Orange County Vacation Home for Sale

News organization CNN has rated Orange County as a top ten world destination. It’s easy to see why. The Orange County vacation homes for sale offers residents and visitors friendly neighborhoods, year-round sunshine and world-renowned theme parks like Disney and SeaWorld. Also, there ares attractions along International Drive such as the Orlando Eye, the largest observation wheel on the East Coast.

The city of Orlando and a dozen other incorporated communities including Lake Buena Vista and Windermere are located within Orange County. The second largest convention center in the U.S. can be found here, as well as a wide range of shopping opportunities – from upscale boutiques to outlet stores, and a variety of restaurants featuring nearly every cuisine imaginable.

Orange County also features 99 different parks, trails and facilities with activities for just about anyone including horseback trails, water parks and canoeing along scenic rivers teeming with wildlife.


Check out the available Orange County – Orlando vacation real estate listings below, or continue reading to learn more about the many wonderful holiday communities found in the county!


Search Orange County Real Estate Listings

9291 POINT CYPRESS DR,

9291 Point Cypress Dr, Orlando

1215147062
Welcome to Entrelagos, an extraordinary estate located on a private peninsula between Lake Sheen and Lake Tibet on the prestigious Butler Ch …more
$25,000,000
10224 SUMMER MEADOW WAY,

10224 Summer Meadow Way, Golden Oak

6982142
Welcome to Capolavoro, an Italianate masterpiece located in the Four Seasons Private Residences within Golden Oak at Walt Disney World Resor …more
$16,385,000
Sold
9225 LAKE MABEL DR,

9225 Lake Mabel Dr, Orlando

913115652
This Palatial & Private Estate is an Architectural Masterpiece by Master Builder, Victoria Martoccia, & 2010’s Parade of Homes High End Cu …more
$12,500,000
Sold
9927 GIFFIN CT,

9927 Giffin Ct, Windermere

1215310002
!!!! Nestled in one of Central Florida’s most exclusive 24-hour privately gated golf communities, Isleworth, is a rare and unique sprawlin …more
$11,000,000
Sold
1000 GENIUS DR,

1000 Genius Dr, Winter Park

1012138552
Perfectly positioned along the shores of Lake Virginia and Lake Mizell on the Winter Park Chain of Lakes, this majestic Mediterranean estate …more
$10,650,000
Sold
1411 VIA TUSCANY,

1411 Via Tuscany, Winter Park

510107342
One of Winter Park’s most notable landmark properties defines architectural excellence in an inspiring renovation of a Tuscany vineyard esta …more
$10,500,000
Sold
10114 ENCHANTED OAK DR,

10114 Enchanted Oak Dr, Golden Oak

6890562
Welcome to The Beauvoir, surrounded by extravagance and comfort. Golden Oak at Walt Disney World® Resort is one of the most distinct and de …more
$8,500,000
11035 SCHOONER WAY,

11035 Schooner Way, Windermere

77150002
Pre-Construction. To be built. Where Art Meets Architecture! Build your Custom Dream Home with state of the art energy efficiency engineerin …more
$7,500,000
Sold
9718 CHESTNUT RIDGE DR,

9718 Chestnut Ridge Dr, Windermere

48110792
New Photos & Video Added! Poised on more than two acres along the shores of Lake Bessie, this extraordinary custom estate offers a prime lak …more
$7,120,000
1001 ANCHORAGE CT,

1001 Anchorage Ct, Winter Park

5792772
Magnificent New Custom Downtown Winter Park estate, built by one of the country’s top builders, this architectural masterpiece is situated …more
$6,995,000
11940 LAKE BUTLER BLVD,

11940 Lake Butler Blvd, Windermere

5765492
UNIQUE ESTATE HOME SET ON 300 FEET OF LAKE BUTLER SHORELINE WITH 300’ SEAWALL. This private, gated lakefront home is set on 2.4 acres in o …more
$6,995,000
Sold
5018 LATROBE DR,

5018 Latrobe Dr, Windermere

710123532
Gracious lakefront living at its finest, this exquisite French chateau offers a prime location along the shores of Lake Bessie within the re …more
$6,900,000

Living in Orange County

Orange County takes its name from the fruit that constituted its main product. At its peak in the 1970’s, some 80,000 acres of citrus were planted in the area. But damaging freezes took its toll on the industry, and agriculture gave way to tourism, thanks to the great success of Walt Disney World and Universal Studios. The county has also become a hotbed for industries specializing in advanced computer simulation and features a thriving life science research hub.

Orange County Real Estate Market

Orange County real estate caters to visitors from around the world. Many UK residents choose to spend their holidays in the area, particularly around Disney World. The warm weather also attracts snowbirds from northern states like Michigan, Ohio and New York every year. There are many beautiful single family homes available for purchase as a second home, but the county does not allow these homes to be rented out for the short-term.

Vacation home buyers typically choose properties near the theme parks because these Orange County areas feature condos and townhomes that are zoned for short-term rentals. There are several outstanding communities such as Floridays Orlando Resort and Blue Heron Beach Resort which offer condominiums for sale, and provide luxury living with resort-style amenities like water parks and restaurants on-site.

Windermere does have vacation homes, condos and townhomes for sale that are close to the attractions. But the city does not allow short-term rentals. Only certain areas of Orlando allow short-term rentals.


Are you interested in purchasing vacation property in Orange County? We encourage you to contact the Donovan Team online or give us a call at 407.705.2616 We’d be thrilled to help you find yourself a beautiful Orlando vacation home near Disney World!