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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2,449 Properties Found. Showing Page 1 of 205
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10243 Summer Meadow Way, Orlando

Photo of Listing #O5764867

$7,785,000

  • 6 Beds
  • 7 Baths
  • 3 Half

  • 8,516 SqFt
  • 0.41 Acres

Single Family / Villa

Golden Oak Ph 3

New Four Seasons Private Residences Orlando At Walt Disney World® Resort Home For Sale- A Custom Italianate Inspired Manor, Casa Serena, Greets Guests With A Grand Gallery Featuring Elegant Picture Windows Overlooking The Pool, Veranda And The Backdrop Of Lush Conservation In The Distance. Ideal For Entertaining, The Beautiful Open Kitchen And Great Room Offer A Spacious Area To Gather Which Open Up To An Outdoor Living Area With Summer Kitchen. The Circular Grand Stairway Leads To The Upstairs Quarters Which Feature An Abundance Of Balconie...

9236 Bay Point Dr, Orlando

New Photo of Listing #O5854037

$7,095,000

  • 6 Beds
  • 8 Baths
  • 1 Half

  • 9,764 SqFt
  • 0.73 Acres

Single Family / Villa

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 Dr, Orlando

Photo of Listing #O5775691

$6,599,000

  • 6 Beds
  • 6 Baths
  • 4 Half

  • 12,000 SqFt
  • 0.76 Acres

Single Family / Villa

Lake Nona Estates

Taking Full Advantage Of Its 0.76-acre Golf-front Home Site, This Transitional Estate Offers Modern Appointments Balanced By Welcoming And Thoughtful Architecture. Designed By Nasrallah Architectural Group, The Home Was Built In 2014 By Akers Custom Homes. The Stunning 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 Custom Cabinetry. The Residence Is Centered O...

9726 Kilgore Rd, Orlando

Price
Reduced
Photo of Listing #O5570091

$4,900,000

  • 5 Beds
  • 6 Baths
  • 3 Half

  • 12,370 SqFt
  • 4.36 Acres

Single Family / Villa

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 Ln, Orlando

Photo of Listing #O5792644

$3,900,000

  • 5 Beds
  • 5 Baths

  • 6,446 SqFt
  • 2.64 Acres

Single Family / Villa

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...

9548 Tavistock Rd, Orlando

Photo of Listing #O5813212

$3,350,000

  • 8 Beds
  • 8 Baths
  • 3 Half

  • 9,300 SqFt
  • 0.81 Acres

Single Family / Villa

Lake Nona Ph 01a Prcl 04...

Impressive Architectural Styling Complements The Stately Lines Of Georgian Design Throughout This Stunning, 9,300-square-foot Estate. Embracing Unparalleled Views Of Hole #3 Of Lake Nona Golf & Country Club’s Championship Golf Course, This Residence Celebrates All That Resort-style Living Has To Offer. Expanded In 2003, This Two-story Floor Plan Was Recently Updated With New Interior Paint, Flooring And Cabinetry. With Eight Bedrooms, Eight Full And Three Half Bathrooms, Including A Separate Guest Suite, This Spacious Layout Provides Ample P...

9070 Mayfair Pointe Dr, Orlando

Price
Reduced
Photo of Listing #O5817770

$3,295,000

  • 5 Beds
  • 6 Baths
  • 2 Half

  • 8,676 SqFt
  • 0.61 Acres

Single Family / Villa

Lake Nona Estates

Surrounded By Panoramic Golf And Water Views, This Two-story Home Sits On Over Half An Acre Of Land And Is Truly A Masterfully Crafted Estate. Distinguished By Spectacular Exterior And Interior Architectural Elements, This Transitional Residence Was Built For Both Entertaining And Comfortable Living. Travertine Floors With Wood And Tile Inlay Travel From The Foyer Throughout The Main Living Areas And Are Further Enhanced By Custom Wall Treatments, Columns And Beautiful Woodwork. The Fully Renovated Kitchen Is A Chef’s Delight With Thermador ...

9580 Sloane St, Orlando

Photo of Listing #O5808917

$3,100,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 8,263 SqFt
  • 0.46 Acres

Single Family / Villa

Lake Nona Ph 01a Prcl 11

Immerse Yourself In Luxury From The Moment You Enter The Grand Two-story Foyer Of This Immaculately Maintained Estate. An Elegant Formal Living Room Welcomes You With Stunning Double-height Windows, A Gas Fireplace And Spectacular Golf And Water Views. Relax In The Oversized Family Room Attached To A State-of-the-art Kitchen With Granite Counter Tops, Upgraded Appliances And A Hidden Pantry. An Impressive Private Formal Dining Room Is Situated Across From An 800-bottle Wine Cellar Lined With Custom Wood Holders. The Expansive Master Bedroom ...

9204 Cromwell Woods Sq, Orlando

Photo of Listing #O5799383

$2,995,000

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 5,698 SqFt
  • 0.51 Acres

Single Family / Villa

Lake Nona

Under Construction. Elegantly Crafted With Strong Architectural Lines, This Magnificent Estate Is Currently Under Construction By Devoe Custom Homes. Remarkably Close To Club Amenities, Yet Private In Location, This Five-bedroom, Five-full-and-two-half-bathroom Home Offers A Sleek Modern Aesthetic On Over Half An Acre. Timeless Materials Used Throughout The Interior And Exterior, Including Beautiful Stone And Rich Hardwoods, Provide A Neutral Palette For The Personalization Of Design And Décor. Ten-foot, Double-entry Front Doors Welcome You ...

10552 Kirby Smith Rd, Orlando

Photo of Listing #O5833735

$2,975,000

  • 7 Beds
  • 6 Baths
  • 1 Half

  • 5,679 SqFt
  • 4.97 Acres

Single Family / Villa

Lake Whippoorwill

Escape To Your Own Private Retreat Every Day With This Recently Updated, Custom Built Lakefront Estate, Including Separate Guest House, Boat Dock And Lift. This Magnificent Property Combines 2 Separate Parcels On 7 Privately Gated Acres (2 Of Which Extend Into Lake Whippoorwill). Perfectly In Sync With Its Sunny Florida Environment, This Labor Of Love Was Designed By A European Designer And Decorator. The Blend Of Mediterranean Architecture With Industrial Farmhouse And Transitional Interior Design Is The Epitome Of Indoor-to-outdoor Living ...

150 E Robinson St #ph3501, Orlando

Price
Reduced
Photo of Listing #O5827506

$2,900,000

  • 4 Beds
  • 3 Baths
  • 2 Half

  • 3,172 SqFt
  • 1.31 Acres

Condo / Apartment

Vue At Lake Eola Condo

Most Coveted Penthouse In Central Florida Is Now Available!! Perfectly Located On The Southeast Side Of The Top Floor At The Vue, This 4 Bedroom Penthouse Boasts Unrivaled Views Of Lake Eola & Downtown Orlando. It Is Evident From The Moment You Walk Through The Door That This Home Is Truly One Of A Kind. Floor To Ceiling Thermal Windows Surround The Open Living Space And Command Unparalleled, Incredible Views Of The City Beautiful. The Gourmet Kitchen Features Granite Countertops And Top-of-the-line Luxury Appliances. Each Bedroom Overlooks ...

8527 Lake Nona Shore Dr, Orlando

Photo of Listing #O5773491

$2,840,040

  • 5 Beds
  • 6 Baths
  • 1 Half

  • 6,174 SqFt
  • 0.35 Acres

Single Family / Villa

Lake Nona Estates

Under Construction. This Two-story Contemporary Residence By Barcellona Homes 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 Spa...

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 5th, 2020 at 4:45am EDT.