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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771 Properties Found. Showing Page 1 of 65
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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...

9236 Bay Point Drive, ORLANDO

New Photo of Listing #O5854037

$6,675,000

  • 6 Beds
  • 8 Baths
  • 2 Half

  • 9,764 SqFt
  • 0.73 Acres

Single Family Residence

Bay Point/ Bay Hill

Constructed To Seamlessly Blend The Best Of Old-world Design And Contemporary Elegance, This Brand New Lakefront Home Exudes An Air Of Sophistication Through Perfectly Placed Mixed Materials, Panoramic Views Of Lake Tibet, And An Open Floor Plan. Located Within Gated Bay Point, Just Steps From Famed Bay Hill Golf Course, The Home Is Sure To Inspire Awe As You Make Your Way Up The Stone Paver Driveway And Through The Custom Glass Entry. Polished Stone Floors, Luxurious Grand Staircase, Custom Light Fixtures, And A Full-size Wine Cellar Tucked...

13337 Kirby Smith Road, ORLANDO

New Photo of Listing #O5975375

$6,200,000

  • 5 Beds
  • 7 Baths
  • 1 Half

  • 9,609 SqFt
  • 4.22 Acres

Single Family Residence

N/a

Live The Dream On Lake Hart. Minutes Away From Disney World's Future 60-acre Campus, Lake Nona Medical City, Orlando International Airport, Golf Courses, Great Schools And More. This Private, One-of-a-kind Estate Has 300 Ft Of Waterfront On 4.22 Pristine Acres And Feels Like You Are Living In A Five-star Resort. Designed To Maximize Views From Every Room, This Home Will Exceed All Of Your Expectations. Offering 9,609 Interior Square Feet And 15,573 Total Square Feet With Outdoor Living, The Home Boasts 5 Bedrooms, 7.5 Baths With Custom Finis...

9186 Bay Point Drive, ORLANDO

New Photo of Listing #O5993236

$3,990,000

  • 4 Beds
  • 4 Baths
  • 1 Half

  • 4,167 SqFt
  • 0.44 Acres

Single Family Residence

Bay Point

Stunning One Story Home Perfectly Positioned Along The Shores Of Lake Tibet On The Butler Chain Of Lakes. This Exquisite Residence Is Located Within Gated Bay Point, Just Steps From Famed Bay Hill Golf And Country Club. As You Step Through The Front Doors, You're Immediately Greeted By Bright Open Spaces And High Ceilings With Panoramic Views Of Lake Tibet And Pool. The Chef In The Family Will Fall In Love With The Modern Kitchen Featuring Striking Quartz Countertops, Custom Cabinetry And Top-of-the-line Wolf Stainless Steel Appliances. The...

5378 Bay Side Drive, ORLANDO

New Photo of Listing #O5986538

$3,950,000

  • 4 Beds
  • 4 Baths
  • 2 Half

  • 5,224 SqFt
  • 2.11 Acres

Single Family Residence

North Bay Sec 04-a 48 142

The Lifestyle You Desire Is Waiting For You In This Private European Waterfront Property. Featuring Picturesque Water Views In The Coveted Bay Hill Area, This Home Has An Open Floor Plan Flooded With Natural Light And Walls Of Windows Providing Stunning Views Of The Lake And Custom Infinity Pool Overlooking The Chain Of Lakes. This Well-appointed 5,224 Square Foot Home Features Four Bedrooms, An Executive Office, Four Full Baths And Two Half Baths. The Chef’s Kitchen Enhances The Interior, Featuring Quartz Countertops, La Cornue Range, Doubl...

601 East Jackson Street, ORLANDO

New Photo of Listing #O5959225

$3,840,000

  • 2 Beds
  • 1 Baths

  • 5,000 SqFt
  • 0.50 Acres

Single Family Residence

Wilmotts Plan

Prime Mixed-use Development Opportunity In The Trendy And Upscale South Eola Neighborhood Of Downtown Orlando. Four Lots Comprising The End Of A City Block. Walking Distance To Central Business District, Lake Eola Park And Thornton Park. Total Of Four Lots. South Side Of Site Is Across From City Park. Great Established And New Development In This High Average Income And Highly Desirable Area Of Downtown. Catty-corner From The Newly Finished, 12-story, 364 Unit Camden Lake Eola (luxe Rentals). Great Walkability, Close To Publix, Shops, Dining...

9202 Cromwell Park Place, ORLANDO

New Photo of Listing #O5977860

$3,500,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 6,662 SqFt
  • 0.86 Acres

Single Family Residence

Lake Nona Estates

Situated On A Private Cul-de-sac Within The Renowned Lake Nona Golf & Country Club, This Exquisite Custom Estate Blends Exceptional Finishes With Gorgeous Living Spaces To Create A Beautiful Romanesque Masterpiece. Built By Leading Custom Home Builder Pellegrini Homes, The Estate Is Positioned On A Corner Home Site In Proximity To The Club And Amenities. Beyond The Circular, Paver Driveway And Lovely Courtyard Garden, An Arched, Wooden Entry Door Reveals A Chic Foyer With An Elegant Chandelier, Spiral Staircase, A Beautiful Gallery With Gor...

9131 Southern Breeze Drive, ORLANDO

New Photo of Listing #O5962884

$3,395,000

  • 7 Beds
  • 6 Baths
  • 2 Half

  • 8,328 SqFt
  • 4.22 Acres

Single Family Residence

Estates At Phillips Land...

This Majestic Lakefront Estate On Big Sand Lake Offers The Life Style You Want. A True Custom Home On A Beautiful Water Front Lot With Tons Of Special Features And Natural Lightings That Give Warm And Luxury Feeling To The House. The Iron Front Door Leads To The High Ceiling Foyer And Living Room, Stone Columns, Arches And Custom Made Stunning Chandeliers Whole Thru Out The House. The First Floor Includes An Elegant Office, A Master Suite With Morning Bar, Generous Sitting Area With A Fire Place, His And Her Dressing Rooms, Private Patio ...

19405 Lake Pickett Road, ORLANDO

New Photo of Listing #O5866029

$2,900,000

  • 3 Beds
  • 2 Baths

  • 3,126 SqFt
  • 4.01 Acres

Single Family Residence

Not Applicable

Now Being Offered Is 15 Acres (approximately) Of Prime Real Estate. No Value In The Single Family Home Onsite. Just 20 Minutes From Downtown Orlando And Lake Nona. This Area Of East Orlando Is Growing By Leaps And Bounds. New Builds Are Within Short Walking Distance. And The Location Could Not Be Any Better With Easy Access To Sr 408 And Sr 417, The Oviedo Mall, Waterford Towers, And Shopping Centers Of Waterford Lakes Town Center. With Only A 5 Mile Drive To The University Of Central Florida. Price Reflects Both Parcels: 02-22-32-0000-00-02...

1508 Lake Shore Drive, ORLANDO

New Photo of Listing #O5993042

$2,850,000

  • 4 Beds
  • 3 Baths

  • 3,612 SqFt
  • 0.41 Acres

Single Family Residence

Rose Isle Sec 01

Rare Find In Desirable Rose Isle. This 4 Bedroom 3 Bath Home Was Completed In 2015. The Craftsman Style Exterior Of This Home Sits On A Large Lot Under A Towering Tree Canopy That Includes Oak And Cypress And Takes Full Advantage Of Views Of Beautiful Lake Rowena From Every Room. A Bird Watchers Retreat, Some 65 Plus Species Of Birds Have Been Observed From The Property, Among Them Bald Eagles, Wood Storks, Great Blue Herons, American Egrets And Many Others. Entering The Modern Interior Of The Home, The 12 Foot Ceilings Allow One's Eye To...

10379 Woodward Winds Drive, ORLANDO

New Photo of Listing #T3285358

$2,749,000

  • 4 Beds
  • 4 Baths
  • 1 Half

  • 6,766 SqFt
  • 0.55 Acres

Single Family Residence

Waters Edge/lk Nona

One Or More Photo(s) Has Been Virtually Staged. A Timeless Design, Combined With Construction Materials And Technological Enhancements, Make This Orlando Luxury Waterfront Residence A One-of-a-kind Estate. Built With Both Durability And Desirability, This Lakefront Home Represents An Eco-friendly Lifestyle That Minimizes Impact On The Environment While Maximizing Your Quality Of Life. Custom Built On Lake Nona In The Exclusive Waters Edge Residential Enclave Of 11 Waterfront Homes, This Incomparable Home And Stately Grounds Is A Building Ind...

811 North Lake Adair Boulevard, ORLANDO

New Photo of Listing #O5997300

$2,640,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 7,795 SqFt
  • 0.79 Acres

Single Family Residence

Hoffman Terrace

Elevated Expansive Property Overlooking Lake Adair With Views Of The Downtown Orlando Skyline. This Elegant College Park Estate, On Over ¾ Acre With 200+ Feet Of Frontage, Has All The Features For The Most Discerning Buyer. Boasting 5 Ensuite Bedrooms One Of Which Is Currently Appointed As An Office And Game Room W/ Kitchen And Separate Stairway. There Is A Spacious Private Downstairs Primary Suite With A Resort/spa Like Bathroom, 2 Large Walk-in Closets, And Beautiful Views Of The Back Yard. The Owner Has Done Many Updates To The Home I...

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 January 19th, 2022 at 10:53pm EST.