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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1,344 Properties Found. Showing Page 1 of 112
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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...

10224 Summer Meadow Way, ORLANDO

New Photo of Listing #S5051535

$16,385,000

  • 6 Beds
  • 6 Baths
  • 3 Half

  • 8,214 SqFt
  • 0.41 Acres

Single Family Residence

Golden Oak Ph 3

Welcome To Capolavoro, An Italianate Masterpiece Located In The Four Seasons Private Residences Within Golden Oak At Walt Disney World Resort. Exceptional Luxury, Thoughtful Design, Impeccable Craftsmanship And Access To Unparalleled Services Provide The Perfect Opportunity To Immediately Create Meaningful Memories With Family And Friends. This An Incredible Chance To Purchase In The Now Sold Out Four Seasons Private Residences And Own A Property Within The Walt Disney World Resort. The Breath-taking Formal Living Room Greets You Just Beyond...

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 #O5967276

$5,795,000

  • 6 Beds
  • 6 Baths
  • 4 Half

  • 12,000 SqFt
  • 0.76 Acres

Single Family Residence

Lake Nona Estates

The Epitome Of All Things Luxury, This 12,000 Sq.ft. Akers Custom Homes Estate Features 6 Bedrooms, 6/4 Bathrooms, 4-car Plus Golf Cart Garage, & Comes Complete W/ Interior Guest Quarters. Located In The World Class Lake Nona Golf & Country Club On .76 Acres, This Elegant Property Is Simply Waiting For You To Call It Home. Magnificently Manicured Landscaping Leads You Up The Circular Driveway To A Grand, Custom Designed Double Door Entry Into A Towering Foyer. A Glittering Chandelier W/ Wood Inlayed Ceilings Adorns The Formal Dining Room To ...

5434 Osprey Isle Lane, ORLANDO

New Photo of Listing #O5904473

$5,450,000

  • 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...

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, ...

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...

601 East Jackson Street, ORLANDO

New Photo of Listing #O5959225

$3,495,000

  • 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...

9131 Southern Breeze Drive, ORLANDO

New Photo of Listing #O5962884

$3,495,000

  • 7 Beds
  • 6 Baths
  • 2 Half

  • 8,430 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 ...

8527 Lake Nona Shore Drive, ORLANDO

New Photo of Listing #O5773491

$3,450,000

  • 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 ...

1027 Edgewater Drive, ORLANDO

New Photo of Listing #O5943809

$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. This Exquisite 2000 Sebc Grand Aurora Award-winning Jewel Affords Unparalleled Luxury In A Premier Orlando Locale, With Rare Exposure To 2 Beautiful Lakes. Enjoy Lovely Views Of Lake Adair From The Front Of The Home As Well As Lake Access On Lake Concord & City Skyline Views From The Rear Property! Lake Concord Is A Private 65 Acre Ski Lake. Built-in 1924 & Imp...

8200 Firenze Boulevard, ORLANDO

New Photo of Listing #O5964340

$3,250,000

  • 6 Beds
  • 5 Baths
  • 1 Half

  • 4,562 SqFt
  • 0.38 Acres

Single Family Residence

Vizcaya Ph 01 45/29

This Completely Remodeled Luxurious 6-bed/6-bath Masterpiece On Big Sand Lake Has Everything On Your List: Soaring Ceilings? Check. Custom High-end Finishes In Every Room? Check. A Resort-style Pool, Private Boardwalk & Boathouse? Check, Fully Furnished Check & Check! This Home Combines A Beautiful Spanish-style Exterior With An Ultra-modern Interior, Where Absolutely No Detail Was Overlooked. Step Inside To Find Double-height Ceilings, Gorgeous Floors Throughout, Built-in Niches, Lots Of Natural Light And Views From Every Room. Your Fantast...

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 27th, 2021 at 5:04am EDT.