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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1,740 Properties Found. Showing Page 1 of 145
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9236 Bay Point Drive, ORLANDO

New Photo of Listing #O5854037

$7,095,000

  • 6 Beds
  • 8 Baths
  • 1 Half

  • 9,764 SqFt
  • 0.73 Acres

Single Family Residence

Bay Point

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...

9011 Mayfair Pointe Drive, ORLANDO

New Photo of Listing #O5775691

$5,988,888

  • 6 Beds
  • 6 Baths
  • 4 Half

  • 12,000 SqFt
  • 0.76 Acres

Single Family Residence

Lake Nona Estates

Adjacent To The 10th Fairway And Taking Full Advantage Of Its 0.76-acre Home Site, This Transitional Estate Offers Exceptional Modern Appointments Perfectly Balanced By Its Welcoming And Thoughtful Architecture. Designed By Nasrallah Architectural Group, This Home Was Built In 2014 By Akers Custom Homes. The Foyer Creates A Grand Sense Of Arrival With Custom-commissioned Entry Doors, 24-foot Ceilings And Onyx Inlay Flooring. Graceful Details Extend Into The Living Room, Outfitted With A Dual-sided Fireplace And A Built-in Onyx Bar With Custo...

13337 Kirby Smith Road, ORLANDO

New Photo of Listing #O5897456

$5,900,000

  • 5 Beds
  • 7 Baths
  • 1 Half

  • 9,609 SqFt
  • 4.22 Acres

Single Family Residence

N/a

One Or More Photo(s) Has Been Virtually Staged. Live The Dream On Lake Hart. Minutes To The Lake Nona Medical City, Oia, Golf Courses, Great Schools And Much More. This Private, One-of-a-kind Estate Has 300 Feet 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 And 1 Half Baths With Custom Finishes ...

8506 Lake Nona Shore Drive, ORLANDO

New Photo of Listing #O5916078

$5,750,000

  • 5 Beds
  • 6 Baths
  • 1 Half

  • 7,740 SqFt
  • 0.72 Acres

Single Family Residence

Lake Nona Estates

Pre-construction. To Be Built. Currently Under Construction By Devoe Custom Homes, This Stunning Two-story Estate Offers Unparalleled Privacy And Is Full Of Character, Elegance And Warmth. Located At The End Of A Cul-de-sac, The Well-organized Floor Plan Emphasizes Flowing, Open Space Connections Among The Main Living Areas And Is Outfitted To Offer The Highest Level Of Finishes. Using Every Opportunity To Embrace Its Lakeside Setting, Sliding Glass Doors And Oversized Windows Are Found In Every Room On The Ground Floor. The Living Room, Sha...

5434 Osprey Isle Lane, ORLANDO

New Photo of Listing #O5904473

$5,700,000

  • 5 Beds
  • 6 Baths
  • 1 Half

  • 10,676 SqFt
  • 0.92 Acres

Single Family Residence

Isle Of Osprey At Dr Phi...

Ultra Private Luxury Estate On The Butler Chain! This Astonishing, Custom-built 10,676 Sqft Home Features 5 Bedrooms, 6/1 Bathrooms, A Split Floor Plan With A Separate Master Wing, Two-story Home Office, Theater Room, Golf Simulator, And An Abundance Of Outdoor Living Space! Located Within Guard-gated Isle Of Osprey, On A Meandering Street With An Oak Canopy Reminiscent Of Old Florida, This Mediterranean-style Masterpiece Is Situated On A .92 Acre Lot With 145’ Of Waterfrontage On Lake Chase. The Home Exudes A Stately Presence With Lush Land...

9086 Mayfair Pointe Drive, ORLANDO

New Photo of Listing #O5899828

$5,500,000

  • 5 Beds
  • 5 Baths
  • 5 Half

  • 8,245 SqFt
  • 0.71 Acres

Single Family Residence

Lake Nona Estates

Welcome To Palm Court - The 2017 Nahb (national Association Of Home Builders) New American Home. Designed And Built By World Renowned And Multi-award Winning Builder And Architect, Phil Kean. Inspired By His Travels, And A Desire To Build A Luxury Home That Is Environmentally Conscious, Palm Court Is A Pod-style Home Which Allows The Homeowner To Open And Close Areas Of The Home As Needed. This Smart Planning Also Allows The Home To Open To The Main Courtyard At The Front Of The Home, And The Luxurious Pool Area At The Back Of The Home. 40-...

9726 Kilgore Road, ORLANDO

New Photo of Listing #O5570091

$4,888,000

  • 5 Beds
  • 6 Baths
  • 3 Half

  • 12,370 SqFt
  • 4.36 Acres

Single Family Residence

Millionaire's Row

Presenting Grande Oaks, And Perhaps There Is No Other Palatial Estate That Is Comparable. Custom Designed And Built By Celebrity Singer Who Had Grandiose Ideas On What Was Exciting And Needed For One's Home. Many Special Features Stand Out, But One Is The Over Million Dollar Pool And Entertainment Area. One Will Think They Are At A Theme Park! This Home Has A Walk-in Closet Off Of The Mbr, 700' In Size. Forget Ever Parting With Anything! What A Pleasure It Will Be To Have A New Owner Love This Fine 4.36+ Acre Butler Chain Estate With - Yes, ...

9209 Cromwell Park Place, ORLANDO

New Photo of Listing #O5887498

$4,500,000

  • 6 Beds
  • 6 Baths
  • 4 Half

  • 10,773 SqFt
  • 1.20 Acres

Single Family Residence

Lake Nona

3d Virtual Tour Here - Bit.ly/9209cromwellparkplacevirtualtour - This Luxurious, Private Estate Is Located In The Golfer's Paradise Community Of Lake Nona Golf & Country Club And Is Masterfully Designed With Uncompromising Detail. Nestled Among An 18-hole Championship Tom Fazio Course, The Home Underwent A Major Renovation In 2017 That Infused New Life And Modernization Into This Tranquil Treasure. Six Bedrooms, Six Full And Four Half Baths With 10,773 Square Feet Of Living Space Welcomes You Into This Beautifully Planned Home. The Cul-de-sa...

7500 Daetwyler Drive, ORLANDO

New Photo of Listing #O5846129

$3,900,000

  • 6 Beds
  • 6 Baths
  • 1 Half

  • 7,158 SqFt
  • 3.71 Acres

Single Family Residence

Silver Beach Sub

Imagine This.... Walking Into A Beautiful, Furnished, Lakefront Home On 3.7 Acres - And Not Having To Do Anything But Just Move In And Start Enjoying! Completely Gated, With Privacy Walls, Maximum Security, And An Impressive Gated Entrance. The Views Are Awesome From An Open Interior With Soaring Ceilings And Oversized Windows! The Interior Is Dramatic And The Panoramic Views Are Seen From Almost Every Room! Completely Renovated! Just Like New !! You Won't Believe This Price When You See This Impressive Lakefront Estate. A Drea...

9116 Point Cypress Drive, ORLANDO

New Photo of Listing #O5903317

$3,595,000

  • 6 Beds
  • 6 Baths
  • 2 Half

  • 8,460 SqFt
  • 1.10 Acres

Single Family Residence

Cypress Point

Welcome To La Casa Burt. An Exquisite Privately Gated Estate Within One Of The Areas Most Exclusive Gated Communities. A Retreat Like No Other In A Place Like No Other, This Luxury Estate Envelops You Dramatically With The Feel Of A Tropical Oasis On The Central American Coast. The Private Gate At The Perimeter Of The Lushly Landscaped 1.1 Acre Property - Built By Rial Jones - On The Famed Butler Chain Of Lakes Is Designed By Metal And Glass Artists And Sets The Tone For The Supremely Opulent Designs And Quality Finishes Found All Over The H...

10300 Pocket Lane, ORLANDO

New Photo of Listing #O5792644

$3,499,000

  • 5 Beds
  • 5 Baths

  • 6,446 SqFt
  • 2.64 Acres

Single Family Residence

Willis R Mungers Land Sub

Home Consists Of 4 Split Level Living Areas Of Around 6500 Sq Ft Surrounding A Central Enclosed 6619 Sq Ft Enclosed Lanai With Pool, Spa And Used For Recreation. Home Is On A Peninsula On The Butler Chain Of Lakes And Very Close To The Water On All Sides. The Fish-pocket Canal Runs Through The Property, And There Is A Bridge Across The Canal And A Boardwalk On The Other Side - There Are Around 1000 Feet Of Water Frontage Just On The House Side Of The Canal. This Is A Spectacularly Unique, Private Gated Property With A Polynesian Style Home...

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 22nd, 2021 at 7:29pm EST.