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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2,308 Properties Found. Showing Page 1 of 193
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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...

9726 Kilgore Road, ORLANDO

New Photo of Listing #O5570091

$4,895,000

  • 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...

10074 Symphony Grove Dr, ORLANDO

New 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 ...

9227 Sloane Street, ORLANDO

New Photo of Listing #O5874942

$3,950,000

  • 5 Beds
  • 6 Baths
  • 2 Half

  • 8,209 SqFt
  • 0.90 Acres

Single Family Residence

Lake Nona Estates

This Beautifully Remodeled Estate Blends The Best Of Mediterranean Architecture With Contemporary Styling. Encompassing Almost One-acre Of Land, The Home’s Thoughtful Layout Uses The Expanse To Its Advantage. A Rotunda Foyer With Herringbone Floors Welcomes You Into This Residence, While The Views From The Formal Living Room Out To The Pool Deck Immediately Capture Your Attention. Just Past The Formal Dining Area And Wine Cellar, The Kitchen And Great Room Offer Space For Casual Meals And Relaxation. The Focal Point Of The Kitchen Is A Two-p...

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...

10300 Pocket Lane, ORLANDO

New 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 Drive, ORLANDO

New Photo of Listing #O5867267

$3,750,000

  • 4 Beds
  • 4 Baths
  • 1 Half

  • 6,100 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...

9506 Tavistock Road, ORLANDO

New Photo of Listing #O5879441

$3,450,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 5,406 SqFt
  • 0.55 Acres

Single Family Residence

Lake Nona Estates

Under Construction. Described As A Transitional Prairie Style, The Design For This Beautiful Single-story Home Was Heavily Influenced By Frank Lloyd Wright With An Emphasis On Nature, Craftsmanship And Simplicity. The Warmth Of This Residence Is Highlighted By The Natural Materials Used, Including Stacked Stone On Both The Interior And Exterior, Beautiful Vein-cut Stone Tile Accents And Light Oak Doors And Beams. The Clean Architectural Lines Of The House Create A Contemporary Feel And The Open Floor Plan Effortlessly Connects The Indoor And...

9548 Tavistock Road, ORLANDO

New 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...

10552 Kirby Smith Road, ORLANDO

New Photo of Listing #O5833735

$2,975,000

  • 7 Beds
  • 6 Baths
  • 1 Half

  • 5,679 SqFt
  • 4.97 Acres

Single Family Residence

Lake Whippoorwill - Hart...

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 ...

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, 2020 at 3:16am EDT.