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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2,325 Properties Found. Showing Page 1 of 194
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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 Residence

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

Photo of Listing #O5854037

$7,095,000

  • 6 Beds
  • 8 Baths
  • 1 Half

  • 9,764 SqFt
  • 0.73 Acres

Single Family Residence

Bay Point

Virtual Home Tour: Https://youtu.be/avtdpdq0tle 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...

9011 Mayfair Pointe Dr, Orlando

Price
Reduced
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

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 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, ...

10074 Symphony Grove Dr, Orlando

Photo of Listing #O5872763

$3,975,000

  • 4 Beds
  • 4 Baths
  • 1 Half

  • 3,233 SqFt
  • 0.17 Acres

Single Family Residence

Golden Oak Phase 5

Golden Oak At Walt Disney World® Resort Home For Sale - Celebrating The Art And Craft Of Creating Livable Spaces, This Charming Cottage Is A Blend Of Beauty And Functionality. With Its Signature Craftsman Eaves, Natural Materials And Traditional Front Porch, The Home Exudes Casual Elegance. An Open Floorplan Invites Conversation While A Seamless Sightline Draws The Eye To The Cozy Outdoor Living Area, Pool And Spa. Price Inclusive Of $325,000 Furniture Package. Sold As Leaseback Only. Golden Oak At Walt Disney World® Resort Is A Residential ...

10300 Pocket Ln, Orlando

Photo of Listing #O5792644

$3,900,000

  • 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...

8987 Crichton Wood Dr, Orlando

Photo of Listing #O5867267

$3,500,000

  • 4 Beds
  • 4 Baths
  • 1 Half

  • 5,400 SqFt
  • 1.25 Acres

Single Family Residence

Bay Hill Sec 05a

Pre-construction. To Be Built. Phil Kean Concept Design For This Beautiful Home Are Ready And Available Upon Request. Enjoy Beautiful Days On Lake Tibet From This Spectacular Bay Hill Lakefront Lot On The Butler Chain Of Lakes. Build Your Dream Home In A Prime Location Just Minutes To The World Famous Arnold Palmer’s Bay Hill Club And Lodge, Restaurant Row, Orlando’s Best Shopping, Area Attractions, Major Roads, And “a” Rated Schools. If You Have Often Imagined Living On The Water, This Magnificent Lakefront Property Invites You To Bring You...

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 Residence

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...

9100 Kilgore Rd, Orlando

Price
Reduced
Photo of Listing #O5755389

$3,150,000

  • 6 Beds
  • 7 Baths

  • 6,689 SqFt
  • 7.51 Acres

Single Family Residence

Na

This Stunning Butler Chain Estate Is The Epitome Of Luxury Florida Lake Front Living. This Private Gated Enclave Is Perfectly Sited On Approximately 7.5 Acres Of Land With An Impressive 350 Ft Long Driveway And Approximately 165 Feet Of Shoreline On Lake Sheen. The Home Features 6 Bedrooms, 7 Bathrooms, A Home Office, A First-floor Theater Room, A Fitness Center Overlooking The Lake, And A Second-floor Bonus Room. From The Moment You Step Through The Front Doors Your Eyes Are Greeted By A Grand Staircase And Soaring 25 Foot Ceilings With Wal...

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 Residence

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 ...

4400 New Broad St, Orlando

Photo of Listing #O5847433

$2,999,999

  • 5 Beds
  • 5 Baths
  • 2 Half

  • 6,641 SqFt
  • 0.35 Acres

Single Family Residence

Baldwin Park Unit 1

One Of A Kind Estate Home On Highly Coveted New Broad St In Baldwin Park. Built By Goehring & Morgan For The International Builder's Show With Recent Updates By Current Homeowner Including Cutting Edge Technology, Quality Fixtures And Craftsmanship That Is Unsurpassed. Expect To To Be Impressed As You Enter The Home By The Exquisite Circular Foyer W/marble & Travertine Inlayed Flooring,high Coffered,barrel-vaulted And Beamed Ceilings, Custom Solid Doors,art Niches,extensive Moldings,plantation Shutters, Designer Fixtures,touchscreen Lighting...

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 Residence

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 ...

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 July 6th, 2020 at 6:45am EDT.