County: Orange County | Osceola County | Polk County | Lake County

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

$375,000

BLUE HERON BEACH RESORT

13427 Blue Heron Beach Dr 303, ORLANDO

2 Beds 2 Baths 1,165 SqFt Condo - Hotel MLS® # S5091415

FEATURED

Active

$249,000

▼ $10,950 FLORIDAYS

12521 Floridays Resort Drive 505-f, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5086964

FEATURED

Active

$199,950

▼ $10,000 LAKE BUENA VISTA RESORT VILLAGE

8000 Poinciana Blvd 2512, ORLANDO

3 Beds 2 Baths 1,231 SqFt Condo - Hotel MLS® # S5088160

FEATURED

Active

$104,995

▼ $5 PARC CORNICHE

6402 Parc Corniche Dr 5309, ORLANDO

1 Bed 1 Bath 550 SqFt Condominium MLS® # S5089488

Active

$30,000,000

ACREAGE & UNREC

9508 Windy Ridge Rd, WINDERMERE

7 Beds 16 Baths 29,739 SqFt Single Family Residence MLS® # U8207115

Active

$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

$19,000,000

GOLDEN OAK PHASE 3

10242 Summer Meadow Way, ORLANDO

7 Beds 10 Baths 9,254 SqFt Single Family Residence MLS® # O6101583

Active

$18,000,000

SHOPPERS WORLD

6447 Grand National Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6096620

Active

$17,486,000

▲ $1,500,000 TWELVE OAKS

1220 North Park Ave, WINTER PARK

7 Beds 7 Baths 12,475 SqFt Single Family Residence MLS® # O6012672

Active

$16,500,000

▼ $1,000,000 ISLEWORTH

9306 Blanche Cove Dr, WINDERMERE

5 Beds 8 Baths 14,856 SqFt Single Family Residence MLS® # O6097686

Active

$16,000,000

CLOISTER GROVE SUB

1461 Via Tuscany, WINTER PARK

5 Beds 6 Baths 8,353 SqFt Single Family Residence MLS® # O6112070

Active

$13,800,000

GOLDEN OAK PH 1C

10151 Enchanted Oak Dr, GOLDEN OAK

7 Beds 9 Baths 10,742 SqFt Single Family Residence MLS® # O6143312

Active

$12,888,000

▼ $2,112,000 BENTLEY PARK 2ND REP

9200 Bentley Park Cir, ORLANDO

7 Beds 12 Baths 20,690 SqFt Single Family Residence MLS® # L4930944

Active

$11,995,000

GOLDEN OAK PH 3

10297 Summer Meadow Way, GOLDEN OAK

5 Beds 7 Baths 6,756 SqFt Single Family Residence MLS® # O6118207

Active

$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

$10,950,000

ISLE OF SICILY

4 Isle Of Sicily, WINTER PARK

5 Beds 8 Baths 9,522 SqFt Single Family Residence MLS® # O6095179

New

Active

$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

$9,500,000

17802 Old Ymca Rd, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land MLS® # O5968921

Active

$8,995,000

GOLDEN OAK PH 1C

9725 Vista Falls Dr, GOLDEN OAK

5 Beds 8 Baths 6,908 SqFt Single Family Residence MLS® # O6143067

Active

$8,975,000

ISLEWORTH

5200 Isleworth Country Club Dr, WINDERMERE

5 Beds 8 Baths 9,482 SqFt Single Family Residence MLS® # O6124594

Active

$8,900,000

Moss Park Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5903841

Active

$8,300,000

ISLEWORTH

6432 Deacon Cir, WINDERMERE

5 Beds 9 Baths 11,021 SqFt Single Family Residence MLS® # O6120407

Active

$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

$8,112,500

WILLIS R MUNGERS LAND SUB

International Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5557835

Active

$7,900,000

▼ $590,000 RESERVE AT LAKE BUTLER SOUND

6120 Kirkstone Ln, WINDERMERE

6 Beds 8 Baths 6,972 SqFt Single Family Residence MLS® # O6131593

Active

$7,600,000

MORSE & PENNSYLVANIA TWNHMS

654 West Morse Blvd, WINTER PARK

5 Beds 8 Baths 8,752 SqFt Single Family Residence MLS® # O6133999

Active

$7,440,000

LAKE DOWN ESTATES

10988 Down Park Ln, WINDERMERE

4 Beds 6 Baths 8,446 SqFt Single Family Residence MLS® # O6021133

Active

$7,250,000

RESERVE AT LAKE BUTLER SOUND

11019 Bridge House Road R, WINDERMERE

7 Beds 11 Baths 9,376 SqFt Single Family Residence MLS® # O6115064

Active

$7,150,000

▼ $250,000 KEENES POINTE

6125 Grosvenor Shore Dr, WINDERMERE

6 Beds 7 Baths 8,287 SqFt Single Family Residence MLS® # O6103885

Active

$7,000,000

ACREAGE & UNREC

9520 Windy Ridge Rd, windermere, Fl Rd, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # U8211301

Active

$6,950,000

▼ $2,350,000 LAKE NONA ESTATES

9086 Mayfair Pointe Dr, ORLANDO

5 Beds 10 Baths 8,245 SqFt Single Family Residence MLS® # O6109126

Active

$6,500,000

KEENES POINTE 46/104

9139 Tibet Pointe Cir, WINDERMERE

6 Beds 9 Baths 10,341 SqFt Single Family Residence MLS® # O6080288

Active

$6,475,000

▼ $20,000 ISLE OF OSPREY

5550 Osprey Isle Ln, ORLANDO

5 Beds 6 Baths 6,730 SqFt Single Family Residence MLS® # O6115072

Active

$6,450,000

ISLEWORTH 01 AMD

5518 Worsham Ct, WINDERMERE

5 Beds 8 Baths 8,100 SqFt Single Family Residence MLS® # O6141598

Active

$6,300,000

▼ $1,600,000 RESERVE AT LAKE BUTLER SOUND 45/120

11205 Bridge House Rd, WINDERMERE

6 Beds 8 Baths 8,330 SqFt Single Family Residence MLS® # O6088503

Active

$6,000,000

INTERNATIONAL COVE

6440 Canada Ave, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5347857

Active

$5,997,000

NONE

13377 Lake Butler Blvd, WINTER GARDEN

5 Beds 5 Baths 6,210 SqFt Single Family Residence MLS® # O6100391

New

Active

$5,975,000

ISLEWORTH

5174 Vardon Dr, WINDERMERE

6 Beds 9 Baths 10,701 SqFt Single Family Residence MLS® # O6143716

Active

$5,950,000

▼ $250,000 CHAINE DU LAC

12632 Park Ave, WINDERMERE

6 Beds 9 Baths 10,213 SqFt Single Family Residence MLS® # O6123105

Active

$5,950,000

▼ $500,000 EMERSON POINTE

5619 Emerson Pointe Way, ORLANDO

4 Beds 7 Baths 7,602 SqFt Single Family Residence MLS® # O6119048

Active

$5,800,000

RESERVE AT LAKE BUTLER SOUND 45/120

11217 Bridge House Rd, WINDERMERE

6 Beds 8 Baths 6,755 SqFt Single Family Residence MLS® # O6136367

Active

$5,520,400

2061 West Kelly Park Rd, APOPKA

0 Beds 0 Baths 0 SqFt Land MLS® # G5069406

Active

$5,520,400

2045 West Kelly Park Rd, APOPKA

0 Beds 0 Baths 0 SqFt Land MLS® # G5069404

Active

$5,500,000

LAKE DOWN ESTATES

10908 Down Yonder Ln, WINDERMERE

6 Beds 7 Baths 5,305 SqFt Single Family Residence MLS® # O6102219

Active

$5,495,000

LAKE NONA ESTATES

9580 Sloane St, ORLANDO

5 Beds 6 Baths 8,263 SqFt Single Family Residence MLS® # O6133244

Active

$5,450,000

▲ $500,000 CHAINE DU LAC

12422 Park Ave, WINDERMERE

0 Beds 0 Baths 0 SqFt Land MLS® # O5967251

Active

$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

$5,250,000

NONE

13395 Kirby Smith Rd, ORLANDO

4 Beds 5 Baths 7,058 SqFt Single Family Residence MLS® # O6128450

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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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