15,000,000

  • 7 Beds
  • 8 Baths
  • 4 Half

  • 20,690 SqFt
  • 1.83 Acres

Single Family Residence

Bentley Park 2nd Rep

This Incredible Estate Known As 'bentley Hall' Sits On A Massive 2 Acre Lot Located In The Heart Of Central Florida Just Minutes From Walt Disney World And Universal! World Class Resorts, Shopping, Golf And Restaurants Are Abundant In This Area As Well As All Of The Theme Parks, However As Soon As You Drive Through The 24 Hour Monitored Security Gate You Will Feel Like You Have Entered Your Own Private Oasis. It Is Located Within The Sought After Bentley Park Community Within Bay Hill In The Dr Phillips Area. This Home Boasts Over 20,000 Sqf...

10217 Symphony Grove Drive, ORLANDO

New Photo of Listing #O6048451

$7,800,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 5,241 SqFt
  • 0.32 Acres

Single Family Residence

Golden Oak Phase 5

Imagine A Fairytale Residence Where Dreams Really Come True. A Masterpiece In Every Sense Of The Word; A Home Elegantly Crafted With The Finest Hand-selected Materials On Earth To Showcase The Enchantment Of Disney, Located Within The Private Guarded Gates Of The Most Magical Address In The World. Presenting Golden Oak At Walt Disney World® Resort And An Exquisitely Appointed, Masterfully Executed, Homage Of Dream Making Technology, Design, And Art. This Symphony Grove Storybook Estate Residence With Private Guest House Was Thoughtfully Conc...

10203 Atterbury Court, ORLANDO

New Photo of Listing #O6024532

$6,995,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 10,222 SqFt
  • 1.53 Acres

Single Family Residence

Lake Nona Estates

Set Along The Front Nine Of Lake Nona Golf & Country Club’s Renowned Championship Golf Course With Magnificent Panoramas Over Multiple Golf Holes And Water, This Exquisite Golf Course Estate Has Been Fully Updated With Gorgeous Interiors Reflective Of Today’s Fresh, Modern Style. One Of The Largest Of Lake Nona’s Properties Set On Two Home Sites Totaling More Than 1.5 Acres, The Estate Offers A Sprawling Floor Plan Of More Than 10,000 Square Feet With Superb Living Spaces In A Beautiful Setting. Centrally Located Within The Gates, The Vast...

10330 Wittenberg Way, ORLANDO

New Photo of Listing #O6029473

$4,999,990

  • 6 Beds
  • 7 Baths
  • 1 Half

  • 9,272 SqFt
  • 0.66 Acres

Single Family Residence

Moss Park Reserve

Gated, Lakefront, Pool In Moss Park Reserve! Very Energy Efficient Home Including Construction With Icf Block. It’s Rare To Find A Home That Stops You In Your Tracks. One That Is Jaw-dropping, Breathtaking, And Completely Amazing.this Home Is Sure To Exceed Even Your Wildest Dreams. While The Home Is The Property’s Crown Jewel, The Grounds Create Awe. A Brick Paver Circular Driveway Winds Up To The Home With Split 2-car Garages To Store All Your Cars, Boats And Water Toys. Positioned On A .66 Home Site And Surrounded By Lush, Mature Landscap...

9830 Sloane Street, ORLANDO

New Photo of Listing #O6059151

$4,200,000

  • 4 Beds
  • 4 Baths
  • 2 Half

  • 6,026 SqFt
  • 1.26 Acres

Single Family Residence

Lake Nona

Welcome To The Previous “street Of Dreams” Within Lake Nona Golf & Country Club Where There Are Only 7 Homes, Each On Over 1 Acre & All With Pond Views In The Back & Conservation Views In The Front. Privacy, Space & Beautiful Nature At It’s Finest For You To Enjoy Spectacular Sunsets From Your Tremendous Outdoor Living Areas Overlooking The Glistening Pond. Prepare To Be Immediately Impressed When You Walk Through The Double Entry Front Doors & See Straight Through To The Gorgeous Oasis With The Lanai, Pool, Spa & Pond. This Gorgeous 1-story...

10300 Pocket Lane, ORLANDO

New Photo of Listing #O6038599

$4,199,000

  • 5 Beds
  • 3 Baths
  • 2 Half

  • 6,446 SqFt
  • 2.64 Acres

Single Family Residence

Willis R Mungers Land Sub

One Or More Photo(s) Has Been Virtually Staged. Home Consists Of 4 Living Areas Of 6446 Sq Ft Surrounding A Central Enclosed 6619 Sq Ft Enclosed Spacious Lanai With Pool, Spa And Used For Recreation Giving 13000 Sq Ft Of Living Space. Four Of The Bedrooms Including The Stunning Master Bedroom Have Access To A Porch Overlooking The Canal. The Kitchen, Living Room And Study Have A Breathtaking View Of Pocket Lake. The House Is On The Butler Chain Of Lakes And 30 Feet From The Water. The Fish-pocket Canal Runs Through The Property, And There Is...

8527 Lake Nona Shore Drive, ORLANDO

New Photo of Listing #O6056559

$3,975,000

  • 5 Beds
  • 6 Baths
  • 1 Half

  • 6,174 SqFt
  • 0.35 Acres

Single Family Residence

Lake Nona Estates

Under Construction. By Barcellona Homes, This Two-story Contemporary Residence Creates An Aesthetic That Is Conducive To Both Grand Entertaining And Small Gatherings. With An Exterior Made Of Stone Wall And Wood Tile, This Home Includes Five Bedrooms, Six Full And One-half Bathrooms Within 6,174 Square Feet. Wall-to-wall Sliding Glass Doors Captivate Your Attention From The Moment You Enter The Foyer, Providing Views Through The Great Room Out To The Incredible Outdoor Living Area. The Open Floor Plan Seamlessly Blends The Interior Living Sp...

601 East Jackson Street, ORLANDO

New Photo of Listing #O6039481

$3,500,000

  • 5 Beds
  • 3 Baths

  • 5,000 SqFt
  • 0.50 Acres

Single Family Residence

Wilmotts Plan

Prime Residential/mixed-use Development Opportunity In Downtown Orlando's Most Desired Neighborhood. 3 Blocks From Central Business District In The Trendy And Upscale South Eola/thornton Park Neighborhood Of Downtown Orlando. Walking Distance To Cbd, Lake Eola Park And Thornton Park. A Total Of Four Lots At The End Of The Block Facing South Eola Drive. South Side Of Site Is Across From City Park And Dog Run. Great Established And New Development In This High Average Income And Highly Desirable Area Of Downtown. Catty-corner From The New $88m...

8040 Firenze Boulevard, ORLANDO

New Photo of Listing #S5070919

$3,500,000

  • 5 Beds
  • 4 Baths
  • 1 Half

  • 6,314 SqFt
  • 0.52 Acres

Single Family Residence

Vizcaya Ph 01 45/29

Celebrity Home! The “casa Della Musica” Of A Member Of The Most Successful Boy Band Group For Over 14 Years. One Of A Kind Lakefront Home On Vizcaya Dr Phillips – Paradise Found! Enter The Property Through Automatic Gates, To Your Choice Of 5 Garages, All With Direct Entry To The House – This Property Is All About Lakefront Living And Ultimate Privacy, Designed To Emerse You In The Panoramic Lakefront Spectacle, With Some Of The Most Impressive Views Orlando And Nightly Views Of Dramatic Sunsets And Fireworks From Most Areas Of The Ho...

8575 Lake Nona Shore Drive, ORLANDO

New Photo of Listing #O6054276

$3,350,000

  • 4 Beds
  • 4 Baths
  • 1 Half

  • 4,265 SqFt
  • 0.35 Acres

Single Family Residence

Lake Nona Estates

Luxury, Form And High Function Are The Hallmarks Of This One Story 4,300 Sf Contemporary Residence Tucked Away From The Main Thoroughfare Yet Minutes From A World Class Golf Course And Amenities. A Lush Backyard Oasis Frames A Gorgeous Pool And Spa That Appears To Cascade Seamlessly Into A Pond. Retractable Screens, Shaded Sitting Areas Throughout The Expansive Deck, Tv Stations, And A Sun Shelf Will Have You Fully Embracing The Fl Lifestyle. A Summer Kitchen With A Bbq Station, Side Burner, Sink, Fridge And Dishwasher Make Al Fresco Dini...

9864 Covent Garden Drive, ORLANDO

New Photo of Listing #O6045180

$3,300,000

  • 5 Beds
  • 4 Baths
  • 3 Half

  • 5,760 SqFt
  • 0.33 Acres

Single Family Residence

Lake Nona Estates

Set Along The Front Nine Of Lake Nona Golf & Country Club’s Renowned Championship Golf Course, This Exquisite Courtyard-style Home Offers Breathtaking Views Of Multiple Golf Holes And Water. Built By Leading Central Florida Custom Home Builder Cahill Homes, The Estate Spans 5,760 Square Feet Across Two Levels And Offers 5 Bedrooms, 4 Full And 3 Half Baths. Beyond The Beautiful Turret Entry, A Welcoming Courtyard Features A Sparkling Pool Surrounded By A Private Deck With Summer Kitchen And Guest Cabana. The Interior Features Are A Stunnin...

The Orlando Community

Orlando’s history dates back to the 1800s, when the U.S. Army established an outpost south of the current downtown during the Second Seminole War. The town later became the county seat of the new Orange County in 1856, and enjoyed status as the hub of the state’s citrus industry in the late 1800s.

Tourism became the driving force in Orlando’s economy after Walt Disney World opened in 1971. Since then, Universal Orlando, Sea World, Gatorland and other attractions have successfully attracted millions of visitors from around the globe. Health care is also a growing economic driver, with the addition of the University of Central Florida medical school and the hospitals, research facilities and other establishments located in the new Lake Nona Medical City area. 

Orlando Real Estate Market 

The historic core of “Old Orlando” lies along Church Street, between Orange and Garland Avenues downtown. This historic district includes the Lake Eola Heights and Thornton Park neighborhoods, which feature some of the oldest homes in the city. 

There are also plenty of newer housing communities in Orlando, offering a range of options such as single family homes, townhomes, condos and condo/hotels. Short-term rentals are only allowed in condos and townhomes, with most being offered in resort-style communities located near Disney World, such as Floridays Orlando, Lake Buena Vista and Blue Heron Beach.

Browse Orlando Holiday Home Communities:

If you’d like more information about purchasing an Olando vacation home, contact a Team Donovan agent at 407-704-2616 or or visit us online.

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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 September 24th, 2022 at 5:34pm EDT.