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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

Orlando ResortsBlue Heron Beach Resort - Floridays Resort OrlandoGolden Oak at Walt Disney World - Hawthorn Suites Orlando Lake Buena VistaIsles At Cay CommonLake Berkley - Lake Buena Vista Resort Village & SpaParadiso Grande - Parc Corniche - Point OrlandoStaySky Suites I-Drive OrlandoThe Enclave Suites OrlandoVista CayWorldquest Resort

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!

Search Orlando Real Estate Listings

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FEATURED
Active 150 East Robinson St 219, ORLANDO

$334,950

THE VUE AT LAKE EOLA

150 East Robinson St 219, ORLANDO

1 Bed 2 Baths 925 SqFt Condominium MLS® # S5122537
FEATURED
Active 12539 Floridays Resort Drive 305-d, ORLANDO

$244,900

FLORIDAYS RESORT

12539 Floridays Resort Drive 305-d, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5105392
FEATURED
Active 8112 Poinciana Blvd 1706, ORLANDO

$225,000

LAKE BUENA VISTA RESORT

8112 Poinciana Blvd 1706, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5112618
FEATURED
Active 12527 Floridays Resort Dr E-103, ORLANDO

$209,950

▼ $5,000 FLORIDAYS RESORT

12527 Floridays Resort Dr E-103, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5114808
New FEATURED
Active 911 North Orange Ave 550, ORLANDO

$199,950

UPTOWN PLACE

911 North Orange Ave 550, ORLANDO

2 Beds 2 Baths 1,075 SqFt Condominium MLS® # S5122935
FEATURED
Active 8101 Resort Village Drive B3/u3601, ORLANDO

$199,950

LAKE BUENA VISTA RESORT

8101 Resort Village Drive B3/u3601, ORLANDO

3 Beds 2 Baths 1,231 SqFt Condo - Hotel MLS® # S5119669
FEATURED
Active 8100 Poinciana Blvd 2501, ORLANDO

$198,950

LAKE BUENA VISTA RESORT

8100 Poinciana Blvd 2501, ORLANDO

3 Beds 2 Baths 1,231 SqFt Condo - Hotel MLS® # S5120932
FEATURED
Active 8101 Resort Village Dr 3712, ORLANDO

$179,900

▼ $20,000 LAKE BUENA VISTA RESORT

8101 Resort Village Dr 3712, ORLANDO

3 Beds 2 Baths 1,231 SqFt Condo - Hotel MLS® # S5121941
FEATURED
Active 8100 Poinciana Boulevard B2/u2511, ORLANDO

$179,500

LAKE BUENA VISTA RESORT

8100 Poinciana Boulevard B2/u2511, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5119899
FEATURED
Active 8100 Poinciana Blvd 2703, ORLANDO

$172,000

LAKE BUENA VISTA RESORT

8100 Poinciana Blvd 2703, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5119192
FEATURED
Active 8125 Resort Village Dr 5705, ORLANDO

$164,950

▼ $35,000 LAKE BUENA VISTA RESORT

8125 Resort Village Dr 5705, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5106607
Active 6447 Grand National Dr, ORLANDO

$21,750,000

▲ $2,000,000 SHOPPERS WORLD

6447 Grand National Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6249921
Active 9291 Point Cypress Dr, ORLANDO

$19,500,000

CYPRESS POINT PH 02

9291 Point Cypress Dr, ORLANDO

12 Beds 14 Baths 14,706 SqFt Single Family Residence MLS® # O6280213
Active 1955 South Apopka Vineland Rd, ORLANDO

$11,800,000

1955 South Apopka Vineland Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6211968
Active Moss Park Rd, ORLANDO

$8,900,000

Moss Park Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5903841
Active 9122 Bay Point Dr, ORLANDO

$7,995,000

BAY POINT

9122 Bay Point Dr, ORLANDO

4 Beds 6 Baths 5,654 SqFt Single Family Residence MLS® # O6273889
Active 9726 Kilgore Rd, ORLANDO

$7,900,000

▼ $2,000,000 N/A

9726 Kilgore Rd, ORLANDO

4 Beds 6 Baths 10,010 SqFt Single Family Residence MLS® # O6229408
Active 10424 Pocket Ln, ORLANDO

$7,639,995

▼ $250,000 WILLIS R MUNGERS LAND SUB

10424 Pocket Ln, ORLANDO

5 Beds 7 Baths 7,500 SqFt Single Family Residence MLS® # O6219322
Active 2725 Rayburn St, ORLANDO

$7,600,000

PROSPER COLONY 06-24-30

2725 Rayburn St, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6275444
Active 9164 Point Cypress Dr, ORLANDO

$6,750,000

CYPRESS POINT

9164 Point Cypress Dr, ORLANDO

5 Beds 8 Baths 7,631 SqFt Single Family Residence MLS® # O6243016
Active 9138 Bay Point Dr, ORLANDO

$6,350,000

BAY POINT

9138 Bay Point Dr, ORLANDO

4 Beds 5 Baths 6,018 SqFt Single Family Residence MLS® # O6284085
Active 9105 Sheen Sound St, ORLANDO

$5,995,000

▲ $500,000 LAKE SHEEN SOUND

9105 Sheen Sound St, ORLANDO

5 Beds 8 Baths 7,147 SqFt Single Family Residence MLS® # O6261887
Active 9202 Bay Point Dr, ORLANDO

$5,900,000

▼ $50,000 BAY POINT

9202 Bay Point Dr, ORLANDO

5 Beds 7 Baths 8,844 SqFt Single Family Residence MLS® # T3542430
Active 11043 Cromwell Rd, ORLANDO

$5,495,000

LAKE NONA CENTRAL

11043 Cromwell Rd, ORLANDO

5 Beds 7 Baths 6,056 SqFt Single Family Residence MLS® # O6276285
Active 11027 Cromwell Rd, ORLANDO

$5,299,000

▲ $324,000 LAKE NONA ESTATES 10

11027 Cromwell Rd, ORLANDO

5 Beds 8 Baths 7,070 SqFt Single Family Residence MLS® # O6201991
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 7017 Via Carmel Way, ORLANDO

$4,950,000

CARMEL

7017 Via Carmel Way, ORLANDO

5 Beds 6 Baths 6,202 SqFt Single Family Residence MLS® # O6276258
Active 5745 Emerington Cres, ORLANDO

$4,940,000

▼ $50,000 EMERSON POINTE

5745 Emerington Cres, ORLANDO

7 Beds 8 Baths 7,881 SqFt Single Family Residence MLS® # O6184236
Active 5640 Santa Rosa Dr, ORLANDO

$4,900,000

▲ $400,000 LAKESIDE ESTATES

5640 Santa Rosa Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5946302
Active 8643 Farthington Way, ORLANDO

$4,660,950

▲ $365,950 LAKE NONA ESTATES

8643 Farthington Way, ORLANDO

5 Beds 7 Baths 5,487 SqFt Single Family Residence MLS® # O6232183
Active 8968 Bay Cove Ct, ORLANDO

$4,549,999

▼ $1 BAY HILL SEC 04

8968 Bay Cove Ct, ORLANDO

6 Beds 7 Baths 5,428 SqFt Single Family Residence MLS® # O6272983
Active 8966 Easterling Dr, ORLANDO

$4,299,995

▼ $4 BAY HILL SEC 05

8966 Easterling Dr, ORLANDO

4 Beds 5 Baths 3,987 SqFt Single Family Residence MLS® # O6279143
Active 350 South 5th St, ORLANDO

$4,000,000

NONE

350 South 5th St, ORLANDO

3 Beds 2 Baths 1,728 SqFt Single Family Residence MLS® # O6252720
Active 10716 & 10700 Golden Cypress Ct, ORLANDO

$3,999,000

▼ $296,000 WILLIS R MUNGERS LAND SUB

10716 & 10700 Golden Cypress Ct, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6211532
Active 9213 Foxhall Ct, ORLANDO

$3,995,000

NORTH BAY SEC IV-A

9213 Foxhall Ct, ORLANDO

5 Beds 7 Baths 6,700 SqFt Single Family Residence MLS® # O6274006
Active 6009 Lady Bet Dr, ORLANDO

$3,899,980

▼ $98,600 POINTE TIBET REP

6009 Lady Bet Dr, ORLANDO

4 Beds 5 Baths 4,695 SqFt Single Family Residence MLS® # O6261183
Active 10244 Kensington Shore Dr, ORLANDO

$3,800,000

LAKE NONA ESTATES

10244 Kensington Shore Dr, ORLANDO

5 Beds 5 Baths 4,574 SqFt Single Family Residence MLS® # O6261841
Active 9589 Blandford Rd, ORLANDO

$3,800,000

▼ $700,000 LAKE NONA ESTATES

9589 Blandford Rd, ORLANDO

5 Beds 7 Baths 6,101 SqFt Single Family Residence MLS® # O6195396
Active 6025 Lady Bet Dr, ORLANDO

$3,750,000

▼ $49,000 POINTE TIBET REP

6025 Lady Bet Dr, ORLANDO

4 Beds 5 Baths 4,500 SqFt Single Family Residence MLS® # O6268221
Active 9847 Laurel Berry Dr, ORLANDO

$3,700,000

LAUREL POINTE

9847 Laurel Berry Dr, ORLANDO

6 Beds 7 Baths 7,093 SqFt Single Family Residence MLS® # O6272573
Active 11421 Tindall Rd, ORLANDO

$3,690,000

▼ $60,000 ACREAGE & UNREC

11421 Tindall Rd, ORLANDO

6 Beds 7 Baths 6,213 SqFt Single Family Residence MLS® # O6247168
Active 9212 Island Lake Ct, ORLANDO

$3,650,000

WATERS EDGE BOCA POINTE AT TURTLE CREEK

9212 Island Lake Ct, ORLANDO

4 Beds 5 Baths 5,776 SqFt Single Family Residence MLS® # O6284668
Active 4654 Thornlea Rd, ORLANDO

$3,649,000

WAUNATTA SHORES

4654 Thornlea Rd, ORLANDO

5 Beds 6 Baths 5,290 SqFt Single Family Residence MLS® # O6286235
New
Active 9372 Thurloe Pl, ORLANDO

$3,500,000

LAKE NONA PH 01A PRCL 03

9372 Thurloe Pl, ORLANDO

4 Beds 5 Baths 5,150 SqFt Single Family Residence MLS® # O6291795
Active 8441 Oakland Pl, ORLANDO

$3,500,000

WINDERMERE HEIGHTS ADD 02

8441 Oakland Pl, ORLANDO

5 Beds 5 Baths 4,828 SqFt Single Family Residence MLS® # O6204737
Active 5950 Masters Blvd, ORLANDO

$3,499,999

BAY HILL SEC 13

5950 Masters Blvd, ORLANDO

6 Beds 7 Baths 10,402 SqFt Single Family Residence MLS® # O6286652
Active 9138 Great Heron Cir, ORLANDO

$3,497,777

CYPRESS POINT

9138 Great Heron Cir, ORLANDO

5 Beds 5 Baths 6,443 SqFt Single Family Residence MLS® # O6270507
Active 1948 Rowena Ave, ORLANDO

$3,450,000

MERRITT PARK

1948 Rowena Ave, ORLANDO

5 Beds 8 Baths 4,790 SqFt Single Family Residence MLS® # O6258640

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 407-705-2616 or or visit us online.

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