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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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New FEATURED
Active 915 Golden Bear Dr, REUNION

$1,299,950

REUNION, MASTERS LANDING, REUNION WEST VLGS NORTH

915 Golden Bear Dr, REUNION

5 Beds 6 Baths 3,406 SqFt Single Family Residence MLS® # S5080135
FEATURED
Active 631 Lasso Dr, KISSIMMEE

$985,000

▼ $65,000 ENCORE AT REUNION, REUNION WEST

631 Lasso Dr, KISSIMMEE

10 Beds 10 Baths 4,724 SqFt Single Family Residence MLS® # S5072544
FEATURED
Active 5310 Faywood Ct, ORLANDO

$899,950

▼ $75,050 TURNBURY WOODS

5310 Faywood Ct, ORLANDO

4 Beds 3 Baths 3,706 SqFt Single Family Residence MLS® # S5076940
FEATURED
Active 5422 Oakgrain Ct, DAVENPORT

$799,950

SOLTERRA, OAKMONT

5422 Oakgrain Ct, DAVENPORT

8 Beds 6 Baths 3,380 SqFt Single Family Residence MLS® # S5079573
FEATURED
Active 601 Lasso Dr, KISSIMMEE

$779,950

ENCORE AT REUNION, REUNION WEST

601 Lasso Dr, KISSIMMEE

6 Beds 7 Baths 3,099 SqFt Single Family Residence MLS® # S5079651
FEATURED
Active 7412 Soiree Way, REUNION

$775,000

▼ $74,950 REUNION RESORT, HOMESTEAD

7412 Soiree Way, REUNION

5 Beds 4 Baths 2,764 SqFt Single Family Residence MLS® # S5074775
FEATURED
Active 4372 Acorn Ct, DAVENPORT

$649,950

▼ $25,000 SOLTERRA, OAKMONT

4372 Acorn Ct, DAVENPORT

6 Beds 5 Baths 3,149 SqFt Single Family Residence MLS® # S5071100
FEATURED
Active 339 Yellow Snapdragon Dr, DAVENPORT

$579,950

▼ $20,000 WATERSONG

339 Yellow Snapdragon Dr, DAVENPORT

5 Beds 5 Baths 3,367 SqFt Single Family Residence MLS® # S5069805
FEATURED
Active 340 Kings Way, DAVENPORT

$550,000

▼ $100,000 HIGHLANDS RESERVE

340 Kings Way, DAVENPORT

5 Beds 4 Baths 2,677 SqFt Single Family Residence MLS® # S5071024
FEATURED
Active 2513 Calla Lily Cv, KISSIMMEE

$534,950

CRESCENT LAKES, CALLA LILY COVE

2513 Calla Lily Cv, KISSIMMEE

7 Beds 3 Baths 2,679 SqFt Single Family Residence MLS® # S5076964
FEATURED
Active 546 Windsor Pl, DAVENPORT

$499,900

▼ $50 ABBEY AT WEST HAVEN

546 Windsor Pl, DAVENPORT

5 Beds 6 Baths 2,493 SqFt Single Family Residence MLS® # S5071619
FEATURED
Active 7802 Indian Ridge Tr S, KISSIMMEE

$449,950

INDIAN RIDGE

7802 Indian Ridge Tr S, KISSIMMEE

4 Beds 2 Baths 1,971 SqFt Single Family Residence MLS® # S5079024
FEATURED
Active 2558 Renshaw St, KISSIMMEE

$435,000

WINDSOR HILLS, VISTAS

2558 Renshaw St, KISSIMMEE

3 Beds 3 Baths 1,440 SqFt Townhouse MLS® # S5079795
FEATURED
Active 219 Troon Cir, DAVENPORT

$429,950

▼ $20,000 HIGHLANDS RESERVE

219 Troon Cir, DAVENPORT

4 Beds 3 Baths 1,756 SqFt Single Family Residence MLS® # S5076560
FEATURED
Active 8422 Secret Key Cv, KISSIMMEE

$424,950

▼ $5,045 EMERALD ISLAND RESORT

8422 Secret Key Cv, KISSIMMEE

4 Beds 2 Baths 1,960 SqFt Single Family Residence MLS® # S5074673
FEATURED
Active 155 Barefoot Beach Way, KISSIMMEE

$419,950

▼ $30,000 TERRA VERDE

155 Barefoot Beach Way, KISSIMMEE

4 Beds 2 Baths 1,940 SqFt Single Family Residence MLS® # S5075650
FEATURED
Active 723 Old Bridge Cir, DAVENPORT

$419,950

▼ $30,000 WEST STONEBRIDGE

723 Old Bridge Cir, DAVENPORT

4 Beds 3 Baths 1,944 SqFt Single Family Residence MLS® # S5076363
FEATURED
Active 2934 Dickens Cir, KISSIMMEE

$419,950

▼ $20,000 LINDFIELDS

2934 Dickens Cir, KISSIMMEE

4 Beds 3 Baths 2,210 SqFt Single Family Residence MLS® # S5077284
FEATURED
Active 2418 Willow Tree Ln, KISSIMMEE

$349,950

CRESCENT LAKES, WILLOW BEND

2418 Willow Tree Ln, KISSIMMEE

3 Beds 2 Baths 1,386 SqFt Single Family Residence MLS® # S5078493
New FEATURED
Active 7603 Heritage Crossing Way 202, REUNION

$339,950

▲ $5,000 HERITAGE CROSSING, REUNION

7603 Heritage Crossing Way 202, REUNION

3 Beds 2 Baths 1,344 SqFt Condominium MLS® # S5080456
FEATURED
Active 199 Ronda Ct, DAVENPORT

$334,950

▼ $15,000 LOMA LINDA

199 Ronda Ct, DAVENPORT

4 Beds 2 Baths 1,663 SqFt Single Family Residence MLS® # S5076605
New FEATURED
Active 3632 Calabria Ave, DAVENPORT

$299,950

REGAL PALMS

3632 Calabria Ave, DAVENPORT

4 Beds 3 Baths 1,425 SqFt Townhouse MLS® # S5080466
New FEATURED
Active 615 Terra Lago St, DAVENPORT

$299,950

REGAL PALMS AT HIGHLAND RESERVE

615 Terra Lago St, DAVENPORT

3 Beds 3 Baths 1,457 SqFt Townhouse MLS® # S5080470
FEATURED
Active 616 Calabria Ave, DAVENPORT

$279,950

▼ $40,000 REGAL PALMS AT HIGHLAND RESERVE

616 Calabria Ave, DAVENPORT

4 Beds 3 Baths 1,492 SqFt Townhouse MLS® # S5072280
FEATURED
Active 4005 Santa Maria Dr 104, KISSIMMEE

$272,000

VENETIAN BAY VILLAGE

4005 Santa Maria Dr 104, KISSIMMEE

3 Beds 2 Baths 1,296 SqFt Condominium MLS® # S5079922
FEATURED
Active 3156 Tamarind Cir, KISSIMMEE

$269,950

VILLAGES AT MANGO KEY

3156 Tamarind Cir, KISSIMMEE

2 Beds 2 Baths 1,012 SqFt Townhouse MLS® # S5075852
FEATURED
Active 1370 Tuscana Ln 5208, DAVENPORT

$249,950

TUSCANA

1370 Tuscana Ln 5208, DAVENPORT

3 Beds 2 Baths 1,244 SqFt Condo - Hotel MLS® # S5078891
FEATURED
Active 1361 Tuscan Ter 7207, DAVENPORT

$234,950

TUSCANA

1361 Tuscan Ter 7207, DAVENPORT

2 Beds 2 Baths 1,134 SqFt Condominium MLS® # S5071081
FEATURED
Active 1370 Tuscana Ln 5407, DAVENPORT

$229,950

▼ $20,000 TUSCANA

1370 Tuscana Ln 5407, DAVENPORT

2 Beds 2 Baths 1,134 SqFt Condominium MLS® # S5072326
FEATURED
Active 313 Lucaya Loop B5/u313, DAVENPORT

$227,000

▼ $15,000 BAHAMA BAY

313 Lucaya Loop B5/u313, DAVENPORT

3 Beds 2 Baths 1,655 SqFt Condominium MLS® # S5076628
FEATURED
Active 6165 Carrier Dr 1303, ORLANDO

$174,950

▼ $10,050 ENCLAVE AT ORLANDO

6165 Carrier Dr 1303, ORLANDO

2 Beds 2 Baths 583 SqFt Condo - Hotel MLS® # S5072832
FEATURED
Active 6165 Carrier Dr 3412, ORLANDO

$125,000

▼ $14,950 ENCLAVE AT ORLANDO

6165 Carrier Dr 3412, ORLANDO

1 Bed 1 Bath 408 SqFt Condo - Hotel MLS® # S5077721
New
Active 1211 East Maple St, WINTER GARDEN

$999,750,000

OVERSTREET CRATE

1211 East Maple St, WINTER GARDEN

0 Beds 0 Baths 0 SqFt Land MLS® # O6089031
Active Mountain Lake Cut Off Rd, LAKE WALES

$27,700,000

Mountain Lake Cut Off Rd, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # P4922237
Active 9291 Point Cypress Dr, ORLANDO

$25,000,000

CYPRESS POINT PH 02

9291 Point Cypress Dr, ORLANDO

12 Beds 15 Baths 14,706 SqFt Single Family Residence MLS® # O5965014
Active 9508 Windy Ridge Rd, WINDERMERE

$24,995,000

▼ $5,005,000 ACREAGE & UNREC

9508 Windy Ridge Rd, WINDERMERE

7 Beds 16 Baths 29,739 SqFt Single Family Residence MLS® # O6060999
Active 110 West Jefferson St, ORLANDO

$23,300,000

▲ $5,300,000 GOODWINS ADD

110 West Jefferson St, ORLANDO

0 Beds 0 Baths 0 SqFt Land MLS® # OM650214
Active 1220 North Park Ave, WINTER PARK

$15,986,000

TWELVE OAKS

1220 North Park Ave, WINTER PARK

7 Beds 7 Baths 12,475 SqFt Single Family Residence MLS® # O6012672
Active 9200 Bentley Park Cir, ORLANDO

$15,000,000

BENTLEY PARK 2ND REP

9200 Bentley Park Cir, ORLANDO

7 Beds 12 Baths 20,690 SqFt Single Family Residence MLS® # L4930944
Active Royal Oak Dr, LADY LAKE

$14,000,000

Royal Oak Dr, LADY LAKE

0 Beds 0 Baths 0 SqFt Land MLS® # G5052628
Active 10151 Enchanted Oak Dr, GOLDEN OAK

$13,995,000

▼ $500,000 GOLDEN OAK PH 1C

10151 Enchanted Oak Dr, GOLDEN OAK

7 Beds 10 Baths 10,742 SqFt Single Family Residence MLS® # O6036313
Active 11301 Bridge House Rd, WINDERMERE

$11,995,000

RESERVE AT LAKE BUTLER SOUND

11301 Bridge House Rd, WINDERMERE

5 Beds 9 Baths 9,267 SqFt Single Family Residence MLS® # O6083126
Active Wolf Branch Rd, MOUNT DORA

$10,500,000

Wolf Branch Rd, MOUNT DORA

0 Beds 0 Baths 0 SqFt Land MLS® # G5063435
Active 4206 Knights Station Rd, LAKELAND

$10,500,000

WEBSTER & OMOHUNDRO SUB

4206 Knights Station Rd, LAKELAND

0 Beds 0 Baths 0 SqFt Land MLS® # L4929492
Active Clark St, LEESBURG

$10,000,000

ACREAGE & UNREC

Clark St, LEESBURG

0 Beds 0 Baths 0 SqFt Land MLS® # O6024378
Active 1233 Castle Pines Ct, REUNION

$9,999,000

REUNION WEST VILLAGE 03A

1233 Castle Pines Ct, REUNION

10 Beds 14 Baths 11,027 SqFt Single Family Residence MLS® # O6064800
Active 350 Muirfield Loop, REUNION

$9,650,000

REUNION WEST VLGS NORTH

350 Muirfield Loop, REUNION

12 Beds 14 Baths 12,962 SqFt Single Family Residence MLS® # O6064799
Active 10030 Enchanted Oak Dr, GOLDEN OAK

$9,500,000

GOLDEN OAK PH 01C

10030 Enchanted Oak Dr, GOLDEN OAK

6 Beds 7 Baths 9,444 SqFt Single Family Residence MLS® # O6017000

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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