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Orange County Vacation Homes for Sale

CountyOrange County | Osceola County | Polk County | Lake County

Orange County ResortsBlue Heron Beach ResortFloridays Resort OrlandoGolden Oak at Walt Disney World - Hawthorn Suites Orlando Lake Buena VistaIsles At Cay CommonLake Buena Vista Resort Village & SpaParadiso Grande - Parc Corniche - Point OrlandoStaySky Suites I-Drive OrlandoThe Enclave Suites Orlando - The Grove Resort Orlando - Vista CayWorldquest Resort

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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FEATURED
Active 5025 Shoreway Loop 202, ORLANDO

$599,950

VISTA CAY

5025 Shoreway Loop 202, ORLANDO

3 Beds 2 Baths 2,001 SqFt Condominium MLS® # S5116690
FEATURED
Active 13427 Blue Heron Beach Dr 1901, ORLANDO

$389,900

▼ $9,050 BLUE HERON BEACH RESORT

13427 Blue Heron Beach Dr 1901, ORLANDO

2 Beds 2 Baths 1,165 SqFt Condo - Hotel MLS® # S5110829
FEATURED
Active 12539 Floridays Resort Drive 305-d, ORLANDO

$244,900

FLORIDAYS RESORT

12539 Floridays Resort Drive 305-d, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5105392
FEATURED
Active 8112 Poinciana Blvd 1706, ORLANDO

$225,000

LAKE BUENA VISTA RESORT

8112 Poinciana Blvd 1706, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5112618
FEATURED
Active 12527 Floridays Resort Dr E-103, ORLANDO

$214,950

▼ $5,000 FLORIDAYS RESORT

12527 Floridays Resort Dr E-103, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5114808
FEATURED
Active 8125 Resort Village Dr 5705, ORLANDO

$199,950

LAKE BUENA VISTA RESORT

8125 Resort Village Dr 5705, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5106607
FEATURED
Active 8125 Resort Village Dr 5814, ORLANDO

$179,950

▼ $30,000 LAKE BUENA VISTA RESORT

8125 Resort Village Dr 5814, ORLANDO

3 Beds 2 Baths 1,231 SqFt Condo - Hotel MLS® # S5113240
New FEATURED
Active 7601 Canada Ave 405, ORLANDO

$115,000

STAYSKY SUITES, HAWTHORN SUITES

7601 Canada Ave 405, ORLANDO

1 Bed 1 Bath 542 SqFt Condo - Hotel MLS® # S5118799
Active 6447 Grand National Dr, ORLANDO

$21,750,000

▲ $2,000,000 SHOPPERS WORLD

6447 Grand National Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6249921
Active 17802 Old Ymca Rd, WINTER GARDEN

$16,000,000

▲ $4,000,000

17802 Old Ymca Rd, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land MLS® # O5968921
Active 9621 Windy Ridge Rd, WINDERMERE

$15,950,000

▲ $2,000,000 WINDSOR HILL

9621 Windy Ridge Rd, WINDERMERE

9 Beds 16 Baths 20,445 SqFt Single Family Residence MLS® # O6184943
Active 10151 Enchanted Oak Dr, GOLDEN OAK

$14,500,000

▲ $700,000 GOLDEN OAK PH 1C

10151 Enchanted Oak Dr, GOLDEN OAK

7 Beds 9 Baths 10,742 SqFt Single Family Residence MLS® # O6143312
Active 4200 Down Point Ln, WINDERMERE

$12,900,000

▼ $1,000,000 DOWN POINT SUB

4200 Down Point Ln, WINDERMERE

6 Beds 9 Baths 14,435 SqFt Single Family Residence MLS® # O6176070
Active 17017 Marsh Rd, WINTER GARDEN

$12,000,000

NONE

17017 Marsh Rd, WINTER GARDEN

6 Beds 6 Baths 6,977 SqFt Single Family Residence MLS® # O6254855
Active 6149 Grosvenor Shore Dr, WINDERMERE

$11,999,999

KEENES POINTE

6149 Grosvenor Shore Dr, WINDERMERE

6 Beds 8 Baths 6,783 SqFt Single Family Residence MLS® # O6233554
Active 11301 Bridge House Rd, WINDERMERE

$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 1120 Preserve Point Dr, WINTER PARK

$11,900,000

WINDSONG-PRESERVE POINT

1120 Preserve Point Dr, WINTER PARK

7 Beds 11 Baths 11,255 SqFt Single Family Residence MLS® # O6269585
Active 1955 South Apopka Vineland Rd, ORLANDO

$11,800,000

1955 South Apopka Vineland Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6211968
Active 9832 Laurel Valley Dr, WINDERMERE

$11,749,000

▼ $746,000 ISLEWORTH

9832 Laurel Valley Dr, WINDERMERE

6 Beds 10 Baths 11,100 SqFt Single Family Residence MLS® # O6211352
Active 2661 Via Tuscany, WINTER PARK

$10,999,999

WINTER PARK

2661 Via Tuscany, WINTER PARK

4 Beds 5 Baths 4,564 SqFt Single Family Residence MLS® # O6260493
Active 4212 Hogshead Rd, APOPKA

$10,000,000

4212 Hogshead Rd, APOPKA

0 Beds 0 Baths 0 SqFt Land MLS® # O6269607
Active 2584 West Kelly Park Rd, APOPKA

$10,000,000

2584 West Kelly Park Rd, APOPKA

0 Beds 0 Baths 0 SqFt Land MLS® # O6238898
Active 11947 Lake Butler Blvd, WINDERMERE

$9,998,500

LAKE BUTLER ESTATES

11947 Lake Butler Blvd, WINDERMERE

6 Beds 9 Baths 14,364 SqFt Single Family Residence MLS® # O6239481
Active 11103 Bridge House Rd, WINDERMERE

$9,950,000

RESERVE AT LAKE BUTLER SOUND 45/120

11103 Bridge House Rd, WINDERMERE

5 Beds 6 Baths 9,403 SqFt Single Family Residence MLS® # O6266876
Active 9726 Kilgore Rd, ORLANDO

$9,900,000

▼ $20,000,000 N/A

9726 Kilgore Rd, ORLANDO

4 Beds 6 Baths 10,010 SqFt Single Family Residence MLS® # O6229408
Active Moss Park Rd, ORLANDO

$8,900,000

Moss Park Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5903841
Active 9343 Tibet Pointe Cir, WINDERMERE

$8,790,000

KEENES POINTE UNIT 03 46/104

9343 Tibet Pointe Cir, WINDERMERE

8 Beds 10 Baths 8,362 SqFt Single Family Residence MLS® # O6264629
New
Active 10443 Los Feliz Dr, ORLANDO

$8,250,000

GOLDEN OAK PH 4

10443 Los Feliz Dr, ORLANDO

5 Beds 8 Baths 5,475 SqFt Single Family Residence MLS® # O6273583
Active 5507 Worsham Ct, WINDERMERE

$8,200,000

▼ $450,000 ISLEWORTH

5507 Worsham Ct, WINDERMERE

5 Beds 11 Baths 10,200 SqFt Single Family Residence MLS® # O6180706
Active 17902 Seidner Rd, WINTER GARDEN

$7,900,000

LAKE AVALON GROVES REP

17902 Seidner Rd, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land MLS® # O6261785
Active 10424 Pocket Ln, ORLANDO

$7,889,995

▼ $5 WILLIS R MUNGERS LAND SUB

10424 Pocket Ln, ORLANDO

5 Beds 7 Baths 7,500 SqFt Single Family Residence MLS® # O6219322
Active 12422 Park Ave, WINDERMERE

$7,500,000

CHAINE DU LAC

12422 Park Ave, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O6215015
Active 17999 Old Ymca Rd, WINTER GARDEN

$7,500,000

17999 Old Ymca Rd, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land MLS® # O6202825
Active 1400 Alabama Dr, WINTER PARK

$6,950,000

▼ $550,000 J KRONENBERGER SUB

1400 Alabama Dr, WINTER PARK

5 Beds 9 Baths 7,916 SqFt Single Family Residence MLS® # O6212012
Active 9164 Point Cypress Dr, ORLANDO

$6,750,000

CYPRESS POINT

9164 Point Cypress Dr, ORLANDO

5 Beds 8 Baths 7,631 SqFt Single Family Residence MLS® # O6243016
Active 5518 Worsham Ct, WINDERMERE

$6,650,000

▼ $250,000 ISLEWORTH

5518 Worsham Ct, WINDERMERE

5 Beds 8 Baths 8,203 SqFt Single Family Residence MLS® # O6227090
Active 9301 Tibet Pointe Cir, WINDERMERE

$6,500,000

KEENES POINTE 46/104

9301 Tibet Pointe Cir, WINDERMERE

5 Beds 7 Baths 7,405 SqFt Single Family Residence MLS® # O6263524
Active 14154 Ward Rd, ORLANDO

$6,500,000

LAKE PRESERVE

14154 Ward Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # S5102984
New
Active 9743 Lounsberry Cir, GOLDEN OAK

$6,250,000

GOLDEN OAK PH 1B

9743 Lounsberry Cir, GOLDEN OAK

6 Beds 7 Baths 4,668 SqFt Single Family Residence MLS® # O6272053
Active 541 Virginia Dr, WINTER PARK

$6,250,000

TIMBERLANE SHORES

541 Virginia Dr, WINTER PARK

4 Beds 4 Baths 4,725 SqFt Single Family Residence MLS® # O6268853
Active 9105 Sheen Sound St, ORLANDO

$5,995,000

▲ $500,000 LAKE SHEEN SOUND

9105 Sheen Sound St, ORLANDO

5 Beds 8 Baths 7,147 SqFt Single Family Residence MLS® # O6261887
Active 9721 Carillon Park Dr, WINDERMERE

$5,990,000

▼ $410,000 KEENES POINTE

9721 Carillon Park Dr, WINDERMERE

6 Beds 9 Baths 8,305 SqFt Single Family Residence MLS® # O6230327
Active 9202 Bay Point Dr, ORLANDO

$5,950,000

▼ $549,000 BAY POINT

9202 Bay Point Dr, ORLANDO

5 Beds 7 Baths 8,844 SqFt Single Family Residence MLS® # T3542430
Active 5121 Latrobe Dr, WINDERMERE

$5,900,000

ISLEWORTH

5121 Latrobe Dr, WINDERMERE

6 Beds 7 Baths 8,178 SqFt Single Family Residence MLS® # O6249529
Active 1938 North Lakewood Ave, OCOEE

$5,899,000

1938 North Lakewood Ave, OCOEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6205884
Active 7625 Clarcona Ocoee Rd, ORLANDO

$5,699,999

▲ $1,704,999 NONE

7625 Clarcona Ocoee Rd, ORLANDO

2 Beds 2 Baths 6,610 SqFt Single Family Residence MLS® # O6174081
Active 210 Chelton Cir, WINTER PARK

$5,695,000

FOREST HILLS

210 Chelton Cir, WINTER PARK

5 Beds 6 Baths 5,264 SqFt Single Family Residence MLS® # O6239351
New
Active 11030 Bridge House Rd, WINDERMERE

$5,500,000

RESERVE AT LAKE BUTLER SOUND 45/120

11030 Bridge House Rd, WINDERMERE

7 Beds 9 Baths 8,107 SqFt Single Family Residence MLS® # O6272320

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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