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Orlando Vacation Homes for Sale

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 13427 Blue Heron Beach Dr 303, ORLANDO

$375,000

BLUE HERON BEACH RESORT

13427 Blue Heron Beach Dr 303, ORLANDO

2 Beds 2 Baths 1,165 SqFt Condo - Hotel MLS® # S5091415
FEATURED
Active 12521 Floridays Resort Drive 505-f, ORLANDO

$249,000

▼ $10,950 FLORIDAYS

12521 Floridays Resort Drive 505-f, ORLANDO

2 Beds 2 Baths 957 SqFt Condo - Hotel MLS® # S5086964
FEATURED
Active 8000 Poinciana Blvd 2512, ORLANDO

$199,950

▼ $10,000 LAKE BUENA VISTA RESORT VILLAGE

8000 Poinciana Blvd 2512, ORLANDO

3 Beds 2 Baths 1,231 SqFt Condo - Hotel MLS® # S5088160
FEATURED
Active 6402 Parc Corniche Dr 5309, ORLANDO

$104,995

▼ $5 PARC CORNICHE

6402 Parc Corniche Dr 5309, ORLANDO

1 Bed 1 Bath 550 SqFt Condominium MLS® # S5089488
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 10242 Summer Meadow Way, ORLANDO

$19,000,000

GOLDEN OAK PHASE 3

10242 Summer Meadow Way, ORLANDO

7 Beds 10 Baths 9,254 SqFt Single Family Residence MLS® # O6101583
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 9200 Bentley Park Cir, ORLANDO

$12,888,000

▼ $2,112,000 BENTLEY PARK 2ND REP

9200 Bentley Park Cir, ORLANDO

7 Beds 12 Baths 20,690 SqFt Single Family Residence MLS® # L4930944
New
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 International Dr, ORLANDO

$8,112,500

WILLIS R MUNGERS LAND SUB

International Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5557835
Active 9086 Mayfair Pointe Dr, ORLANDO

$6,950,000

▼ $2,350,000 LAKE NONA ESTATES

9086 Mayfair Pointe Dr, ORLANDO

5 Beds 10 Baths 8,245 SqFt Single Family Residence MLS® # O6109126
Active 5550 Osprey Isle Ln, ORLANDO

$6,475,000

▼ $20,000 ISLE OF OSPREY

5550 Osprey Isle Ln, ORLANDO

5 Beds 6 Baths 6,730 SqFt Single Family Residence MLS® # O6115072
Active 6440 Canada Ave, ORLANDO

$6,000,000

INTERNATIONAL COVE

6440 Canada Ave, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5347857
Active 5619 Emerson Pointe Way, ORLANDO

$5,950,000

▼ $500,000 EMERSON POINTE

5619 Emerson Pointe Way, ORLANDO

4 Beds 7 Baths 7,602 SqFt Single Family Residence MLS® # O6119048
Active 9580 Sloane St, ORLANDO

$5,495,000

LAKE NONA ESTATES

9580 Sloane St, ORLANDO

5 Beds 6 Baths 8,263 SqFt Single Family Residence MLS® # O6133244
Active 13395 Kirby Smith Rd, ORLANDO

$5,250,000

NONE

13395 Kirby Smith Rd, ORLANDO

4 Beds 5 Baths 7,058 SqFt Single Family Residence MLS® # O6128450
Active 2709, 2505 Holden Ave, ORLANDO

$5,000,000

2709, 2505 Holden Ave, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6134719
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 5727 Emerington Cres, ORLANDO

$4,450,000

▼ $300,000 EMERSON POINTE

5727 Emerington Cres, ORLANDO

5 Beds 7 Baths 7,466 SqFt Single Family Residence MLS® # O6125122
Active 5733 Emerington Cres, ORLANDO

$4,350,000

▼ $400,000 EMERSON POINTE

5733 Emerington Cres, ORLANDO

5 Beds 6 Baths 7,621 SqFt Single Family Residence MLS® # O6125231
Active 3412 Oranole Rd, ORLANDO

$4,250,000

3412 Oranole Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # V4931722
Active 7466 Vivian Ln, ORLANDO

$4,250,000

NA

7466 Vivian Ln, ORLANDO

1 Bed 1 Bath 936 SqFt Single Family Residence MLS® # O6121676
Active 10330 Wittenberg Way, ORLANDO

$4,250,000

▼ $549,900 MOSS PARK RESERVE

10330 Wittenberg Way, ORLANDO

6 Beds 8 Baths 9,272 SqFt Single Family Residence MLS® # O6029473
Active 1453 Holden Ave, ORLANDO

$4,200,000

▲ $400,000 ORANGE BLOSSOM SHOPPING CENTER

1453 Holden Ave, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6051150
New
Active 6108 Dartmoor Ct, ORLANDO

$4,125,000

BAY HILL SEC 01

6108 Dartmoor Ct, ORLANDO

5 Beds 6 Baths 4,936 SqFt Single Family Residence MLS® # O6142336
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

$3,975,000

LAKE NONA ESTATES

8545 Lake Nona Shore Dr, ORLANDO

5 Beds 7 Baths 6,484 SqFt Single Family Residence MLS® # O6120079
Active 10245 Trout Rd, ORLANDO

$3,950,000

CYPRESS SHORES

10245 Trout Rd, ORLANDO

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

$3,950,000

CYPRESS SHORES

10245 Trout Rd, ORLANDO

3 Beds 2 Baths 1,440 SqFt Single Family Residence MLS® # O6111899
Active 3207 Middlesex Rd, ORLANDO

$3,695,000

BEVERLY SHORES

3207 Middlesex Rd, ORLANDO

5 Beds 7 Baths 4,944 SqFt Single Family Residence MLS® # O6134396
Active 9818 Covent Garden Dr, ORLANDO

$3,695,000

LAKE NONA ESTATES

9818 Covent Garden Dr, ORLANDO

4 Beds 6 Baths 5,646 SqFt Single Family Residence MLS® # O6108632
Active 8044 Firenze Blvd, ORLANDO

$3,500,000

VIZCAYA PH 01 45/29

8044 Firenze Blvd, ORLANDO

7 Beds 9 Baths 7,005 SqFt Single Family Residence MLS® # O6129777
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 6747 Whispering Pines Rd, ORLANDO

$3,495,000

ORLANDO-KISSIMMEE FARMS

6747 Whispering Pines Rd, ORLANDO

5 Beds 3 Baths 3,858 SqFt Single Family Residence MLS® # T3462179
Active 8959 Bay Cove Ct, ORLANDO

$3,495,000

▲ $195,000 BAY HILL SEC 04

8959 Bay Cove Ct, ORLANDO

3 Beds 4 Baths 5,201 SqFt Single Family Residence MLS® # O6123585
Active 17201 East Colonial Dr, ORLANDO

$3,400,000

▼ $400,000

17201 East Colonial Dr, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6129048
Active 10109 Tavistock Rd, ORLANDO

$3,295,000

LAKE NONA ESTATES

10109 Tavistock Rd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6097146
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 9718 Kilgore Rd, ORLANDO

$3,199,000

ACREAGE

9718 Kilgore Rd, ORLANDO

5 Beds 4 Baths 4,321 SqFt Single Family Residence MLS® # O6141295
Active 9123 Santorini Dr, ORLANDO

$3,083,995

▲ $58,000 LAUREL POINTE LAKE NONA

9123 Santorini Dr, ORLANDO

5 Beds 6 Baths 6,572 SqFt Single Family Residence MLS® # O6086682
Active 20720 Sabal St, ORLANDO

$3,000,000

N/A

20720 Sabal St, ORLANDO

6 Beds 8 Baths 6,000 SqFt Single Family Residence MLS® # O6124597
Active Sr 520, Orlando, Fl.32833 State Rd 520, ORLANDO

$3,000,000

▲ $300,000 EAST O.C. S OF S.R.50

Sr 520, Orlando, Fl.32833 State Rd 520, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O5915638
Active 8649 Amber Oak Ct, ORLANDO

$2,999,900

FOREST LAKES PH 02

8649 Amber Oak Ct, ORLANDO

5 Beds 6 Baths 6,246 SqFt Single Family Residence MLS® # O6140076
Active 1427 North Semoran Blvd, ORLANDO

$2,995,000

LEAWOOD

1427 North Semoran Blvd, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # O6089209
Active 9000 Shawn Park Pl, ORLANDO

$2,980,000

SOUTH BAY VILLAS

9000 Shawn Park Pl, ORLANDO

6 Beds 5 Baths 5,071 SqFt Single Family Residence MLS® # O6135433
Active 8125 Via Rosa, ORLANDO

$2,969,000

MIRABELLA/VIZCAYA PH 03

8125 Via Rosa, ORLANDO

4 Beds 5 Baths 4,592 SqFt Single Family Residence MLS® # O6140907
Active 13782 Rosbash Alley, ORLANDO

$2,950,000

LAUREATE PARK PH 10

13782 Rosbash Alley, ORLANDO

3 Beds 7 Baths 4,674 SqFt Single Family Residence MLS® # O6083753

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:

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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