#fc-orange-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!

Search Orange County Real Estate Listings

Sort by:
FEATURED
Active 4862 Cayview Ave 403, ORLANDO

$550,000

▼ $25,000 VISTA CAY

4862 Cayview Ave 403, ORLANDO

3 Beds 2 Baths 1,247 SqFt Residential Condominium MLS® # S5146137
FEATURED
Active 4816 Cayview Ave 201, ORLANDO

$525,000

VISTA CAY

4816 Cayview Ave 201, ORLANDO

2 Beds 2 Baths 1,823 SqFt Residential Condominium MLS® # S5146636
FEATURED
Active 4862 Cayview Ave 407, ORLANDO

$420,000

▼ $5,000 VISTA CAY

4862 Cayview Ave 407, ORLANDO

2 Beds 2 Baths 1,112 SqFt Residential Condominium MLS® # S5124892
FEATURED
Active 8774 Worldquest Blvd 7103, ORLANDO

$295,000

WORLDQUEST RESORT

8774 Worldquest Blvd 7103, ORLANDO

2 Beds 2 Baths 1,178 SqFt Residential Condo - Hotel MLS® # S5148952
FEATURED
Active 8801 Worldquest Blvd 4108, ORLANDO

$269,900

▼ $20,100 WORLDQUEST RESORT

8801 Worldquest Blvd 4108, ORLANDO

3 Beds 2 Baths 1,437 SqFt Residential Condo - Hotel MLS® # S5139165
FEATURED
Active 8100 Poinciana Blvd 2609, ORLANDO

$190,000

LAKE BUENA VISTA RESORT

8100 Poinciana Blvd 2609, ORLANDO

3 Beds 3 Baths 1,409 SqFt Residential Condo - Hotel MLS® # S5152135
FEATURED
Active 12538 Floridays Resort Drive 109c, ORLANDO

$190,000

FLORIDAYS RESORT

12538 Floridays Resort Drive 109c, ORLANDO

3 Beds 2 Baths 1,200 SqFt Residential Condo - Hotel MLS® # S5152010
FEATURED
Active 8112 Poinciana Blvd 1706, ORLANDO

$175,000

▼ $50,000 LAKE BUENA VISTA RESORT

8112 Poinciana Blvd 1706, ORLANDO

2 Beds 2 Baths 1,060 SqFt Residential Condo - Hotel MLS® # S5112618
FEATURED
Active 14501 Grove Resort Ave 1726, WINTER GARDEN

$174,999

THE GROVE RESORT AND SPA

14501 Grove Resort Ave 1726, WINTER GARDEN

2 Beds 2 Baths 1,265 SqFt Residential Condo - Hotel MLS® # S5151998
FEATURED
Active 12539 Floridays Resort Drive 305-d, ORLANDO

$165,000

▼ $5,000 FLORIDAYS RESORT

12539 Floridays Resort Drive 305-d, ORLANDO

2 Beds 2 Baths 957 SqFt Residential Condo - Hotel MLS® # S5105392
FEATURED
Active 7395 Universal Blvd 403, ORLANDO

$159,999

POINT ORLANDO RESORT

7395 Universal Blvd 403, ORLANDO

1 Bed 1 Bath 671 SqFt Residential Condo - Hotel MLS® # S5152062
FEATURED
Active 8100 Poinciana Blvd 2501, ORLANDO

$154,950

▼ $5,000 LAKE BUENA VISTA RESORT

8100 Poinciana Blvd 2501, ORLANDO

3 Beds 2 Baths 1,231 SqFt Residential Condo - Hotel MLS® # S5120932
FEATURED
Active 8101 Resort Village Dr 31314, ORLANDO

$149,999

▼ $20,000 LAKE BUENA VISTA RESORT

8101 Resort Village Dr 31314, ORLANDO

3 Beds 2 Baths 1,231 SqFt Residential Condo - Hotel MLS® # S5141827
FEATURED
Active 300 E South St 1003, ORLANDO

$139,998

▼ $1 GRANDE DOWNTOWN ORLANDO

300 E South St 1003, ORLANDO

1 Bed 1 Bath 744 SqFt Residential Condominium MLS® # S5149667
Active 9508 Windy Ridge Rd, WINDERMERE

$30,000,000

N/A

9508 Windy Ridge Rd, WINDERMERE

7 Beds 14 Baths 51,000 SqFt Residential Single Family Residence MLS® # O6411343
Active 5603 Marleon Dr, WINDERMERE

$27,000,000

NA

5603 Marleon Dr, WINDERMERE

7 Beds 10 Baths 22,108 SqFt Residential Single Family Residence MLS® # O6404938
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 Land MLS® # O6302395
New
Active 10084 Tavistock Rd, ORLANDO

$20,000,000

LAKE NONA ESTATES

10084 Tavistock Rd, ORLANDO

6 Beds 9 Baths 16,348 SqFt Residential Single Family Residence MLS® # O6409649
Active 11900 Lake Butler Blvd, WINDERMERE

$17,250,000

▼ $1,250,000 METCALF PARK REP

11900 Lake Butler Blvd, WINDERMERE

7 Beds 9 Baths 10,649 SqFt Residential 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 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 Land MLS® # A4668777
New
Active 6119 Grosvenor Shore Dr, WINDERMERE

$15,900,000

KEENE'S POINT

6119 Grosvenor Shore Dr, WINDERMERE

7 Beds 9 Baths 14,068 SqFt Residential Single Family Residence MLS® # O6421205
Active 10160 Autumn Mist Ln 800, GOLDEN OAK

$15,500,000

GOLDEN OAK FLORIAN PARK CONDOMINIUM

10160 Autumn Mist Ln 800, GOLDEN OAK

4 Beds 5 Baths 6,725 SqFt Residential Condominium MLS® # O6393339
Active 12488 Park Ave, WINDERMERE

$15,500,000

CHAINE DU LAC

12488 Park Ave, WINDERMERE

10 Beds 17 Baths 13,425 SqFt Residential Single Family Residence MLS® # O6395291
Active 3057 Porto Lago Ct, WINDERMERE

$13,995,000

LAKE DOWN POINTE 50 42

3057 Porto Lago Ct, WINDERMERE

6 Beds 11 Baths 12,067 SqFt Residential Single Family Residence MLS® # O6411245
Active 9832 Laurel Valley Dr, WINDERMERE

$13,900,000

ISLEWORTH

9832 Laurel Valley Dr, WINDERMERE

6 Beds 10 Baths 11,100 SqFt Residential Single Family Residence MLS® # O6416194
Active 7011 Via Carmel Way, ORLANDO

$13,500,000

▲ $1,500,000 CARMEL

7011 Via Carmel Way, ORLANDO

5 Beds 10 Baths 10,519 SqFt Residential Single Family Residence MLS® # O6320806
Active 9621 Windy Ridge Rd, WINDERMERE

$12,999,999

▼ $430,001 WINDSOR HILL

9621 Windy Ridge Rd, WINDERMERE

9 Beds 16 Baths 20,445 SqFt Residential Single Family Residence MLS® # O6400740
Active 570 Manor Rd, MAITLAND

$12,500,000

LAKE MAITLAND MANOR

570 Manor Rd, MAITLAND

6 Beds 10 Baths 11,668 SqFt Residential Single Family Residence MLS® # O6300040
Active 9312 Blanche Cove Dr, WINDERMERE

$12,350,000

ISLEWORTH 5TH AMD

9312 Blanche Cove Dr, WINDERMERE

7 Beds 10 Baths 11,465 SqFt Residential Single Family Residence MLS® # O6407102
Active 1955 S Apopka Vineland Rd, ORLANDO

$11,800,000

1955 S Apopka Vineland Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6211968
Active 9236 Bay Point Dr, ORLANDO

$11,490,000

▲ $90,000 BAY POINT

9236 Bay Point Dr, ORLANDO

5 Beds 10 Baths 9,757 SqFt Residential Single Family Residence MLS® # O6404671
Active 4226 Downeast Ln, WINDERMERE

$10,500,000

▼ $1,300,000 NA

4226 Downeast Ln, WINDERMERE

5 Beds 3 Baths 5,316 SqFt Residential Single Family Residence MLS® # O6355233
Active 4226 Downeast Ln, WINDERMERE

$10,500,000

▼ $1,300,000

4226 Downeast Ln, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6367852
Active 10160 Autumn Mist Ln 601, GOLDEN OAK

$10,500,000

▲ $250,000 GOLDEN OAK-FLORIAN PARK CONDOMINIUM

10160 Autumn Mist Ln 601, GOLDEN OAK

4 Beds 5 Baths 6,590 SqFt Residential Condominium MLS® # O6299022
Active 728 Forest St, WINDERMERE

$10,200,000

WINDERMERE TOWN

728 Forest St, WINDERMERE

6 Beds 9 Baths 6,457 SqFt Residential Single Family Residence MLS® # O6411906
Active 2584 W Kelly Park Rd, APOPKA

$10,000,000

2584 W Kelly Park Rd, APOPKA

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6238898
Active 9107 Sloane St, ORLANDO

$10,000,000

LAKE NONA ESTATES

9107 Sloane St, ORLANDO

5 Beds 7 Baths 8,300 SqFt Residential Single Family Residence MLS® # O6414998
Active 8506 Lake Nona Shore Dr, ORLANDO

$9,495,000

LAKE NONA ESTATES

8506 Lake Nona Shore Dr, ORLANDO

6 Beds 8 Baths 8,257 SqFt Residential Single Family Residence MLS® # O6392916
New
Active 10331 Winter Sparkle Cir, GOLDEN OAK

$8,995,000

GOLDEN OAK FLORIAN PARK

10331 Winter Sparkle Cir, GOLDEN OAK

5 Beds 6 Baths 4,742 SqFt Residential Condominium MLS® # O6421879
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 Residential Single Family Residence MLS® # O6350054
Active 12422 Park Ave, WINDERMERE

$8,695,000

CHAINE DU LAC

12422 Park Ave, WINDERMERE

0 Beds 0 Baths 0 SqFt Land Land MLS® # O6416090
Active 10300 Winter Sparkle Cir, GOLDEN OAK

$8,569,000

▲ $500,000 GOLDEN OAK FLORIAN PARK CONDOMINIUM

10300 Winter Sparkle Cir, GOLDEN OAK

4 Beds 5 Baths 4,836 SqFt Residential Condominium MLS® # O6276187
Active 13709 S Apopka Vineland Roads, ORLANDO

$8,500,000

LAKE BRYAN ESTATES

13709 S Apopka Vineland Roads, ORLANDO

0 Beds 0 Baths 0 SqFt Land Land MLS® # S5152176
New
Active 10335 Winter Sparkle Cir, GOLDEN OAK

$8,395,000

GOLDEN OAK FLORIAN PARK CONDOMINIUM

10335 Winter Sparkle Cir, GOLDEN OAK

4 Beds 5 Baths 4,592 SqFt Residential Condominium MLS® # O6421885
Active 9317 Gladys Garden Ct, WINDERMERE

$7,999,000

GARDENS/ISLEWORTH

9317 Gladys Garden Ct, WINDERMERE

6 Beds 9 Baths 8,038 SqFt Residential Single Family Residence MLS® # O6410843
Active 1530 Waterwitch Dr, ORLANDO

$7,900,000

TUXEDO ESTATES

1530 Waterwitch Dr, ORLANDO

5 Beds 7 Baths 5,769 SqFt Residential Single Family Residence MLS® # O6407557
Active 9343 Tibet Pointe Cir, WINDERMERE

$7,795,000

▼ $155,000 KEENES POINTE UNIT 03 46/104

9343 Tibet Pointe Cir, WINDERMERE

7 Beds 10 Baths 8,362 SqFt Residential Single Family Residence MLS® # O6264629

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!

^ Back to: Orange County Real Estate

Start searching for your dream home now.

When it comes to convenience, our site is unparalleled. Whether you're in the comfort of your home, or on the go.
Our site works flawlessly on multiple devices so you can find the information you need.

Start Search