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!
Search Orange County Real Estate Listings
Active
$25,000,000
CYPRESS POINT PH 02
9291 Point Cypress Dr, ORLANDO
12
Beds
15
Baths
14,706 SqFt
Single Family Residence
MLS® # O5965014
Active
$24,995,000
▼ $5,005,000
ACREAGE & UNREC
9508 Windy Ridge Rd, WINDERMERE
7
Beds
16
Baths
29,739 SqFt
Single Family Residence
MLS® # O6060999
Active
$23,300,000
▲ $5,300,000
GOODWINS ADD
110 West Jefferson St, ORLANDO
0
Beds
0
Baths
0 SqFt
Land
MLS® # OM650214
New
Active
$17,500,000
ISLEWORTH
9306 Blanche Cove Drive Dr, WINDERMERE
5
Beds
8
Baths
14,856 SqFt
Single Family Residence
MLS® # O6097686
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
$15,000,000
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
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
Active
$9,500,000
GOLDEN OAK PH 01C
10030 Enchanted Oak Dr, GOLDEN OAK
6
Beds
7
Baths
9,444 SqFt
Single Family Residence
MLS® # O6017000
Active
$9,500,000
17802 Old Ymca Rd, WINTER GARDEN
0
Beds
0
Baths
0 SqFt
Land
MLS® # O5968921
Active
$8,500,000
▼ $1,150,000
0000
1190 North Park Ave, WINTER PARK
8
Beds
10
Baths
19,619 SqFt
Single Family Residence
MLS® # O6039038
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
$8,250,000
▲ $1,255,000
METCALF PARK REP
11940 Lake Butler Blvd, WINDERMERE
5
Beds
7
Baths
6,549 SqFt
Single Family Residence
MLS® # O5992327
Active
$7,990,000
LAKE WHIPPOORWILL
10411 Tyson Rd, ORLANDO
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6081836
Active
$7,990,000
LAKE WHIPPOORWILL
10419 Tyson Rd, ORLANDO
3
Beds
2
Baths
3,300 SqFt
Single Family Residence
MLS® # O6080656
Active
$7,900,000
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
$7,900,000
▼ $1,050,000
J KRONENBERGER SUB
1311 Via Tuscany, WINTER PARK
7
Beds
8
Baths
10,997 SqFt
Single Family Residence
MLS® # O6011692
Active
$7,800,000
GOLDEN OAK PHASE 5
10217 Symphony Grove Dr, ORLANDO
5
Beds
7
Baths
5,241 SqFt
Single Family Residence
MLS® # O6048451
New
Active
$7,500,000
ISLEWORTH
5139 Isleworth Country Club Dr, WINDERMERE
7
Beds
8
Baths
13,973 SqFt
Single Family Residence
MLS® # O6097345
Active
$7,495,000
▲ $6,745,500
LAKE DOWN ESTATES
10988 Down Yonder Ln, WINDERMERE
4
Beds
6
Baths
8,446 SqFt
Single Family Residence
MLS® # O6021133
Active
$7,388,000
ISLEWORTH
9736 Chestnut Ridge Dr, WINDERMERE
5
Beds
7
Baths
7,625 SqFt
Single Family Residence
MLS® # O6080321
Active
$7,250,000
▼ $525,000
ISLEWORTH
9832 Laurel Valley Dr, WINDERMERE
6
Beds
10
Baths
11,100 SqFt
Single Family Residence
MLS® # O6043474
Active
$7,035,000
LAKE BUTLER ESTATES
11947 Lake Butler Blvd, WINDERMERE
6
Beds
9
Baths
14,364 SqFt
Single Family Residence
MLS® # O6065698
Active
$7,000,000
ISLEWORTH
9838 Laurel Valley Dr, WINDERMERE
5
Beds
9
Baths
10,843 SqFt
Single Family Residence
MLS® # O6060724
Active
$6,995,000
▼ $505,000
ACREAGE & UNREC
9520 Windy Ridge Rd, WINDERMERE
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6069467
Active
$6,750,000
▼ $1,209,000
SUNSET BAY REP
5020 Down Point Ln, WINDERMERE
8
Beds
8
Baths
9,621 SqFt
Single Family Residence
MLS® # O6030119
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
$6,500,000
▼ $1,400,000
MILLIONAIRE'S ROW
9726 Kilgore Rd, ORLANDO
5
Beds
9
Baths
12,370 SqFt
Single Family Residence
MLS® # O5570091
Active
$6,495,000
▼ $700,000
KEENES POINTE 46/104
6507 Rosella Ct, WINDERMERE
7
Beds
8
Baths
10,485 SqFt
Single Family Residence
MLS® # O6064654
Active
$6,395,000
METCALF PARK REP
11536 Lake Butler Blvd, WINDERMERE
6
Beds
8
Baths
8,204 SqFt
Single Family Residence
MLS® # O6094155
Active
$6,000,000
THE LAKE HOUSE
3801 Mckinnon Rd, WINDERMERE
6
Beds
15
Baths
24,080 SqFt
Single Family Residence
MLS® # O6090168
Active
$6,000,000
INTERNATIONAL COVE
6440 Canada Ave, ORLANDO
0
Beds
0
Baths
0 SqFt
Land
MLS® # O5347857
New
Active
$5,999,999
ISLEWORTH
9718 Green Island Cv, WINDERMERE
4
Beds
6
Baths
4,724 SqFt
Single Family Residence
MLS® # O6095851
Active
$5,995,000
▼ $455,000
RESERVE AT LAKE BUTLER SOUND 45/120
11049 Bridge House Rd, WINDERMERE
5
Beds
8
Baths
10,112 SqFt
Single Family Residence
MLS® # O6033684
Active
$5,850,000
▲ $1,729,000
N/A, APOPKA
0
Beds
0
Baths
6,562 SqFt
Land
MLS® # O5183153
Active
$5,805,000
1111 West Keene Rd, APOPKA
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6086552
Active
$5,495,000
▼ $300,000
BEVERLY SHORES
3260 Lake Shore Dr, ORLANDO
5
Beds
9
Baths
6,709 SqFt
Single Family Residence
MLS® # O6076310
Active
$5,000,000
WP KELLY 11
3243 West Kelly Park Rd, APOPKA
0
Beds
0
Baths
0 SqFt
Land
MLS® # G5056961
Active
$4,999,990
MOSS PARK RESERVE
10330 Wittenberg Way, ORLANDO
6
Beds
8
Baths
9,272 SqFt
Single Family Residence
MLS® # O6029473
Active
$4,999,000
THOMAS M HENKELS ADD
466 Henkel Cir, WINTER PARK
4
Beds
5
Baths
4,416 SqFt
Single Family Residence
MLS® # O6094004
Active
$4,950,000
▼ $550,000
ISLEWORTH
6474 Deacon Cir, WINDERMERE
6
Beds
6
Baths
5,859 SqFt
Single Family Residence
MLS® # O6042860
Active
$4,900,000
▼ $90,000
NO HOA
9575 Westover Roberts Rd, WINDERMERE
9
Beds
8
Baths
8,464 SqFt
Single Family Residence
MLS® # O6060334
Active
$4,900,000
▲ $400,000
LAKESIDE ESTATES
5640 Santa Rosa Dr, ORLANDO
0
Beds
0
Baths
0 SqFt
Land
MLS® # O5946302
Active
$4,900,000
OSCEOLA PLACE
550 Palmer Ave, WINTER PARK
5
Beds
8
Baths
5,952 SqFt
Single Family Residence
MLS® # O6029085
Active
$4,880,000
LIVINGSTON
1911 Silver Star Rd, ORLANDO
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6081664
Active
$4,699,995
ROSSER RESERVE REP
1005 Down Reserve Ct, WINDERMERE
6
Beds
8
Baths
9,754 SqFt
Single Family Residence
MLS® # O6053570
Active
$4,500,000
WINDERMERE REP
225 Magnolia St, WINDERMERE
7
Beds
11
Baths
5,735 SqFt
Single Family Residence
MLS® # O6079340
Active
$4,325,000
WINTER PARK TOWN OF
1106 Palmer Ave, WINTER PARK
4
Beds
6
Baths
6,256 SqFt
Single Family Residence
MLS® # O6043192
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:
- Audubon Villas At Hunters Creek
- Bay Hill
- Bay Lakes At Granada
- Berkshire Park
- Bermuda Dunes
- Blue Heron Beach Resort
- Brentwood Club
- Bristol Park
- Central Park Condo
- Charleston Place
- Courtney Landing
- Crest At Waterford Lakes
- Damai
- Discovery Palms
- Downtown Orlando
- Dr Phillips
- Eagle Creek
- Enclave At Orlando
- Floridays Resort Orlando
- Fountains at Metrowest
- Granada Villas
- Hamptons At Metrowest
- Hawthorn Suites
- Heritage Crossing At Reunion Resort
- Hidden Springs & Estates
- Hunters Creek
- Independence
- Isles At Cay Common
- Isleworth
- Keenes Point
- Kensington Park
- Lake Buena Vista Resort Village & Spa
- Lake Nona
- Lakeside At Lakes of Windermere
- Madison At Metrowest
- Metro At Michigan Park
- Miriada
- Mosaic At Millenia
- North Bay
- Orange Tree Country Club
- Palisades
- Palms Club
- Parc Corniche
- Plantation Park
- Point Orlando
- Residences At Villa Medici
- Riversbend
- Sanctuary At Bay Hill
- Sand Lake Hills
- Sand Lake Point
- Serenata
- South Bay
- Staysky Suites I-Drive Orlando
- Stonebridge Reserve
- Summerport
- Sunrise Lakes
- Sunset Lake Condo
- The Commons
- Torey Pines
- Toscana
- Tradewinds
- Ventura Reserve
- Visconti West
- Vista Cay
- Vistas At Stonebridge Commons
- Vizcaya
- Vue At Lake Eola
- Waverly On Lake Eola
- Westminster Gardens
- Westminster Landing
- Windermere
- Windermere Landings
- Woodbridge At Meadow Woods
- Worldquest
Are you interested in purchasing vacation property in Orange County? We encourage you to 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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