SEARCH > ALL COMMUNITIES > COUNTY > CITY > ZIP > SINGLE FAMILY HOME > TOWNHOUSE > CONDOMINIUM > CONDO - HOTEL > SHORT TERM RENTAL > RESORTS

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

Click the links below to sort results by price range.

Sort by:
FEATURED
Active 12544 Floridays Resort Drive 506-b, ORLANDO

$265,000

FLORIDAYS RESORT

12544 Floridays Resort Drive 506-b, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5105523
FEATURED
Active 12556 Floridays Resort Drive 304-a, ORLANDO

$263,950

▼ $5,050 FLORIDAYS RESORT

12556 Floridays Resort Drive 304-a, ORLANDO

3 Beds 2 Baths 1,200 SqFt Condo - Hotel MLS® # S5105047
FEATURED
Active 12521 Floridays Resort Drive 404-f, ORLANDO

$258,950

FLORIDAYS RESORT

12521 Floridays Resort Drive 404-f, ORLANDO

3 Beds 2 Baths 1,200 SqFt Condo - Hotel MLS® # S5107545
FEATURED
Active 13415 Blue Heron Beach Dr 103, ORLANDO

$249,900

▼ $10,000 BLUE HERON BEACH RESORT

13415 Blue Heron Beach Dr 103, ORLANDO

1 Bed 2 Baths 798 SqFt Condo - Hotel MLS® # S5106710
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 8125 Resort Village Dr 5705, ORLANDO

$199,950

LAKE BUENA VISTA RESORT

8125 Resort Village Dr 5705, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5106607
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

▼ $1,500,000 GOLDEN OAK PHASE 3

10242 Summer Meadow Way, ORLANDO

7 Beds 10 Baths 9,254 SqFt Single Family Residence MLS® # O6101583
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 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 Moss Park Rd, ORLANDO

$8,900,000

Moss Park Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5903841
Active 7766 Wandering Way, ORLANDO

$8,100,000

▼ $1,200,000 PHILLIPS GROVE

7766 Wandering Way, ORLANDO

7 Beds 8 Baths 6,736 SqFt Single Family Residence MLS® # O6161203
Active 10424 Pocket Ln, ORLANDO

$7,895,000

WILLIS R MUNGERS LAND SUB

10424 Pocket Ln, ORLANDO

5 Beds 7 Baths 5,800 SqFt Single Family Residence MLS® # O6219322
New
Active 9202 Bay Point Dr, ORLANDO

$7,000,000

BAY POINT

9202 Bay Point Dr, ORLANDO

5 Beds 7 Baths 8,844 SqFt Single Family Residence MLS® # T3542430
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

$5,999,500

▼ $195,500 ISLE OF OSPREY

5550 Osprey Isle Ln, ORLANDO

5 Beds 6 Baths 6,730 SqFt Single Family Residence MLS® # O6115072
Active 10716 & 10700 Golden Cypress Ct, ORLANDO

$5,900,000

WILLIS R MUNGERS LAND SUB

10716 & 10700 Golden Cypress Ct, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6211532
Active 5745 Emerington Cres, ORLANDO

$5,090,000

▼ $50,000 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 11027 Cromwell Rd, ORLANDO

$4,975,000

LAKE NONA ESTATES 10

11027 Cromwell Rd, ORLANDO

5 Beds 8 Baths 6,355 SqFt Single Family Residence MLS® # O6201991
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 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 9589 Blandford Rd, ORLANDO

$4,500,000

LAKE NONA PH 01A PRCL 11

9589 Blandford Rd, ORLANDO

5 Beds 7 Baths 6,101 SqFt Single Family Residence MLS® # O6195396
Active 11059 Cromwell Rd, ORLANDO

$4,395,000

LAKE NONA ESTATES 10

11059 Cromwell Rd, ORLANDO

5 Beds 7 Baths 5,866 SqFt Single Family Residence MLS® # O6201958
Active 10409 Trout Rd, ORLANDO

$4,200,000

CYPRESS SHORES

10409 Trout Rd, ORLANDO

6 Beds 5 Baths 5,625 SqFt Single Family Residence MLS® # O6208545
Active 9501 Tavistock Rd, ORLANDO

$3,950,000

LAKE NONA GOLF & COUNTRY CLUB

9501 Tavistock Rd, ORLANDO

5 Beds 5 Baths 4,878 SqFt Single Family Residence MLS® # O6195103
Active 3207 Middlesex Rd, ORLANDO

$3,895,000

BEVERLY SHORES

3207 Middlesex Rd, ORLANDO

5 Beds 7 Baths 4,944 SqFt Single Family Residence MLS® # O6199693
Active 11019 Cromwell Rd, ORLANDO

$3,875,000

LAKE NONA ESTATES 10

11019 Cromwell Rd, ORLANDO

5 Beds 7 Baths 4,625 SqFt Single Family Residence MLS® # O6202148
Active 9138 Great Heron Cir, ORLANDO

$3,750,000

CYPRESS POINT

9138 Great Heron Cir, ORLANDO

5 Beds 5 Baths 6,443 SqFt Single Family Residence MLS® # O6211617
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 10262 Chiltern Garden Dr, ORLANDO

$3,500,000

LAKE NONA ESTATES

10262 Chiltern Garden Dr, ORLANDO

5 Beds 6 Baths 4,180 SqFt Single Family Residence MLS® # O6207873
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 1400 Nottingham St, ORLANDO

$3,500,000

▲ $501,000 BEVERLY SHORES

1400 Nottingham St, ORLANDO

5 Beds 6 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 6000 Tarawood Dr, ORLANDO

$3,499,000

BAY HILL SEC 09

6000 Tarawood Dr, ORLANDO

5 Beds 7 Baths 6,252 SqFt Single Family Residence MLS® # O6184254
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 4429 North Orange Blossom Tr, ORLANDO

$3,450,000

▼ $400,000 WOFFORD PROP

4429 North Orange Blossom Tr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6180711
Active 8959 Bay Cove Ct, ORLANDO

$3,350,000

▼ $240,000 BAY HILL SEC 04

8959 Bay Cove Ct, ORLANDO

3 Beds 4 Baths 5,201 SqFt Single Family Residence MLS® # O6209742
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 10227 Trout Rd, ORLANDO

$3,250,000

CYPRESS SHORES

10227 Trout Rd, ORLANDO

4 Beds 3 Baths 3,195 SqFt Single Family Residence MLS® # O6210457
Active 1693 Foss Ave, ORLANDO

$3,250,000

▼ $250,000 BALDWIN PARK

1693 Foss Ave, ORLANDO

5 Beds 7 Baths 5,288 SqFt Single Family Residence MLS® # O6200120

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.

^ Back to: City Search