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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1,176 Properties Found. Showing Page 1 of 98
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9236 Bay Point Drive, ORLANDO

New Photo of Listing #O5854037

$6,950,000

  • 6 Beds
  • 8 Baths
  • 2 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...

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...

7625 Clarcona Ocoee Road, ORLANDO

New Photo of Listing #O5923053

$5,500,000

  • 2 Beds
  • 2 Baths

  • 5,730 SqFt
  • 58.81 Acres

Single Family Residence

None

Beautiful Property Consits Of 4 Connected Parcels For Total 58.81 Acres. Mostly Cleared Pasture Land. Current Zoning A-1 Currently Has A Single Family Home With Indoor Pool And 3 Fireplaces, Concrete Barn 45x25, Pole Bulding 42x30, Horse Stable 39x26, Workshop, Mobile Home, 7625 Clarcona Ocoee Rd Orlando, Fl 32818-1215 (parcel: 35-21-28-0000-00-018) (4.96 Acres) 7466 Vivian Ln Orlando, Fl 32818 (parcel: 35-21-28-0000-00-015) (18.35 Acres) 6157 Gilliam Rd Orlando, Fl 32818 (parcel: 35-21-28-0000-00-035) (4.14 Acres) Clacona Ocoee Rd ...

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, ...

7500 Daetwyler Drive, ORLANDO

New Photo of Listing #O5846129

$3,750,000

  • 6 Beds
  • 6 Baths
  • 1 Half

  • 7,158 SqFt
  • 3.71 Acres

Single Family Residence

Silver Beach Sub

Lakefront - Back On Market! Contract Just Failed ! 3+ Acre Estate, 350' Waterfront - Completely Gated & Walled! Don't Miss It! New Price!! 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...

9188 Point Cypress Drive, ORLANDO

New Photo of Listing #O5934848

$3,595,000

  • 6 Beds
  • 7 Baths
  • 1 Half

  • 9,477 SqFt
  • 1.27 Acres

Single Family Residence

Cypress Point Ph 2

Exquisite, Butler Chain Estate Boasts Almost 9,500 Square Feet, Located On Lake Sheen In The Prestigious Guard-gated Community Of Cypress Point. Stunning Lake Views Provide The Backdrop For The Grand Foyer And Soaring 22-foot Ceilings. This Home Was Recently Remodeled And Is A True Entertainer's Dream From The First-floor Home Theater And Waterfront Game Room To The Second-floor Craft Room, Guest Suite And Bonus Room. The Renovated Kitchen Is Truly A Chef's Delight From The Top-of-the-line Stainless Steel Appliances To A Large Center Island ...

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...

7017 Via Carmel Way, ORLANDO

New Photo of Listing #O5928740

$3,300,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 6,182 SqFt
  • 0.51 Acres

Single Family Residence

Carmel By The Lk

Under Construction. Last Chance To Purchase In The Ultra-luxury Community Of Carmel! Relax In Your Very Own Paradise In This Custom 5 Bedroom, 5/1 Bathroom Two-story Home With Gorgeous Pool And Summer Kitchen - Built By Davila Homes, Parade Of Homes Grand Award Winner! Step Through The Double Doors Into A Modern And Elegant Foyer Where You Will Be Greeted By The Formal Living Spaces Complete With Intricate Ceiling Details, Grand Fireplace, And A Circular Wet Bar Providing The Perfect Space To Entertain Guests. The South Wing Of The Home Is S...

1027 Edgewater Drive, ORLANDO

New Photo of Listing #O5916234

$3,299,000

  • 5 Beds
  • 6 Baths
  • 2 Half

  • 7,434 SqFt
  • 0.60 Acres

Single Family Residence

Arthur William H

Past A Private Gated Entry, Fronted By A Circular Drive & Enveloped By Lush Grounds Sits A Magnificent Italian Renaissance-style Lakefront Estate Known As “chateau Les Grands Chenes,” Or “castle Of The Big Oak Trees.” This Exquisite 2000 Sebc Grand Aurora Award-winning Jewel Affords Unparalleled Luxury In A Premier Orlando Locale, With Rare Exposure On 2 Beautiful Lakes. Enjoy Lovely Views Of Lake Adair From The Front Of The Home As Well As Lake Concord & City Skyline From The Rear Property! Lake Concord Is A 65 Acre Ski Lake. Built-in 19...

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...

8527 Lake Nona Shore Drive, ORLANDO

New Photo of Listing #O5773491

$2,840,040

  • 5 Beds
  • 6 Baths
  • 1 Half

  • 6,174 SqFt
  • 0.35 Acres

Single Family Residence

Lake Nona Estates

Under Construction. Currently 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 ...

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 April 19th, 2021 at 4:07am EDT.