Orlando VACATION HOMES FOR SALE

City:  Celebration | ChampionsGate | Clermont | Davenport | Haines City | Kissimmee | Lake Buena Vista | Orlando | Reunion |  Windermere | Winter Garden

Most people only know Orlando, Florida as the Theme Park Capital of the World. But The City Beautiful, as it's also known as, offers much more including affordable living, a vibrant arts scene, plentiful shopping, spas, golf, dining, outdoor adventures and nightlife for residents and visitors to enjoy. The wonderful Orlando vacation homes for sale place residents at the center of it all!

For those wishing to buy a second home to use as a vacation home or for investment income, Orlando is an excellent choice. Sales taxes are low, and there are no state income taxes. Orlando is also home to the University of Central Florida, which is the largest university in the United States by undergraduate enrollment. 

Check out the available Orlando vacation real estate listings below, or continue reading to learn more about the many wonderful holiday communities found in the city!

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FEATURED
Active 5025 Shoreway Loop 307, ORLANDO

$609,950

▼ $20,000 VISTA CAY

5025 Shoreway Loop 307, ORLANDO

3 Beds 2 Baths 2,097 SqFt Condominium MLS® # S5098137
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 8125 Resort Village Dr 5906, ORLANDO

$214,950

LAKE BUENA VISTA RESORT

8125 Resort Village Dr 5906, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5095011
FEATURED
Active 8000 Poinciana Blvd 2606, ORLANDO

$181,000

▼ $7,000 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

$124,000

▼ $5,950 STAYSKY SUITES, HAWTHORN SUITES

7601 Canada Ave 305, ORLANDO

1 Bed 1 Bath 542 SqFt Condo - Hotel MLS® # S5098440
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 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
New
Active 7625 Clarcona Ocoee Rd, ORLANDO

$6,999,999

NONE

7625 Clarcona Ocoee Rd, ORLANDO

2 Beds 2 Baths 6,610 SqFt Single Family Residence MLS® # O6174081
Active 9220 Point Cypress Dr, ORLANDO

$6,990,000

▼ $10,000 CYPRESS POINT PH 02

9220 Point Cypress Dr, ORLANDO

6 Beds 9 Baths 8,247 SqFt Single Family Residence MLS® # O6148371
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 5619 Emerson Pointe Way, ORLANDO

$5,150,000

EMERSON POINTE

5619 Emerson Pointe Way, ORLANDO

4 Beds 7 Baths 7,602 SqFt Single Family Residence MLS® # O6180244
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
Active 11998 Moss Park Rd, ORLANDO

$4,000,000

11998 Moss Park Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6109805
Active 10330 Wittenberg Way, ORLANDO

$3,999,000

▼ $251,000 MOSS PARK RESERVE

10330 Wittenberg Way, ORLANDO

6 Beds 8 Baths 9,272 SqFt Single Family Residence MLS® # O6029473
Active 8545 Lake Nona Shore Dr, ORLANDO

$3,890,000

▼ $85,000 LAKE NONA ESTATES

8545 Lake Nona Shore Dr, ORLANDO

5 Beds 7 Baths 6,484 SqFt Single Family Residence MLS® # O6120079
Active 4429 North Orange Blossom Tr, ORLANDO

$3,850,000

WOFFORD PROP

4429 North Orange Blossom Tr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6180711
Active 2701 Ardsley Dr, ORLANDO

$3,600,000

ARDSLEY MANOR SUB

2701 Ardsley Dr, ORLANDO

5 Beds 6 Baths 5,095 SqFt Single Family Residence MLS® # O6182425
Active 6413 Beth Rd, ORLANDO

$3,600,000

ORLANDO KISSIMMEE FARMS

6413 Beth Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # S5094874
Active International Dr, ORLANDO

$3,532,500

WILLIS R MUNGERS LAND SUB

International Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6147758
Active 1400 Nottingham St, ORLANDO

$3,500,000

▲ $501,000 BEVERLY SHORES

1400 Nottingham St, ORLANDO

5 Beds 5 Baths 4,266 SqFt Single Family Residence MLS® # O6086414
Active 10245 Trout Rd, ORLANDO

$3,500,000

▼ $450,000 CYPRESS SHORES

10245 Trout Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6111931
Active 10245 Trout Rd, ORLANDO

$3,500,000

▼ $450,000 CYPRESS SHORES

10245 Trout Rd, ORLANDO

3 Beds 2 Baths 1,440 SqFt Single Family Residence MLS® # O6111899
Active 2201 South Goldenrod Rd, ORLANDO

$3,499,000

▲ $799,000 ORLANDO TERRACE SEC 01

2201 South Goldenrod Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6039497
Active 1411 Nottingham St, ORLANDO

$3,300,000

BEVERLY SHORES

1411 Nottingham St, ORLANDO

5 Beds 5 Baths 3,948 SqFt Single Family Residence MLS® # O6178116
Active 5919 Masters Blvd, ORLANDO

$3,300,000

BAY HILL SEC 13

5919 Masters Blvd, ORLANDO

4 Beds 4 Baths 4,175 SqFt Single Family Residence MLS® # O6166803
Active 4171 North Orange Blossom Tr, ORLANDO

$3,300,000

▲ $300,000 FAIRVIEW POINTE

4171 North Orange Blossom Tr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6101065
Active International, ORLANDO

$3,290,000

International, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6147797
Active 1648 Harston Ave, ORLANDO

$3,256,000

BALDWIN PARK UN #9A

1648 Harston Ave, ORLANDO

4 Beds 5 Baths 5,128 SqFt Single Family Residence MLS® # O6178784
Active 5070 Benwick Alley, ORLANDO

$3,250,000

BALDWIN PARK REP 1

5070 Benwick Alley, ORLANDO

5 Beds 7 Baths 4,568 SqFt Single Family Residence MLS® # O6176007
Active 6000 South Semoran Blvd, ORLANDO

$3,250,000

6000 South Semoran Blvd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # T3502458
Active 2615 South Goldenrod Rd, ORLANDO

$3,250,000

GOLDEN ACRES SEC B

2615 South Goldenrod Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # S5091180
Active 2293 Sand Lake Rd, ORLANDO

$3,200,000

ORLANDO CENTRAL PARK 34

2293 Sand Lake Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6158228
Active 8622 Farthington Way, ORLANDO

$3,100,000

LAKE NONA ESTATES

8622 Farthington Way, ORLANDO

4 Beds 5 Baths 2,934 SqFt Single Family Residence MLS® # O6182400
Active 8020 Firenze Blvd, ORLANDO

$2,999,999

VIZCAYA PH 01 45/29

8020 Firenze Blvd, ORLANDO

5 Beds 7 Baths 5,898 SqFt Single Family Residence MLS® # O6163413
Active 9718 Kilgore Rd, ORLANDO

$2,999,000

▼ $200,000 ACREAGE

9718 Kilgore Rd, ORLANDO

5 Beds 4 Baths 4,321 SqFt Single Family Residence MLS® # O6141295
Active 8962 Royal Birkdale Ln, ORLANDO

$2,985,000

BAY HILL

8962 Royal Birkdale Ln, ORLANDO

6 Beds 7 Baths 5,305 SqFt Single Family Residence MLS® # O6175809
New
Active 6747 Whispering Pines Rd, ORLANDO

$2,975,000

ORLANDO-KISSIMMEE FARMS

6747 Whispering Pines Rd, ORLANDO

6 Beds 3 Baths 3,858 SqFt Single Family Residence MLS® # S5100906
Active 10109 Tavistock Rd, ORLANDO

$2,950,000

▼ $345,000 LAKE NONA ESTATES

10109 Tavistock Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6097146
Active 5762 Emerington Cres, ORLANDO

$2,950,000

EMERSON POINTE

5762 Emerington Cres, ORLANDO

5 Beds 6 Baths 5,138 SqFt Single Family Residence MLS® # O6179491
Active 222 North Parramore Ave, ORLANDO

$2,900,000

▼ $600,000 SUNSET PARK SUB

222 North Parramore Ave, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6045853
Active 8125 Via Rosa, ORLANDO

$2,869,000

▼ $100,000 MIRABELLA/VIZCAYA PH 03

8125 Via Rosa, ORLANDO

4 Beds 5 Baths 4,592 SqFt Single Family Residence MLS® # O6140907
Active 1204 41st St, ORLANDO

$2,800,000

ARMSTRONG ACRES

1204 41st St, ORLANDO

5 Beds 4 Baths 4,021 SqFt Single Family Residence MLS® # S5085001
Active Kilgore Rd, ORLANDO

$2,800,000

Kilgore Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6083514

The Orlando Community

Orlando’s history dates back to the 1800s, when the U.S. Army established an outpost south of the current downtown during the Second Seminole War. The town later became the county seat of the new Orange County in 1856, and enjoyed status as the hub of the state’s citrus industry in the late 1800s.

Tourism became the driving force in Orlando’s economy after Walt Disney World opened in 1971. Since then, Universal Orlando, Sea World, Gatorland and other attractions have successfully attracted millions of visitors from around the globe. Health care is also a growing economic driver, with the addition of the University of Central Florida medical school and the hospitals, research facilities and other establishments located in the new Lake Nona Medical City area. 

Orlando Real Estate Market 

The historic core of “Old Orlando” lies along Church Street, between Orange and Garland Avenues downtown. This historic district includes the Lake Eola Heights and Thornton Park neighborhoods, which feature some of the oldest homes in the city. 

There are also plenty of newer housing communities in Orlando, offering a range of options such as single family homes, townhomes, condos and condo/hotels. Short-term rentals are only allowed in condos and townhomes, with most being offered in resort-style communities located near Disney World, such as Floridays Orlando, Lake Buena Vista and Blue Heron Beach.

Browse Orlando Holiday Home Communities:

Communities in Orlando, Florida:


If you’d like more information about purchasing an Olando vacation home, contact a Team Donovan agent at 407-704-2616 or or visit us online.

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