City: Celebration | ChampionsGate | Clermont | Davenport | Haines City | Kissimmee | Lake Buena Vista | Orlando | Reunion | Windermere | Winter Garden
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!
Search Orlando Real Estate Listings
Click the links below to sort results by price range.
-
All Listings
-
Under $100,000
-
$100,000 - $200,000
-
$200,000 - $300,000
-
$300,000 - $400,000
-
$400,000 - $500,000
-
$500,000 - $600,000
-
$600,000 - $700,000
-
$700,000 - $800,000
-
$800,000 - $900,000
-
$900,000 - $1,000,000
-
Over $1,000,000
New
FEATURED
Active
$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
$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
$899,950
▼ $75,050
TURNBURY WOODS
5310 Faywood Ct, ORLANDO
4
Beds
3
Baths
3,706 SqFt
Single Family Residence
MLS® # S5076940
FEATURED
Active
$799,950
SOLTERRA, OAKMONT
5422 Oakgrain Ct, DAVENPORT
8
Beds
6
Baths
3,380 SqFt
Single Family Residence
MLS® # S5079573
FEATURED
Active
$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
$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
$649,950
▼ $25,000
SOLTERRA, OAKMONT
4372 Acorn Ct, DAVENPORT
6
Beds
5
Baths
3,149 SqFt
Single Family Residence
MLS® # S5071100
FEATURED
Active
$579,950
▼ $20,000
WATERSONG
339 Yellow Snapdragon Dr, DAVENPORT
5
Beds
5
Baths
3,367 SqFt
Single Family Residence
MLS® # S5069805
FEATURED
Active
$550,000
▼ $100,000
HIGHLANDS RESERVE
340 Kings Way, DAVENPORT
5
Beds
4
Baths
2,677 SqFt
Single Family Residence
MLS® # S5071024
FEATURED
Active
$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
$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
$449,950
INDIAN RIDGE
7802 Indian Ridge Tr S, KISSIMMEE
4
Beds
2
Baths
1,971 SqFt
Single Family Residence
MLS® # S5079024
FEATURED
Active
$435,000
WINDSOR HILLS, VISTAS
2558 Renshaw St, KISSIMMEE
3
Beds
3
Baths
1,440 SqFt
Townhouse
MLS® # S5079795
FEATURED
Active
$429,950
▼ $20,000
HIGHLANDS RESERVE
219 Troon Cir, DAVENPORT
4
Beds
3
Baths
1,756 SqFt
Single Family Residence
MLS® # S5076560
FEATURED
Active
$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
$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
$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
$419,950
▼ $20,000
LINDFIELDS
2934 Dickens Cir, KISSIMMEE
4
Beds
3
Baths
2,210 SqFt
Single Family Residence
MLS® # S5077284
FEATURED
Active
$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
$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
$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
$299,950
REGAL PALMS
3632 Calabria Ave, DAVENPORT
4
Beds
3
Baths
1,425 SqFt
Townhouse
MLS® # S5080466
New
FEATURED
Active
$299,950
REGAL PALMS AT HIGHLAND RESERVE
615 Terra Lago St, DAVENPORT
3
Beds
3
Baths
1,457 SqFt
Townhouse
MLS® # S5080470
FEATURED
Active
$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
$272,000
VENETIAN BAY VILLAGE
4005 Santa Maria Dr 104, KISSIMMEE
3
Beds
2
Baths
1,296 SqFt
Condominium
MLS® # S5079922
FEATURED
Active
$269,950
VILLAGES AT MANGO KEY
3156 Tamarind Cir, KISSIMMEE
2
Beds
2
Baths
1,012 SqFt
Townhouse
MLS® # S5075852
FEATURED
Active
$249,950
TUSCANA
1370 Tuscana Ln 5208, DAVENPORT
3
Beds
2
Baths
1,244 SqFt
Condo - Hotel
MLS® # S5078891
FEATURED
Active
$234,950
TUSCANA
1361 Tuscan Ter 7207, DAVENPORT
2
Beds
2
Baths
1,134 SqFt
Condominium
MLS® # S5071081
FEATURED
Active
$229,950
▼ $20,000
TUSCANA
1370 Tuscana Ln 5407, DAVENPORT
2
Beds
2
Baths
1,134 SqFt
Condominium
MLS® # S5072326
FEATURED
Active
$227,000
▼ $15,000
BAHAMA BAY
313 Lucaya Loop B5/u313, DAVENPORT
3
Beds
2
Baths
1,655 SqFt
Condominium
MLS® # S5076628
FEATURED
Active
$174,950
▼ $10,050
ENCLAVE AT ORLANDO
6165 Carrier Dr 1303, ORLANDO
2
Beds
2
Baths
583 SqFt
Condo - Hotel
MLS® # S5072832
FEATURED
Active
$125,000
▼ $14,950
ENCLAVE AT ORLANDO
6165 Carrier Dr 3412, ORLANDO
1
Bed
1
Bath
408 SqFt
Condo - Hotel
MLS® # S5077721
New
Active
$999,750,000
OVERSTREET CRATE
1211 East Maple St, WINTER GARDEN
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6089031
Active
$27,700,000
Mountain Lake Cut Off Rd, LAKE WALES
0
Beds
0
Baths
0 SqFt
Land
MLS® # P4922237
Active
$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
$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
$23,300,000
▲ $5,300,000
GOODWINS ADD
110 West Jefferson St, ORLANDO
0
Beds
0
Baths
0 SqFt
Land
MLS® # OM650214
Active
$15,986,000
TWELVE OAKS
1220 North Park Ave, WINTER PARK
7
Beds
7
Baths
12,475 SqFt
Single Family Residence
MLS® # O6012672
Active
$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
$14,000,000
Royal Oak Dr, LADY LAKE
0
Beds
0
Baths
0 SqFt
Land
MLS® # G5052628
Active
$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
$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
$10,500,000
Wolf Branch Rd, MOUNT DORA
0
Beds
0
Baths
0 SqFt
Land
MLS® # G5063435
Active
$10,500,000
WEBSTER & OMOHUNDRO SUB
4206 Knights Station Rd, LAKELAND
0
Beds
0
Baths
0 SqFt
Land
MLS® # L4929492
Active
$10,000,000
ACREAGE & UNREC
Clark St, LEESBURG
0
Beds
0
Baths
0 SqFt
Land
MLS® # O6024378
Active
$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
$9,650,000
REUNION WEST VLGS NORTH
350 Muirfield Loop, REUNION
12
Beds
14
Baths
12,962 SqFt
Single Family Residence
MLS® # O6064799
Active
$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:
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
^ Back to: Orlando Real Estate
