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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 7417 Lake Albert Dr, WINDERMERE

$1,690,000

LAKE BURDEN

7417 Lake Albert Dr, WINDERMERE

6 Beds 7 Baths 5,006 SqFt Single Family Residence MLS® # S5135158
FEATURED
Active 4862 Cayview Ave 407, ORLANDO

$425,000

▼ $9,999 VISTA CAY

4862 Cayview Ave 407, ORLANDO

2 Beds 2 Baths 1,112 SqFt Condominium MLS® # S5124892
FEATURED
Active 8774 Worldquest Blvd 7307, ORLANDO

$324,999

WORLDQUEST RESORT

8774 Worldquest Blvd 7307, ORLANDO

3 Beds 2 Baths 1,421 SqFt Condo - Hotel MLS® # S5137664
FEATURED
Active 8801 Worldquest Blvd 4108, ORLANDO

$290,000

WORLDQUEST RESORT

8801 Worldquest Blvd 4108, ORLANDO

3 Beds 2 Baths 1,437 SqFt Condo - Hotel MLS® # S5139165
FEATURED
Active 8774 Worldquest Blvd 7404, ORLANDO

$289,999

▼ $5,000 WORLDQUEST RESORT

8774 Worldquest Blvd 7404, ORLANDO

3 Beds 3 Baths 1,459 SqFt Condo - Hotel MLS® # S5130693
FEATURED
Active 14501 Grove Resort Ave 3215, WINTER GARDEN

$259,000

GROVE RESORT

14501 Grove Resort Ave 3215, WINTER GARDEN

2 Beds 2 Baths 1,265 SqFt Condo - Hotel MLS® # S5138120
FEATURED
Active 14501 Grove Resort Ave 3615, WINTER GARDEN

$259,000

▼ $20,000 GROVE RESORT

14501 Grove Resort Ave 3615, WINTER GARDEN

2 Beds 2 Baths 1,265 SqFt Condo - Hotel MLS® # S5123320
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 12539 Floridays Resort Drive 305-d, ORLANDO

$215,000

FLORIDAYS RESORT

12539 Floridays Resort Drive 305-d, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5105392
FEATURED
Active 8100 Poinciana Boulevard B2/u2511, ORLANDO

$159,500

▼ $20,000 LAKE BUENA VISTA RESORT

8100 Poinciana Boulevard B2/u2511, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5119899
FEATURED
Active 6172 Peregrine Ave, ORLANDO

$145,000

▼ $4,900 WINDHOVER

6172 Peregrine Ave, ORLANDO

1 Bed 1 Bath 591 SqFt Condominium MLS® # S5134563
FEATURED
Active 1051 S Hiawassee Rd 2127, ORLANDO

$143,900

▼ $15,000 TRADEWINDS

1051 S Hiawassee Rd 2127, ORLANDO

2 Beds 2 Baths 934 SqFt Condominium MLS® # S5124459
Active 4625-4651 W Kelly Park Rd, APOPKA

$25,000,000

4625-4651 W Kelly Park Rd, APOPKA

0 Beds 0 Baths 0 SqFt Land MLS® # O6302395
Active 11900 Lake Butler Blvd, WINDERMERE

$18,500,000

METCALF PARK REP

11900 Lake Butler Blvd, WINDERMERE

7 Beds 9 Baths 10,649 SqFt Single Family Residence MLS® # O6275556
Active 17802 Old Ymca Rd, WINTER GARDEN

$16,000,000

17802 Old Ymca Rd, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land MLS® # O5968921
Active 11990 International Dr, ORLANDO

$16,000,000

ORANGEWOOD NEIGHBORHOOD-2

11990 International Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # A4668777
Active 4226 Downeast Ln, WINDERMERE

$14,800,000

NA

4226 Downeast Ln, WINDERMERE

5 Beds 3 Baths 5,316 SqFt Single Family Residence MLS® # O6355233
Active 5525 Isleworth Country Club Dr, WINDERMERE

$14,250,000

ISLEWORTH

5525 Isleworth Country Club Dr, WINDERMERE

5 Beds 6 Baths 9,511 SqFt Single Family Residence MLS® # O6304800
Active 10151 Enchanted Oak Dr, GOLDEN OAK

$13,995,000

▼ $505,000 GOLDEN OAK PH 1C

10151 Enchanted Oak Dr, GOLDEN OAK

7 Beds 9 Baths 10,740 SqFt Single Family Residence MLS® # O6344365
Active 9621 Windy Ridge Rd, WINDERMERE

$13,650,000

▼ $50,000 WINDSOR HILL

9621 Windy Ridge Rd, WINDERMERE

9 Beds 16 Baths 20,445 SqFt Single Family Residence MLS® # O6333091
Active 10065 Autumn Mist Ln, GOLDEN OAK

$13,500,000

GOLDEN OAK PH 3

10065 Autumn Mist Ln, GOLDEN OAK

5 Beds 8 Baths 6,872 SqFt Single Family Residence MLS® # O6339148
Active 10273 Summer Meadow Way, GOLDEN OAK

$12,750,000

GOLDEN OAK PH 3

10273 Summer Meadow Way, GOLDEN OAK

6 Beds 9 Baths 7,177 SqFt Single Family Residence MLS® # O6364828
Active 7011 Via Carmel Way, ORLANDO

$12,000,000

▲ $1,500,000 CARMEL

7011 Via Carmel Way, ORLANDO

5 Beds 10 Baths 10,519 SqFt Single Family Residence MLS® # O6320806
Active 10012 Hyperion Ln, GOLDEN OAK

$11,000,000

GOLDEN OAK PH 4

10012 Hyperion Ln, GOLDEN OAK

5 Beds 7 Baths 6,276 SqFt Single Family Residence MLS® # O6363272
Active 1640 E Adams Dr, MAITLAND

$10,950,000

▼ $1,000,000 ADAMS GROVE

1640 E Adams Dr, MAITLAND

5 Beds 8 Baths 8,174 SqFt Single Family Residence MLS® # O6304588
Active 10160 Autumn Mist Ln 601, GOLDEN OAK

$10,250,000

▲ $250,010 GOLDEN OAK-FLORIAN PARK CONDOMINIUM

10160 Autumn Mist Ln 601, GOLDEN OAK

4 Beds 5 Baths 7,015 SqFt Condominium MLS® # O6299022
Active 4212 Hogshead Rd, APOPKA

$10,000,000

4212 Hogshead Rd, APOPKA

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

$10,000,000

2584 W Kelly Park Rd, APOPKA

0 Beds 0 Baths 0 SqFt Land MLS® # O6238898
Active 6149 Grosvenor Shore Dr, WINDERMERE

$9,999,000

KEENES POINTE

6149 Grosvenor Shore Dr, WINDERMERE

6 Beds 8 Baths 6,783 SqFt Single Family Residence MLS® # O6356355
Active 6137 Grosvenor Shore Dr, WINDERMERE

$8,995,000

▼ $505,000 KEENES POINTE

6137 Grosvenor Shore Dr, WINDERMERE

6 Beds 9 Baths 9,571 SqFt Single Family Residence MLS® # O6294487
Active 1120 Preserve Point Dr, WINTER PARK

$8,950,000

WINDSONG-PRESERVE POINT

1120 Preserve Point Dr, WINTER PARK

7 Beds 11 Baths 11,255 SqFt Single Family Residence MLS® # O6350054
Active Moss Park Rd, ORLANDO

$8,900,000

Moss Park Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5903841
Active 1112 Preserve Point Dr, WINTER PARK

$8,500,000

WINDSONG PRESERVE POINT 43/76

1112 Preserve Point Dr, WINTER PARK

5 Beds 6 Baths 6,502 SqFt Single Family Residence MLS® # O6312768
Active 9343 Tibet Pointe Cir, WINDERMERE

$8,250,000

▼ $239,000 KEENES POINTE UNIT 03 46/104

9343 Tibet Pointe Cir, WINDERMERE

7 Beds 10 Baths 8,362 SqFt Single Family Residence MLS® # O6264629
Active 4170 & 4150 S Goldenrod Rd, ORLANDO

$8,100,000

LOS TERRANOS

4170 & 4150 S Goldenrod Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6348739
Active 10300 Winter Sparkle Cir, GOLDEN OAK

$8,069,000

▲ $120,000 GOLDEN OAK FLORIAN PARK CONDOMINIUM

10300 Winter Sparkle Cir, GOLDEN OAK

4 Beds 5 Baths 4,836 SqFt Condominium MLS® # O6276187
Active 9726 Kilgore Rd, ORLANDO

$7,900,000

N/A

9726 Kilgore Rd, ORLANDO

5 Beds 6 Baths 10,010 SqFt Single Family Residence MLS® # O6339007
Active 6507 Rosella Ct, WINDERMERE

$7,750,000

KEENES POINTE 46/104

6507 Rosella Ct, WINDERMERE

7 Beds 8 Baths 10,485 SqFt Single Family Residence MLS® # O6353035
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 8774 Lake Tibet Ct, ORLANDO

$7,500,000

CYPRESS POINT

8774 Lake Tibet Ct, ORLANDO

5 Beds 8 Baths 7,043 SqFt Single Family Residence MLS® # O6353160
Active 9564 Kilgore Rd, ORLANDO

$7,500,000

NA

9564 Kilgore Rd, ORLANDO

6 Beds 8 Baths 7,313 SqFt Single Family Residence MLS® # O6338462
Active 550 Palmer Ave, WINTER PARK

$7,200,000

OSCEOLA PLACE

550 Palmer Ave, WINTER PARK

5 Beds 7 Baths 5,939 SqFt Single Family Residence MLS® # O6349188
Active 9259 Tibet Pointe Cir, WINDERMERE

$6,800,000

KEENES POINTE

9259 Tibet Pointe Cir, WINDERMERE

5 Beds 6 Baths 6,257 SqFt Single Family Residence MLS® # O6312645
Active 11103 Bridge House Rd, WINDERMERE

$6,799,000

▼ $451,000 RESERVE AT LAKE BUTLER SOUND 45/120

11103 Bridge House Rd, WINDERMERE

5 Beds 8 Baths 8,443 SqFt Single Family Residence MLS® # O6315165
Active 9700 Blandford Rd, ORLANDO

$6,750,000

▲ $792,000 LAKE NONA ESTATES

9700 Blandford Rd, ORLANDO

5 Beds 7 Baths 6,732 SqFt Single Family Residence MLS® # O6332582
Active 2661 Via Tuscany, WINTER PARK

$6,600,000

▼ $1,900,000 WINTER PARK

2661 Via Tuscany, WINTER PARK

4 Beds 5 Baths 4,636 SqFt Single Family Residence MLS® # O6260493
Active 9639 Westover Roberts Rd, WINDERMERE

$6,395,000

GOTHA TOWN

9639 Westover Roberts Rd, WINDERMERE

5 Beds 9 Baths 11,861 SqFt Single Family Residence MLS® # O6341883
Active 10224 Mattraw Pl, ORLANDO

$6,250,000

▼ $245,000 GOLDEN OAK PH 2B & 2C

10224 Mattraw Pl, ORLANDO

5 Beds 5 Baths 3,753 SqFt Single Family Residence MLS® # O6332301

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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