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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2,284 Properties Found. Showing Page 1 of 191
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10309 Summer Meadow Way, Orlando

Photo of Listing #O5828625

$7,945,000

  • 6 Beds
  • 6 Baths
  • 3 Half

  • 8,589 SqFt
  • 0.41 Acres

Single Family / Villa

Golden Oak Phase 3

New Four Seasons Private Residences Orlando At Walt Disney World® Resort Home For Sale- Inspired By Mid-century Modern Architectural Icons, This Gardenside Phil Kean Home Displays 8,589 Square Feet Of Indoor Space. Expansive Windows Throughout Are Perfect For Appreciating The Luscious Preserves And Charm Of The Community. 5 Bedrooms, 6 Full Baths, 3 Powder Rooms And 3-car Garage, With Each Room Showcasing Leading Edge Technology And Environmentally Sensitive Details. This Home Exhibits A “wow” Factor With Flowing Open Kitchen, Living And Fam...

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...

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, ...

9275 Point Cypress Dr, Orlando

Price
Reduced
Photo of Listing #O5801057

$3,999,000

  • 7 Beds
  • 6 Baths
  • 1 Half

  • 9,307 SqFt
  • 0.91 Acres

Single Family / Villa

Cypress Point

Unprecedented Opportunity At An Unprecedented Price. The Sellers Of This Spectacular Peninsula Property, Impossible To Replicate, Dueling Lake Frontage, Overlooking Disney Fireworks Are Relocating Out Of State And Have Priced This Unique Home For Half Its Cost In 2000 When Built, Priced Right For Fast Sale. Don’t Overlook This Real Deal On A Premium Tip Top Prime Location In Orlando The Secure And Private Location Inside Of The Highly Distinguished, Guard Gated Community Of Cypress Point Makes This An Unparalleled Opportunity For Privacy And...

10300 Pocket Ln, Orlando

Photo of Listing #O5792644

$3,600,000

  • 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...

9070 Mayfair Pointe Dr, Orlando

Photo of Listing #O5817770

$3,595,000

  • 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 ...

9100 Kilgore Rd, Orlando

Price
Reduced
Photo of Listing #O5755389

$3,380,000

  • 6 Beds
  • 7 Baths

  • 6,689 SqFt
  • 7.51 Acres

Single Family / Villa

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...

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...

10205 Tavistock Rd, Orlando

Price
Reduced
Photo of Listing #O5776734

$3,350,000

  • 6 Beds
  • 8 Baths
  • 1 Half

  • 8,986 SqFt
  • 2.03 Acres

Single Family / Villa

Lake Nona Ph 01a Prcl 07

Price Drop! Resurfaced Tennis Court- Nov 2019. Please View Our Virtual Tour To See All Photos! It's Not Just Living, It's A Lifestyle! Tom Price Architectural Design With Ray Coudriet As The Builder. Come See This Palatial Estate Of 8,986 Sf (includes 7,714 Sf Main House And 1,272 Sf Guest House) Located In The Coveted Lake Nona Estates And Situated On More Than 2 Acres Along The Par 3, Golf Hole Number 13 Of The Renowned, Tom Fazio-designed, Lake Nona Golf & Country Club. This Incredible Property Boasts Its Own Private Tennis Court With Per...

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 And Upgraded Appliances. An Impressive Private Formal Dining Room Is Situated Across From An 800-bottle Wine Cellar Lined With Custom Wood Holders. The Expansive Master Bedroom Features A Coffer...

5550 Osprey Isle Ln, Orlando

Price
Reduced
Photo of Listing #O5798236

$2,999,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 7,044 SqFt
  • 1.04 Acres

Single Family / Villa

Isle Of Osprey

Your Opportunity To Own This Magnificent French Country Lakefront Mansion Located On The World Famous Butler Chain Of Lakes In The Guard Gated Private Enclave Of Isle Of Osprey. This Stunning 5 Bed, 5.5 Bath Home Sits On An Over 1 Acre Lot With Uninterrupted Views Of Lake Chase. Transitional Luxury Boasting 9’ Hand Forged Cantera Front Doors, Stone & Brazilian Cherry Wood Floors, Custom 2-step Crown & Millwork, Elegant Double Tray Ceilings & Hand Painted Accents. The Kitchen Features 42” Maple Cabinets, Granite, Mahogany Butcher Block Island...

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 January 20th, 2020 at 9:15am EST.