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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 4862 Cayview Ave 407, ORLANDO

$449,950

VISTA CAY

4862 Cayview Ave 407, ORLANDO

2 Beds 2 Baths 1,112 SqFt Condominium MLS® # S5124892
FEATURED
Active 8601 Worldquest Blvd 3101, ORLANDO

$309,000

WORLDQUEST REOSRT

8601 Worldquest Blvd 3101, ORLANDO

3 Beds 2 Baths 1,437 SqFt Condo - Hotel MLS® # S5126362
FEATURED
Active 150 East Robinson St 219, ORLANDO

$299,950

▼ $35,000 THE VUE AT LAKE EOLA

150 East Robinson St 219, ORLANDO

1 Bed 2 Baths 925 SqFt Condominium MLS® # S5122537
FEATURED
Active 14501 Grove Resort Ave 3615, WINTER GARDEN

$299,000

GROVE RESORT

14501 Grove Resort Ave 3615, WINTER GARDEN

2 Beds 2 Baths 1,265 SqFt Condo - Hotel MLS® # S5123320
FEATURED
Active 8601 Worldquest Blvd 3502, ORLANDO

$289,950

WORLDQUEST RESORT

8601 Worldquest Blvd 3502, ORLANDO

3 Beds 2 Baths 1,421 SqFt Condo - Hotel MLS® # S5126365
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

$199,950

▼ $10,000 FLORIDAYS RESORT

12527 Floridays Resort Dr E-103, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5114808
FEATURED
Active 8101 Resort Village Drive B3/u3601, ORLANDO

$199,950

LAKE BUENA VISTA RESORT

8101 Resort Village Drive B3/u3601, ORLANDO

3 Beds 2 Baths 1,231 SqFt Condo - Hotel MLS® # S5119669
FEATURED
Active 8100 Poinciana Blvd 2501, ORLANDO

$190,950

▼ $3,000 LAKE BUENA VISTA RESORT

8100 Poinciana Blvd 2501, ORLANDO

3 Beds 2 Baths 1,231 SqFt Condo - Hotel MLS® # S5120932
FEATURED
Active 8100 Poinciana Boulevard B2/u2511, ORLANDO

$179,500

LAKE BUENA VISTA RESORT

8100 Poinciana Boulevard B2/u2511, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5119899
FEATURED
Active 8100 Poinciana Blvd 2703, ORLANDO

$172,000

LAKE BUENA VISTA RESORT

8100 Poinciana Blvd 2703, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5119192
FEATURED
Active 8101 Resort Village Dr 3712, ORLANDO

$169,000

▼ $10,900 LAKE BUENA VISTA RESORT

8101 Resort Village Dr 3712, ORLANDO

3 Beds 2 Baths 1,231 SqFt Condo - Hotel MLS® # S5121941
FEATURED
Active 1051 South Hiawassee Rd 2127, ORLANDO

$158,900

TRADEWINDS

1051 South Hiawassee Rd 2127, ORLANDO

2 Beds 2 Baths 934 SqFt Condominium MLS® # S5124459
FEATURED
Active 8100 Poinciana Blvd 2111, ORLANDO

$145,000

LAKE BUENA VISTA RESORT

8100 Poinciana Blvd 2111, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5123740
Active 4625-4651 West Kelly Park Rd, APOPKA

$25,000,000

4625-4651 West Kelly Park Rd, APOPKA

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

$20,000,000

METCALF PARK REP

11900 Lake Butler Blvd, WINDERMERE

7 Beds 9 Baths 10,649 SqFt Single Family Residence MLS® # O6275556
Active 9291 Point Cypress Dr, ORLANDO

$19,500,000

CYPRESS POINT PH 02

9291 Point Cypress Dr, ORLANDO

12 Beds 14 Baths 14,706 SqFt Single Family Residence MLS® # O6280213
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
New
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 10138 Enchanted Oak Dr, GOLDEN OAK

$13,000,000

GOLDEN OAK PH 1B

10138 Enchanted Oak Dr, GOLDEN OAK

5 Beds 7 Baths 7,001 SqFt Single Family Residence MLS® # O6295626
Active 570 Manor Rd, MAITLAND

$12,500,000

LAKE MAITLAND MANOR

570 Manor Rd, MAITLAND

6 Beds 10 Baths 11,668 SqFt Single Family Residence MLS® # O6300040
Active 1640 East Adams Dr, MAITLAND

$11,950,000

ADAMS GROVE

1640 East Adams Dr, MAITLAND

5 Beds 8 Baths 8,174 SqFt Single Family Residence MLS® # O6304588
Active 4200 Down Point Ln, WINDERMERE

$11,900,000

▼ $1,000,000 DOWN POINT SUB

4200 Down Point Ln, WINDERMERE

6 Beds 9 Baths 14,435 SqFt Single Family Residence MLS® # O6176070
Active 1120 Preserve Point Dr, WINTER PARK

$10,900,000

▼ $1,000,000 WINDSONG-PRESERVE POINT

1120 Preserve Point Dr, WINTER PARK

7 Beds 11 Baths 11,255 SqFt Single Family Residence MLS® # O6269585
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 10160 Autumn Mist Ln 601, GOLDEN OAK

$9,900,000

GOLDEN OAK-FLORIAN PARK CONDOMINIUM

10160 Autumn Mist Ln 601, GOLDEN OAK

4 Beds 5 Baths 7,015 SqFt Condominium MLS® # O6299022
Active 17017 Marsh Rd, WINTER GARDEN

$9,900,000

▼ $2,100,000 NONE

17017 Marsh Rd, WINTER GARDEN

6 Beds 6 Baths 6,977 SqFt Single Family Residence MLS® # O6254855
Active 6137 Grosvenor Shore Dr, WINDERMERE

$9,500,000

▼ $495,000 KEENE'S POINTE

6137 Grosvenor Shore Dr, WINDERMERE

6 Beds 9 Baths 9,571 SqFt Single Family Residence MLS® # O6294487
Active 9832 Laurel Valley Dr, WINDERMERE

$9,490,000

▼ $410,000 ISLEWORTH

9832 Laurel Valley Dr, WINDERMERE

6 Beds 10 Baths 11,100 SqFt Single Family Residence MLS® # O6211352
Active 6139 Greatwater Dr, WINDERMERE

$9,218,000

KEENES POINTE UNIT 01

6139 Greatwater Dr, WINDERMERE

5 Beds 7 Baths 8,914 SqFt Single Family Residence MLS® # O6306210
Active Moss Park Rd, ORLANDO

$8,900,000

Moss Park Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5903841
Active 2661 Via Tuscany, WINTER PARK

$8,799,000

▼ $2,200,999 WINTER PARK

2661 Via Tuscany, WINTER PARK

4 Beds 5 Baths 4,564 SqFt Single Family Residence MLS® # O6260493
Active 5271 Isleworth Country Club Dr, WINDERMERE

$8,775,000

ISLEWORTH

5271 Isleworth Country Club Dr, WINDERMERE

7 Beds 13 Baths 11,403 SqFt Single Family Residence MLS® # O6267644
Active 9343 Tibet Pointe Cir, WINDERMERE

$8,490,000

▼ $300,000 KEENES POINTE UNIT 03 46/104

9343 Tibet Pointe Cir, WINDERMERE

7 Beds 10 Baths 8,362 SqFt Single Family Residence MLS® # O6264629
Active 9122 Bay Point Dr, ORLANDO

$7,995,000

BAY POINT

9122 Bay Point Dr, ORLANDO

4 Beds 6 Baths 5,654 SqFt Single Family Residence MLS® # O6273889
Active 9726 Kilgore Rd, ORLANDO

$7,900,000

▼ $2,000,000 N/A

9726 Kilgore Rd, ORLANDO

4 Beds 6 Baths 10,010 SqFt Single Family Residence MLS® # O6229408
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 10300 Winter Sparkle Cir, GOLDEN OAK

$7,770,000

▲ $250,000 GOLDEN OAK FLORIAN PARK CONDOMINIUM

10300 Winter Sparkle Cir, GOLDEN OAK

4 Beds 5 Baths 4,836 SqFt Condominium MLS® # O6276187
Active 6126 Kirkstone Ln, WINDERMERE

$7,500,000

▼ $150,000 RESERVE AT LAKE BUTLER SOUND 45/120

6126 Kirkstone Ln, WINDERMERE

5 Beds 7 Baths 8,691 SqFt Single Family Residence MLS® # O6278696
Active 11103 Bridge House Rd, WINDERMERE

$7,500,000

▼ $1,700,000 RESERVE AT LAKE BUTLER SOUND 45/120

11103 Bridge House Rd, WINDERMERE

5 Beds 8 Baths 9,403 SqFt Single Family Residence MLS® # O6266876
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 5507 Worsham Ct, WINDERMERE

$7,500,000

▼ $350,000 ISLEWORTH

5507 Worsham Ct, WINDERMERE

5 Beds 11 Baths 10,200 SqFt Single Family Residence MLS® # O6180706
Active 2725 Rayburn St, ORLANDO

$7,400,000

▼ $200,000 PROSPER COLONY 06-24-30

2725 Rayburn St, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6275444
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 1400 Alabama Dr, WINTER PARK

$6,500,000

▼ $450,000 J KRONENBERGER SUB

1400 Alabama Dr, WINTER PARK

5 Beds 9 Baths 7,916 SqFt Single Family Residence MLS® # O6285791

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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