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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1,012 Properties Found. Showing Page 1 of 85
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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...

9726 Kilgore Road, ORLANDO

New Photo of Listing #O5570091

$7,900,000

  • 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, ...

10205 Tavistock Road, ORLANDO

New Photo of Listing #O6027000

$7,000,000

  • 6 Beds
  • 8 Baths
  • 1 Half

  • 8,986 SqFt
  • 2.03 Acres

Single Family Residence

Lake Nona Ph 01a Prcl 07

Privacy, Space & Views! Not Another Lot Like This One Inside Lake Nona Golf & Country Club! Over 2 Acres, Main House, Guest House, Private Tennis Court, Private Pool & Personal Gym, All Overlooking A Glistening Pond & The Entire Par 3, Tee To Green, Hole 13. Enjoy Pond & Conservation Views From The Front Of The Home As Well. This Palatial Estate By Architect Tom Price And Builder Ray Coudriet, Offers Nearly 9,000 Sf Including A 7,700 Sf Main House & 1,300 Sf Guest House, Both Spacious, Grand & Offer Tremendous Space For Living & Entertaining...

10012 Hyperion Lane, ORLANDO

New Photo of Listing #O6015372

$6,395,000

  • 4 Beds
  • 5 Baths
  • 1 Half

  • 5,524 SqFt
  • 0.43 Acres

Single Family Residence

Golden Oak Ph 4

Welcome To Hyperion’s Little Glass House, A Home Like No Other. Nestled Behind The Manned Guard Gates Of The Famed Golden Oak At Walt Disney World, This Enchanted Estate Embodies Magic Behind Every Door. Built By Renowned, Award-winning Custom Home Builder Jones Clayton, This Estate Was Expertly Crafted To Embody The Essence Of Walt Disney Himself. The Little Glass House Earned Its Name From The Builder For Its Indoor/outdoor Feel And Extravagant Windows With Picturesque Views. Featuring 4 Bedrooms, 5 Bathrooms, Miele Appliances, Full Home A...

6049 Lady Bet Drive, ORLANDO

New Photo of Listing #O6012216

$3,400,000

  • 5 Beds
  • 6 Baths

  • 5,434 SqFt
  • 0.66 Acres

Single Family Residence

Pointe Tibet Rep

Snap Villas Presents This Contemporary Architecture Offer The Perfect Blend Of Elegance With Privacy And Functional Living. Point Tibet Is Situated Between The Butler Chain Of Lakes And The World Renowned Bay Hill Country Club. No Detail Is Overlooked, As Evidenced In The Custom Features, Including Stone Flooring, Custom-built Furniture, Advanced Technology, And Entertainment Systems. It Is A Piece Of Art. The Sliders Off The Family Room And Game Room, Open To Create A Seamless Flow To The Outdoor Living And Entertaining Areas. The First-flo...

4575 New Broad Street, ORLANDO

New Photo of Listing #O6026285

$3,125,000

  • 4 Beds
  • 5 Baths
  • 3 Half

  • 6,138 SqFt
  • 0.31 Acres

Single Family Residence

Baldwin Park Ut 01 50 121

Custom Built By Derek Builders, This Magnificent Baldwin Park Home Offers Over 6,000 Sf Of Fabulous Living Space And Perched On A Prime Location In Baldwin Park! The Oversized Corner Lot Is Approximately 1/3 Of An Acre, With An Expansive Covered Front Brick Patio That Overlooks The Park And Water Feature In The Middle Of New Broad Street. This Home Has More Bells And Whistles, High-end Finishes, And A Functional, Ideal Floorplan For All Your Needs. Wrapped In A Brick Wall With Multiple Covered Living Spaces, The Backyard Is A Private Oasis...

6018 Tarawood Drive, ORLANDO

New Photo of Listing #O6018106

$2,970,000

  • 6 Beds
  • 5 Baths
  • 2 Half

  • 5,806 SqFt
  • 0.43 Acres

Single Family Residence

Bay Hill

Magnificent Home Set Directly On 3rd Tee Overlooking A Lake In Arnold Palmer’s Bay Hill Golf Community. This Superb Home Boasts Over 5800 Sq Ft With Roaring 12 Ft Ceilings Throughout The First Floor And 1o Ft Ceilings On Second Floor. This Home Offers 6 Bedrooms, 5 Bathrooms And 2 Half Baths. Upon Entering You Will Find The Dining Room, Butler’s Pantry And The Massive Kitchen With Large Island. The Open Concept Kitchen, Eating Area And Family Room Over Look The Pool, Golf Course And Lake. The Master Suite Is Located On The First Floor, Has 2...

5558 Brookline Drive, ORLANDO

New Photo of Listing #O6005302

$2,900,000

  • 5 Beds
  • 4 Baths
  • 1 Half

  • 5,822 SqFt
  • 0.42 Acres

Single Family Residence

Bay Hill Sec 10

Location, Location, Location! A Golf Lover’s Dream Home, With A Beautiful Course View Of Holes 4 And 5, On One Of The Best Lots On Arnold Palmer’s Bay Hill Golf & Country Club. This Home Is Just Minutes Away From Great Attractions Like Shopping, Restaurants, And More! Set In A Great Community, This Home Is Near High-rated Schools And The Great Entertainment Of The Dr.philips Area. The 5,822 Square Foot Custom Home Has 5 Bedrooms, 4.5 Bathrooms, 0.42 Acres Lot, A Four-car Garage, And A Home Theater With 8 Deluxe Seats And Brand New Equipment,...

9242 Cypress Cove Drive, ORLANDO

New Photo of Listing #O6004590

$2,750,000

  • 4 Beds
  • 4 Baths

  • 5,063 SqFt
  • 0.72 Acres

Single Family Residence

South Bay Sec 1

One Of The Best Lots In South Bay Is Now Available For Sale And It Comes With A House!. Completely Unobstructed Water Views Right In The Middle Of The East Border Of Lake Tibet, Part Of The Most Desirable Chain Of Lakes In Orlando, This Location Gives You Perfect Over The Water Sunset And Firework Views Every Single Day. With The Butler Chain Encompassing 13 Interconnected Lakes, Over 5,000 Acres In Surface Water And 32 Navigable Canals; There Will Always Be Something To Discover When Leaving From Your Own Backyard And Private Dock, And With...

1204 41st Street, ORLANDO

New Photo of Listing #S5065318

$2,675,000

  • 3 Beds
  • 2 Baths

  • 1,590 SqFt
  • 10.00 Acres

Single Family Residence

Armstrong Acres

Welcome To Paradise Island! This Beautiful Private Gate Access 10 Acres Private Estate That Consist Of 8 Acres Of 4 Single Family Homes With 2 Acres Of Cleared Vacant Land Ready For Development. Current Tenant Is On A Month To Month Lease And Subleases All 4 Homes, Current Income Is $8000 Per Month And Has Always Paid On Time. Tenant Has Been At The Property For 8 Years . Enjoy Beautiful Country Living In The City 10 Minutes To Downtown Orlando And Access To All Major Highways And Shopping And Theme Parks. The 10 Acre Estate Consists Of ...

8967 Easterling Drive, ORLANDO

New Photo of Listing #O5987453

$2,595,000

  • 5 Beds
  • 5 Baths
  • 1 Half

  • 5,734 SqFt
  • 0.44 Acres

Single Family Residence

Bay Hill Sec 05

One Or More Photo(s) Has Been Virtually Staged. Pre-construction. To Be Built. Pre-construction. To Be Built. Located In The Heart Of Dr. Phillips At Bay Hill, Arya Custom Homes Brings You A One-of-a-kind Contemporary Masterpiece. The Attention To Detail And Over-the-top Finishes Of The Interior Captivates The Eye At Every Corner. This Elegant Modern New Construction With 5734sq. Ft House Sits On Large Lot In Bay Hill Neighborhood. Replete With Luxury And Functionality, This New Construction Features An Architecturally Designed. Spacious Out...

4036 Grande Brick Loop 7, ORLANDO

New Photo of Listing #O5982469

$2,581,950

  • 3 Beds
  • 3 Baths
  • 1 Half

  • 2,799 SqFt
  • 0.07 Acres

Condo - Hotel

Ritz-carlton Residences,...

Pre-construction. To Be Built. ***pre-construction To Be Built*** Unicorp National Developments, One Of The Fastest Growing And Most Dynamic Developers In The Nation Has Partnered With Local Master Custom Builder, Jones Clayton Construction To Bring Orlando’s First And Only Ritz-carlton Residences To The Market. This Private, Gated Enclave Of Luxury Living Is Redefining Orlando As A Destination. The Privilege Of Ownership Offers A New Level Of Luxury Lifestyle Blending The Legendary Service Of The Ritz-carlton Brand That Revolves Around 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 May 22nd, 2022 at 9:03am EDT.