County: Orange County | Osceola County | Polk County | Lake County

Orange County Vacation Homes 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!

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Active

$25,000,000

CYPRESS POINT PH 02

9291 Point Cypress Dr, ORLANDO

12 Beds 15 Baths 14,706 SqFt Single Family Residence MLS® # O5965014

Active

$24,995,000

▼ $5,005,000 ACREAGE & UNREC

9508 Windy Ridge Rd, WINDERMERE

7 Beds 16 Baths 29,739 SqFt Single Family Residence MLS® # O6060999

Active

$23,300,000

▲ $5,300,000 GOODWINS ADD

110 West Jefferson St, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # OM650214

New

Active

$17,500,000

ISLEWORTH

9306 Blanche Cove Drive Dr, WINDERMERE

5 Beds 8 Baths 14,856 SqFt Single Family Residence MLS® # O6097686

Active

$17,486,000

▲ $1,500,000 TWELVE OAKS

1220 North Park Ave, WINTER PARK

7 Beds 7 Baths 12,475 SqFt Single Family Residence MLS® # O6012672

Active

$15,000,000

BENTLEY PARK 2ND REP

9200 Bentley Park Cir, ORLANDO

7 Beds 12 Baths 20,690 SqFt Single Family Residence MLS® # L4930944

Active

$11,995,000

RESERVE AT LAKE BUTLER SOUND

11301 Bridge House Rd, WINDERMERE

5 Beds 9 Baths 9,267 SqFt Single Family Residence MLS® # O6083126

Active

$10,950,000

ISLE OF SICILY

4 Isle Of Sicily, WINTER PARK

5 Beds 8 Baths 9,522 SqFt Single Family Residence MLS® # O6095179

Active

$9,500,000

GOLDEN OAK PH 01C

10030 Enchanted Oak Dr, GOLDEN OAK

6 Beds 7 Baths 9,444 SqFt Single Family Residence MLS® # O6017000

Active

$9,500,000

17802 Old Ymca Rd, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land MLS® # O5968921

Active

$8,500,000

▼ $1,150,000 0000

1190 North Park Ave, WINTER PARK

8 Beds 10 Baths 19,619 SqFt Single Family Residence MLS® # O6039038

Active

$8,250,000

▲ $750,000 MARINA BAY ESTATES

11035 Schooner Way, WINDERMERE

7 Beds 7 Baths 15,000 SqFt Single Family Residence MLS® # O5992601

Active

$8,250,000

▲ $1,255,000 METCALF PARK REP

11940 Lake Butler Blvd, WINDERMERE

5 Beds 7 Baths 6,549 SqFt Single Family Residence MLS® # O5992327

Active

$7,990,000

LAKE WHIPPOORWILL

10411 Tyson Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6081836

Active

$7,990,000

LAKE WHIPPOORWILL

10419 Tyson Rd, ORLANDO

3 Beds 2 Baths 3,300 SqFt Single Family Residence MLS® # O6080656

Active

$7,900,000

RESERVE AT LAKE BUTLER SOUND 45/120

11205 Bridge House Rd, WINDERMERE

6 Beds 8 Baths 8,330 SqFt Single Family Residence MLS® # O6088503

Active

$7,900,000

▼ $1,050,000 J KRONENBERGER SUB

1311 Via Tuscany, WINTER PARK

7 Beds 8 Baths 10,997 SqFt Single Family Residence MLS® # O6011692

Active

$7,800,000

GOLDEN OAK PHASE 5

10217 Symphony Grove Dr, ORLANDO

5 Beds 7 Baths 5,241 SqFt Single Family Residence MLS® # O6048451

New

Active

$7,500,000

ISLEWORTH

5139 Isleworth Country Club Dr, WINDERMERE

7 Beds 8 Baths 13,973 SqFt Single Family Residence MLS® # O6097345

Active

$7,495,000

▲ $6,745,500 LAKE DOWN ESTATES

10988 Down Yonder Ln, WINDERMERE

4 Beds 6 Baths 8,446 SqFt Single Family Residence MLS® # O6021133

Active

$7,388,000

ISLEWORTH

9736 Chestnut Ridge Dr, WINDERMERE

5 Beds 7 Baths 7,625 SqFt Single Family Residence MLS® # O6080321

Active

$7,250,000

▼ $525,000 ISLEWORTH

9832 Laurel Valley Dr, WINDERMERE

6 Beds 10 Baths 11,100 SqFt Single Family Residence MLS® # O6043474

Active

$7,035,000

LAKE BUTLER ESTATES

11947 Lake Butler Blvd, WINDERMERE

6 Beds 9 Baths 14,364 SqFt Single Family Residence MLS® # O6065698

Active

$7,000,000

ISLEWORTH

9838 Laurel Valley Dr, WINDERMERE

5 Beds 9 Baths 10,843 SqFt Single Family Residence MLS® # O6060724

Active

$6,995,000

▼ $505,000 ACREAGE & UNREC

9520 Windy Ridge Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6069467

Active

$6,750,000

▼ $1,209,000 SUNSET BAY REP

5020 Down Point Ln, WINDERMERE

8 Beds 8 Baths 9,621 SqFt Single Family Residence MLS® # O6030119

Active

$6,500,000

KEENES POINTE 46/104

9139 Tibet Pointe Cir, WINDERMERE

6 Beds 9 Baths 10,341 SqFt Single Family Residence MLS® # O6080288

Active

$6,500,000

▼ $1,400,000 MILLIONAIRE'S ROW

9726 Kilgore Rd, ORLANDO

5 Beds 9 Baths 12,370 SqFt Single Family Residence MLS® # O5570091

Active

$6,495,000

▼ $700,000 KEENES POINTE 46/104

6507 Rosella Ct, WINDERMERE

7 Beds 8 Baths 10,485 SqFt Single Family Residence MLS® # O6064654

Active

$6,395,000

METCALF PARK REP

11536 Lake Butler Blvd, WINDERMERE

6 Beds 8 Baths 8,204 SqFt Single Family Residence MLS® # O6094155

Active

$6,000,000

THE LAKE HOUSE

3801 Mckinnon Rd, WINDERMERE

6 Beds 15 Baths 24,080 SqFt Single Family Residence MLS® # O6090168

Active

$6,000,000

INTERNATIONAL COVE

6440 Canada Ave, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5347857

New

Active

$5,999,999

ISLEWORTH

9718 Green Island Cv, WINDERMERE

4 Beds 6 Baths 4,724 SqFt Single Family Residence MLS® # O6095851

Active

$5,995,000

▼ $455,000 RESERVE AT LAKE BUTLER SOUND 45/120

11049 Bridge House Rd, WINDERMERE

5 Beds 8 Baths 10,112 SqFt Single Family Residence MLS® # O6033684

Active

$5,850,000

▲ $1,729,000

N/A, APOPKA

0 Beds 0 Baths 6,562 SqFt Land MLS® # O5183153

Active

$5,805,000

1111 West Keene Rd, APOPKA

0 Beds 0 Baths 0 SqFt Land MLS® # O6086552

Active

$5,495,000

▼ $300,000 BEVERLY SHORES

3260 Lake Shore Dr, ORLANDO

5 Beds 9 Baths 6,709 SqFt Single Family Residence MLS® # O6076310

Active

$5,000,000

WP KELLY 11

3243 West Kelly Park Rd, APOPKA

0 Beds 0 Baths 0 SqFt Land MLS® # G5056961

Active

$4,999,990

MOSS PARK RESERVE

10330 Wittenberg Way, ORLANDO

6 Beds 8 Baths 9,272 SqFt Single Family Residence MLS® # O6029473

Active

$4,999,000

THOMAS M HENKELS ADD

466 Henkel Cir, WINTER PARK

4 Beds 5 Baths 4,416 SqFt Single Family Residence MLS® # O6094004

Active

$4,950,000

▼ $550,000 ISLEWORTH

6474 Deacon Cir, WINDERMERE

6 Beds 6 Baths 5,859 SqFt Single Family Residence MLS® # O6042860

Active

$4,900,000

▼ $90,000 NO HOA

9575 Westover Roberts Rd, WINDERMERE

9 Beds 8 Baths 8,464 SqFt Single Family Residence MLS® # O6060334

Active

$4,900,000

▲ $400,000 LAKESIDE ESTATES

5640 Santa Rosa Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5946302

Active

$4,900,000

OSCEOLA PLACE

550 Palmer Ave, WINTER PARK

5 Beds 8 Baths 5,952 SqFt Single Family Residence MLS® # O6029085

Active

$4,880,000

LIVINGSTON

1911 Silver Star Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6081664

Active

$4,699,995

ROSSER RESERVE REP

1005 Down Reserve Ct, WINDERMERE

6 Beds 8 Baths 9,754 SqFt Single Family Residence MLS® # O6053570

Active

$4,500,000

WINDERMERE REP

225 Magnolia St, WINDERMERE

7 Beds 11 Baths 5,735 SqFt Single Family Residence MLS® # O6079340

Active

$4,325,000

WINTER PARK TOWN OF

1106 Palmer Ave, WINTER PARK

4 Beds 6 Baths 6,256 SqFt Single Family Residence MLS® # O6043192

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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!

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