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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 12544 Floridays Resort Drive 506-b, ORLANDO

$265,000

FLORIDAYS RESORT

12544 Floridays Resort Drive 506-b, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5105523
FEATURED
Active 12556 Floridays Resort Drive 304-a, ORLANDO

$263,950

▼ $5,050 FLORIDAYS RESORT

12556 Floridays Resort Drive 304-a, ORLANDO

3 Beds 2 Baths 1,200 SqFt Condo - Hotel MLS® # S5105047
FEATURED
Active 12521 Floridays Resort Drive 404-f, ORLANDO

$258,950

FLORIDAYS RESORT

12521 Floridays Resort Drive 404-f, ORLANDO

3 Beds 2 Baths 1,200 SqFt Condo - Hotel MLS® # S5107545
FEATURED
Active 13415 Blue Heron Beach Dr 103, ORLANDO

$249,900

▼ $10,000 BLUE HERON BEACH RESORT

13415 Blue Heron Beach Dr 103, ORLANDO

1 Bed 2 Baths 798 SqFt Condo - Hotel MLS® # S5106710
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 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 7601 Canada Ave 305, ORLANDO

$118,000

▼ $6,000 STAYSKY SUITES, HAWTHORN SUITES

7601 Canada Ave 305, ORLANDO

1 Bed 1 Bath 542 SqFt Condo - Hotel MLS® # S5098440
Active 11900 & 11910 Lake Butler Lake Butler Blvd, WINDERMERE

$22,000,000

METCALF PARK REP

11900 & 11910 Lake Butler Lake Butler Blvd, WINDERMERE

6 Beds 6 Baths 11,253 SqFt Single Family Residence MLS® # O6197372
Active 9291 Point Cypress Dr, ORLANDO

$19,500,000

▼ $5,500,000 CYPRESS POINT PH 02

9291 Point Cypress Dr, ORLANDO

12 Beds 15 Baths 14,706 SqFt Single Family Residence MLS® # O5965014
Active 6447 Grand National Dr, ORLANDO

$18,000,000

SHOPPERS WORLD

6447 Grand National Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6096620
Active 10242 Summer Meadow Way, ORLANDO

$17,500,000

▼ $1,500,000 GOLDEN OAK PHASE 3

10242 Summer Meadow Way, ORLANDO

7 Beds 10 Baths 9,254 SqFt Single Family Residence MLS® # O6101583
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 9621 Windy Ridge Rd, WINDERMERE

$13,950,000

WINDSOR HILL

9621 Windy Ridge Rd, WINDERMERE

9 Beds 16 Baths 20,445 SqFt Single Family Residence MLS® # O6184943
Active 4200 Down Point Ln, WINDERMERE

$13,900,000

DOWN POINT SUB

4200 Down Point Ln, WINDERMERE

6 Beds 9 Baths 14,435 SqFt Single Family Residence MLS® # O6176070
Active 9832 Laurel Valley Dr, WINDERMERE

$13,250,000

ISLEWORTH

9832 Laurel Valley Dr, WINDERMERE

6 Beds 10 Baths 11,100 SqFt Single Family Residence MLS® # O6211352
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 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 181 Virginia Dr, WINTER PARK

$11,795,000

ELLNO WILLO

181 Virginia Dr, WINTER PARK

5 Beds 8 Baths 8,188 SqFt Single Family Residence MLS® # O6199109
Active 10254 Summer Meadow Way, ORLANDO

$9,999,950

GOLDEN OAK PH 3

10254 Summer Meadow Way, ORLANDO

5 Beds 7 Baths 6,396 SqFt Single Family Residence MLS® # O6139692
Active Moss Park Rd, ORLANDO

$8,900,000

Moss Park Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5903841
Active 9714 Vista Falls Dr, GOLDEN OAK

$8,699,000

▼ $300,000 GOLDEN OAK PH 01B

9714 Vista Falls Dr, GOLDEN OAK

6 Beds 10 Baths 6,793 SqFt Single Family Residence MLS® # O6182198
Active 5507 Worsham Ct, WINDERMERE

$8,650,000

ISLEWORTH

5507 Worsham Ct, WINDERMERE

5 Beds 11 Baths 10,200 SqFt Single Family Residence MLS® # O6180706
Active 7766 Wandering Way, ORLANDO

$8,100,000

▼ $1,200,000 PHILLIPS GROVE

7766 Wandering Way, ORLANDO

7 Beds 8 Baths 6,736 SqFt Single Family Residence MLS® # O6161203
Active 9313 Tibet Pointe Cir, WINDERMERE

$7,999,000

KEENES POINTE 46/104

9313 Tibet Pointe Cir, WINDERMERE

6 Beds 8 Baths 8,792 SqFt Single Family Residence MLS® # O6170422
Active 10424 Pocket Ln, ORLANDO

$7,895,000

WILLIS R MUNGERS LAND SUB

10424 Pocket Ln, ORLANDO

5 Beds 7 Baths 5,800 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 1400 Alabama Dr, WINTER PARK

$7,500,000

▼ $499,999 J KRONENBERGER SUB

1400 Alabama Dr, WINTER PARK

5 Beds 9 Baths 7,916 SqFt Single Family Residence MLS® # O6212012
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 1210 Via Capri, WINTER PARK

$7,370,000

CLOISTER GROVE SUB

1210 Via Capri, WINTER PARK

6 Beds 7 Baths 6,774 SqFt Single Family Residence MLS® # O6183317
Active 500 North Interlachen Ave, WINTER PARK

$7,250,000

WINTER PARK

500 North Interlachen Ave, WINTER PARK

4 Beds 5 Baths 4,581 SqFt Single Family Residence MLS® # O6206309
New
Active 9202 Bay Point Dr, ORLANDO

$7,000,000

BAY POINT

9202 Bay Point Dr, ORLANDO

5 Beds 7 Baths 8,844 SqFt Single Family Residence MLS® # T3542430
Active 119 Whitecaps Cir, MAITLAND

$6,500,000

HOLLIEANNA SHORES 1ST ADD

119 Whitecaps Cir, MAITLAND

5 Beds 6 Baths 6,441 SqFt Single Family Residence MLS® # O6215491
Active 14154 Ward Rd, ORLANDO

$6,500,000

LAKE PRESERVE

14154 Ward Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # S5102984
Active 5550 Osprey Isle Ln, ORLANDO

$5,999,500

▼ $195,500 ISLE OF OSPREY

5550 Osprey Isle Ln, ORLANDO

5 Beds 6 Baths 6,730 SqFt Single Family Residence MLS® # O6115072
Active 13377 Lake Butler Blvd, WINTER GARDEN

$5,997,000

NONE

13377 Lake Butler Blvd, WINTER GARDEN

5 Beds 5 Baths 6,210 SqFt Single Family Residence MLS® # O6100391
Active 1761 Pinetree Rd, WINTER PARK

$5,995,000

▼ $200,000 SICILIAN SHORES

1761 Pinetree Rd, WINTER PARK

5 Beds 6 Baths 4,792 SqFt Single Family Residence MLS® # O6195529
Active 9139 Tibet Pointe Cir, WINDERMERE

$5,995,000

▼ $500,000 KEENES POINTE 46/104

9139 Tibet Pointe Cir, WINDERMERE

6 Beds 9 Baths 10,341 SqFt Single Family Residence MLS® # O6163962
Active 10821 Bayshore Dr, WINDERMERE

$5,950,000

BAYSHORE ESTATES

10821 Bayshore Dr, WINDERMERE

4 Beds 6 Baths 5,275 SqFt Single Family Residence MLS® # O6189960
Active 11449 Waterstone Loop Dr, WINDERMERE

$5,950,000

▼ $550,000 WATERSTONE

11449 Waterstone Loop Dr, WINDERMERE

6 Beds 6 Baths 6,235 SqFt Single Family Residence MLS® # O6170332
Active 10716 Golden Cypress Ct, ORLANDO

$5,900,000

WILLIS R MUNGERS LAND SUB

10716 Golden Cypress Ct, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6211532
Active 1938 North Lakewood Ave, OCOEE

$5,899,000

1938 North Lakewood Ave, OCOEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6205884
Active 12540 Park Ave, WINDERMERE

$5,750,000

▼ $50,000 CHAINE DE LAC

12540 Park Ave, WINDERMERE

5 Beds 7 Baths 7,736 SqFt Single Family Residence MLS® # O6151810
Active 11618 Vinci Dr, WINDERMERE

$5,700,000

▼ $300,000 KEENES POINTE

11618 Vinci Dr, WINDERMERE

5 Beds 7 Baths 5,260 SqFt Single Family Residence MLS® # O6201378
Active 698 North New York Ave, WINTER PARK

$5,695,000

GREENS/PK

698 North New York Ave, WINTER PARK

4 Beds 5 Baths 5,096 SqFt Single Family Residence MLS® # O6211406
Active 10074 Symphony Grove Dr, GOLDEN OAK

$5,599,900

GOLDEN OAK PH 5

10074 Symphony Grove Dr, GOLDEN OAK

4 Beds 5 Baths 3,208 SqFt Single Family Residence MLS® # O6211509
Active 5174 Vardon Dr, WINDERMERE

$5,500,000

▼ $475,000 ISLEWORTH

5174 Vardon Dr, WINDERMERE

6 Beds 9 Baths 10,701 SqFt Single Family Residence MLS® # O6143716
Active 2161 Sharon Rd, WINTER PARK

$5,459,739

▼ $73,594 TUSCANIA

2161 Sharon Rd, WINTER PARK

5 Beds 7 Baths 6,475 SqFt Single Family Residence MLS® # O6173028
Active 1009 Down Reserve Ct, WINDERMERE

$5,395,000

ROSSER RESERVE REP

1009 Down Reserve Ct, WINDERMERE

5 Beds 8 Baths 7,940 SqFt Single Family Residence MLS® # O6202499

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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