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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 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 8112 Poinciana Blvd 1509, ORLANDO

$199,950

LAKE BUENA VISTA RESORT

8112 Poinciana Blvd 1509, ORLANDO

3 Beds 3 Baths 1,409 SqFt Condo - Hotel MLS® # S5101673
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 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
Active 14154 Ward Rd, ORLANDO

$6,500,000

LAKE PRESERVE

14154 Ward Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # S5102984
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 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 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 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 5619 Emerson Pointe Way, ORLANDO

$4,850,000

▼ $300,000 EMERSON POINTE

5619 Emerson Pointe Way, ORLANDO

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

$4,000,000

11998 Moss Park Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6109805
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 3412 Oranole Rd, ORLANDO

$3,750,000

3412 Oranole Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # V4931722
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 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 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 6000 South Semoran Blvd, ORLANDO

$3,250,000

6000 South Semoran Blvd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # T3502458
New
Active 8150 Curry Ford Rd, ORLANDO

$3,200,000

8150 Curry Ford Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # S5102977
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 5919 Masters Blvd, ORLANDO

$3,190,000

▼ $110,000 BAY HILL SEC 13

5919 Masters Blvd, ORLANDO

4 Beds 4 Baths 4,175 SqFt Single Family Residence MLS® # O6166803
Active 10525 Cromwell Grove Ter, ORLANDO

$3,150,000

LAKE NONA PH 01A PRCL 03

10525 Cromwell Grove Ter, ORLANDO

5 Beds 6 Baths 4,450 SqFt Single Family Residence MLS® # O6192739
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 5070 Benwick Alley, ORLANDO

$3,100,000

▼ $150,000 BALDWIN PARK REP 1

5070 Benwick Alley, ORLANDO

5 Beds 7 Baths 4,568 SqFt Single Family Residence MLS® # O6176007
Active 1427 North Semoran Blvd, ORLANDO

$3,100,000

▲ $105,000 LEAWOOD

1427 North Semoran Blvd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6089209
Active 3604 West New Hampshire St, ORLANDO

$3,000,000

WILLIS R MUNGERS LAND SUB

3604 West New Hampshire St, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6194366
Active 1411 Nottingham St, ORLANDO

$2,999,999

▼ $300,001 BEVERLY SHORES

1411 Nottingham St, ORLANDO

5 Beds 5 Baths 3,948 SqFt Single Family Residence MLS® # O6178116
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 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
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 6747 Whispering Pines Rd, ORLANDO

$2,950,000

▼ $25,000 ORLANDO-KISSIMMEE FARMS

6747 Whispering Pines Rd, ORLANDO

6 Beds 3 Baths 3,858 SqFt Single Family Residence MLS® # S5100906
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

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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