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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 4862 Cayview Ave 407, ORLANDO

$425,000

▼ $9,999 VISTA CAY

4862 Cayview Ave 407, ORLANDO

2 Beds 2 Baths 1,112 SqFt Condominium MLS® # S5124892
FEATURED
Active 8774 Worldquest Blvd 7307, ORLANDO

$324,999

WORLDQUEST RESORT

8774 Worldquest Blvd 7307, ORLANDO

3 Beds 2 Baths 1,421 SqFt Condo - Hotel MLS® # S5137664
FEATURED
Active 8774 Worldquest Blvd 7404, ORLANDO

$294,999

WORLDQUEST RESORT

8774 Worldquest Blvd 7404, ORLANDO

3 Beds 3 Baths 1,459 SqFt Condo - Hotel MLS® # S5130693
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 12539 Floridays Resort Drive 305-d, ORLANDO

$215,000

FLORIDAYS RESORT

12539 Floridays Resort Drive 305-d, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5105392
FEATURED
Active 8100 Poinciana Blvd 2501, ORLANDO

$176,500

▼ $8,000 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 3506, ORLANDO

$159,999

▼ $10,000 LAKE BUENA VISTA RESORT

8101 Resort Village Dr 3506, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5136606
FEATURED
Active 8100 Poinciana Boulevard B2/u2511, ORLANDO

$159,500

▼ $20,000 LAKE BUENA VISTA RESORT

8100 Poinciana Boulevard B2/u2511, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5119899
FEATURED
Active 6172 Peregrine Ave, ORLANDO

$149,900

▼ $10,000 WINDHOVER

6172 Peregrine Ave, ORLANDO

1 Bed 1 Bath 591 SqFt Condominium MLS® # S5134563
FEATURED
Active 1051 S Hiawassee Rd 2127, ORLANDO

$143,900

▼ $15,000 TRADEWINDS

1051 S Hiawassee Rd 2127, ORLANDO

2 Beds 2 Baths 934 SqFt Condominium MLS® # S5124459
FEATURED
Active 8112 Poinciana Blvd 1303, ORLANDO

$139,999

▼ $10,000 LAKE BUENA VISTA RESORT

8112 Poinciana Blvd 1303, ORLANDO

2 Beds 2 Baths 1,060 SqFt Condo - Hotel MLS® # S5136600
FEATURED
Active 1091 S Hiawassee Rd 216, ORLANDO

$125,000

TRADEWINDS

1091 S Hiawassee Rd 216, ORLANDO

1 Bed 1 Bath 627 SqFt Condominium MLS® # S5120181
Active 11990 International Dr, ORLANDO

$16,000,000

ORANGEWOOD NEIGHBORHOOD-2

11990 International Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # A4668777
Active 7011 Via Carmel Way, ORLANDO

$12,000,000

▲ $1,500,000 CARMEL

7011 Via Carmel Way, ORLANDO

5 Beds 10 Baths 10,519 SqFt Single Family Residence MLS® # O6320806
Active 1955 S Apopka Vineland Rd, ORLANDO

$11,800,000

1955 S 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 9726 Kilgore Rd, ORLANDO

$7,900,000

N/A

9726 Kilgore Rd, ORLANDO

4 Beds 6 Baths 10,010 SqFt Single Family Residence MLS® # O6339007
Active 8774 Lake Tibet Ct, ORLANDO

$7,500,000

CYPRESS POINT

8774 Lake Tibet Ct, ORLANDO

5 Beds 8 Baths 7,043 SqFt Single Family Residence MLS® # O6353160
Active 9564 Kilgore Rd, ORLANDO

$7,500,000

NA

9564 Kilgore Rd, ORLANDO

6 Beds 8 Baths 7,313 SqFt Single Family Residence MLS® # O6338462
Active 4289 Chuluota Rd, ORLANDO

$6,795,000

0000

4289 Chuluota Rd, ORLANDO

5 Beds 10 Baths 7,521 SqFt Single Family Residence MLS® # O6349568
Active 9700 Blandford Rd, ORLANDO

$6,750,000

▲ $792,000 LAKE NONA ESTATES

9700 Blandford Rd, ORLANDO

5 Beds 7 Baths 6,732 SqFt Single Family Residence MLS® # O6332582
New
Active 1920 Lakeside Dr, ORLANDO

$6,295,000

MERRITT PARK

1920 Lakeside Dr, ORLANDO

5 Beds 6 Baths 5,964 SqFt Single Family Residence MLS® # O6358634
Active 10224 Mattraw Pl, ORLANDO

$6,250,000

▼ $245,000 GOLDEN OAK PH 2B & 2C

10224 Mattraw Pl, ORLANDO

5 Beds 5 Baths 3,753 SqFt Single Family Residence MLS® # O6332301
Active 9671 Blandford Rd, ORLANDO

$6,100,000

▲ $42,000 LAKE NONA ESTATES

9671 Blandford Rd, ORLANDO

5 Beds 7 Baths 6,058 SqFt Single Family Residence MLS® # O6332537
Active 10481 Cromwell Grove Ter, ORLANDO

$6,019,000

▲ $269,000 LAKE NONA PH 01A PRCL 03

10481 Cromwell Grove Ter, ORLANDO

6 Beds 7 Baths 6,019 SqFt Single Family Residence MLS® # O6342974
Active 5550 Osprey Isle Ln, ORLANDO

$5,695,000

ISLE OF OSPREY

5550 Osprey Isle Ln, ORLANDO

5 Beds 6 Baths 6,730 SqFt Single Family Residence MLS® # O6303377
Active 10160 Autumn Mist Ln 302, ORLANDO

$5,600,000

▲ $133,625 GOLDEN OAK FLORIAN PARK CONDOMINIUM

10160 Autumn Mist Ln 302, ORLANDO

3 Beds 4 Baths 3,715 SqFt Condominium MLS® # O6276114
Active 11043 Cromwell Rd, ORLANDO

$5,495,000

LAKE NONA ESTATES 10

11043 Cromwell Rd, ORLANDO

5 Beds 7 Baths 6,056 SqFt Single Family Residence MLS® # O6276285
Active 9602 Sloane St, ORLANDO

$5,285,000

LAKE NONA ESTATES

9602 Sloane St, ORLANDO

5 Beds 6 Baths 6,206 SqFt Single Family Residence MLS® # O6334371
Active 6440 Canada Ave, ORLANDO

$5,000,000

INTERNATIONAL COVE

6440 Canada Ave, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5347857
Active 9245 Southern Breeze Dr, ORLANDO

$4,700,000

ESTATES AT PHILLIPS LANDING PH 02

9245 Southern Breeze Dr, ORLANDO

6 Beds 8 Baths 6,790 SqFt Single Family Residence MLS® # O6344799
Active 8643 Farthington Way, ORLANDO

$4,660,950

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

$4,550,000

BAY HILL SEC 04

8968 Bay Cove Ct, ORLANDO

6 Beds 7 Baths 5,428 SqFt Single Family Residence MLS® # O6351771
Active 12335 Winter Garden Rd, ORLANDO

$4,500,000

12335 Winter Garden Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6320335
Active 8600 Hata St, ORLANDO

$4,499,999

PRESERVE/LAUREATE PARK PH 3

8600 Hata St, ORLANDO

5 Beds 6 Baths 5,718 SqFt Single Family Residence MLS® # O6335502
Active 9916 Lone Tree Ln, ORLANDO

$4,200,000

CYPRESS SHORES FIRST ADD

9916 Lone Tree Ln, ORLANDO

5 Beds 6 Baths 4,600 SqFt Single Family Residence MLS® # O6349925
Active 4733 Chuluota Rd, ORLANDO

$4,000,000

NONE

4733 Chuluota Rd, ORLANDO

4 Beds 4 Baths 4,094 SqFt Single Family Residence MLS® # O6348789
Active 100 S Eola Dr 119, ORLANDO

$4,000,000

SANCTUARY DOWNTOWN CONDO

100 S Eola Dr 119, ORLANDO

3 Beds 4 Baths 4,244 SqFt Condominium MLS® # O6295899
Active 9233 Southern Breeze Dr, ORLANDO

$3,985,000

▼ $5,000 ESTATES AT PHILLIPS LANDING PH 02

9233 Southern Breeze Dr, ORLANDO

6 Beds 7 Baths 6,346 SqFt Single Family Residence MLS® # O6326422
Active 8966 Easterling Dr, ORLANDO

$3,899,995

▼ $100,000 BAY HILL SEC 05

8966 Easterling Dr, ORLANDO

4 Beds 5 Baths 3,987 SqFt Single Family Residence MLS® # O6279143
Active 811 N Lake Adair Blvd, ORLANDO

$3,850,000

▼ $148,000 HOFFMAN TERRACE

811 N Lake Adair Blvd, ORLANDO

5 Beds 6 Baths 7,795 SqFt Single Family Residence MLS® # O6333890
Active 4575 New Broad St, ORLANDO

$3,794,000

BALDWIN PARK UT 01 50 121

4575 New Broad St, ORLANDO

4 Beds 8 Baths 6,138 SqFt Single Family Residence MLS® # O6352208
Active 10339 Hart Branch Cir, ORLANDO

$3,695,000

NORTH SHORE AT LAKE HART PRCL 04

10339 Hart Branch Cir, ORLANDO

5 Beds 5 Baths 5,139 SqFt Single Family Residence MLS® # O6334835
Active 9131 Santorini Dr, ORLANDO

$3,580,000

LAUREL POINTE PH 1

9131 Santorini Dr, ORLANDO

6 Beds 7 Baths 6,672 SqFt Single Family Residence MLS® # O6336142
Active 11205 Tindall Rd, ORLANDO

$3,500,000

N/A

11205 Tindall Rd, ORLANDO

2 Beds 3 Baths 3,859 SqFt Single Family Residence MLS® # O6351161
Active 10300 Pocket Ln, ORLANDO

$3,500,000

▼ $250,000 WILLIS R MUNGERS LAND SUB

10300 Pocket Ln, ORLANDO

5 Beds 5 Baths 6,446 SqFt Single Family Residence MLS® # O6319089
Active 10300 Pocket Ln, ORLANDO

$3,500,000

▼ $250,000 WILLIS R MUNGERS LAND SUB

10300 Pocket Ln, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6320092
Active 7017 Via Carmel Way, ORLANDO

$3,499,000

▼ $491,000 CARMEL

7017 Via Carmel Way, ORLANDO

5 Beds 6 Baths 6,202 SqFt Single Family Residence MLS® # O6276258

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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