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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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FEATURED
Active 2289 White Feather Loop, OAKLAND

$465,000

OAKLAND TRAILS

2289 White Feather Loop, OAKLAND

3 Beds 3 Baths 1,744 SqFt Single Family Residence MLS® # S5102598
FEATURED
Active 12539 Floridays Resort Drive 206-d, ORLANDO

$249,942

▼ $10,008 FLORIDAYS RESORT

12539 Floridays Resort Drive 206-d, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5098688
FEATURED
Active 8112 Poinciana Blvd 1712, ORLANDO

$225,000

LAKE BUENA VISTA RESORT

8112 Poinciana Blvd 1712, ORLANDO

3 Beds 2 Baths 1,231 SqFt Condo - Hotel MLS® # S5101858
New FEATURED
Active 8101 Resort Village Dr 31006, ORLANDO

$205,000

LAKE BUENA VISTA RESORT

8101 Resort Village Dr 31006, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5102738
FEATURED
Active 8000 Poinciana Blvd 2606, ORLANDO

$175,000

▼ $6,000 LAKE BUENA VISTA RESORT

8000 Poinciana Blvd 2606, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5096314
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 6004 Cartmel Ln, WINDERMERE

$30,000,000

RESERVE AT LAKE BUTLER SOUND

6004 Cartmel Ln, WINDERMERE

9 Beds 17 Baths 20,240 SqFt Single Family Residence MLS® # O6162188
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

GOLDEN OAK PHASE 3

10242 Summer Meadow Way, ORLANDO

7 Beds 10 Baths 9,254 SqFt Single Family Residence MLS® # O6101583
Active 9306 Blanche Cove Dr, WINDERMERE

$15,500,000

ISLEWORTH 7TH AMD

9306 Blanche Cove Dr, WINDERMERE

6 Beds 8 Baths 14,856 SqFt Single Family Residence MLS® # O6180696
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 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® # O6176943
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 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 7766 Wandering Way, ORLANDO

$9,300,000

PHILLIPS GROVE

7766 Wandering Way, ORLANDO

7 Beds 8 Baths 6,736 SqFt Single Family Residence MLS® # O6161203
Active Moss Park Rd, ORLANDO

$8,900,000

Moss Park Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5903841
Active 9725 Vista Falls Dr, GOLDEN OAK

$8,895,000

▼ $100,000 GOLDEN OAK PH 1C

9725 Vista Falls Dr, GOLDEN OAK

5 Beds 8 Baths 6,908 SqFt Single Family Residence MLS® # O6143067
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 11035 Schooner Way, WINDERMERE

$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 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 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 1001 Anchorage Ct, WINTER PARK

$7,250,000

CHAPMAN & CHASE PLAN/TOWN/WINT

1001 Anchorage Ct, WINTER PARK

5 Beds 7 Baths 9,075 SqFt Single Family Residence MLS® # O6156666
Active 6131 Grosvenor Shore Dr, WINDERMERE

$7,200,000

KEENES POINTE

6131 Grosvenor Shore Dr, WINDERMERE

7 Beds 9 Baths 8,596 SqFt Single Family Residence MLS® # O6189962
Active 1761 Pinetree Rd, WINTER PARK

$6,995,000

SICILIAN SHORES

1761 Pinetree Rd, WINTER PARK

5 Beds 6 Baths 4,792 SqFt Single Family Residence MLS® # O6195529
Active 6462 Deacon Cir, WINDERMERE

$6,950,000

ISLEWORTH

6462 Deacon Cir, WINDERMERE

5 Beds 6 Baths 7,178 SqFt Single Family Residence MLS® # O6173721
Active 14154 Ward Rd, ORLANDO

$6,500,000

LAKE PRESERVE

14154 Ward Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # S5102984
Active 5190 Latrobe Dr, WINDERMERE

$6,300,000

ISLEWORTH

5190 Latrobe Dr, WINDERMERE

5 Beds 8 Baths 7,191 SqFt Single Family Residence MLS® # O6172519
Active 5550 Osprey Isle Ln, ORLANDO

$6,195,000

▼ $200,000 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 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 10208 Morey Ct, ORLANDO

$5,800,000

GOLDEN OAKS

10208 Morey Ct, ORLANDO

4 Beds 6 Baths 4,315 SqFt Single Family Residence MLS® # O6168995
Active 526 Butler St, WINDERMERE

$5,755,000

WINDERMERE TOWN

526 Butler St, WINDERMERE

4 Beds 6 Baths 6,688 SqFt Single Family Residence MLS® # O6178229
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 2161 Sharon Rd, WINTER PARK

$5,566,500

▲ $28,000 TUSCANIA

2161 Sharon Rd, WINTER PARK

5 Beds 7 Baths 6,475 SqFt Single Family Residence MLS® # O6173028
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 6120 Kirkstone Ln, WINDERMERE

$5,400,000

▼ $799,000 RESERVE AT LAKE BUTLER SOUND

6120 Kirkstone Ln, WINDERMERE

5 Beds 7 Baths 6,972 SqFt Single Family Residence MLS® # O6172400
Active 2228 Azalea Pl, WINTER PARK

$5,400,000

MAITLAND SHORES FIRST ADD

2228 Azalea Pl, WINTER PARK

5 Beds 6 Baths 5,072 SqFt Single Family Residence MLS® # O6120809
Active 9205 Tibet Pointe Cir, WINDERMERE

$5,350,000

KEENES POINTE 46/104

9205 Tibet Pointe Cir, WINDERMERE

5 Beds 10 Baths 8,259 SqFt Single Family Residence MLS® # O6166914
Active 9844 Laurel Valley Dr, WINDERMERE

$5,300,000

ISLEWORTH

9844 Laurel Valley Dr, WINDERMERE

5 Beds 6 Baths 5,613 SqFt Single Family Residence MLS® # O6173216
Active 5745 Emerington Cres, ORLANDO

$5,140,000

EMERSON POINTE

5745 Emerington Cres, ORLANDO

7 Beds 8 Baths 7,881 SqFt Single Family Residence MLS® # O6184236
Active 6109 Orta Ct, WINDERMERE

$5,099,000

WATERSTONE

6109 Orta Ct, WINDERMERE

5 Beds 7 Baths 5,895 SqFt Single Family Residence MLS® # O6161019
Active 1110 Ivanhoe Blvd 32, ORLANDO

$5,000,000

▲ $5,000 RENAISSANCE AT LAKE IVANHOE CONDO

1110 Ivanhoe Blvd 32, ORLANDO

3 Beds 4 Baths 5,100 SqFt Condominium MLS® # O6132402
Active 6440 Canada Ave, ORLANDO

$5,000,000

▼ $1,000,000 INTERNATIONAL COVE

6440 Canada Ave, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5347857

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.

Browse Orange County Holiday Home Communities:

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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