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Kissimmee VACATION HOMES FOR SALE

City:  Celebration | ChampionsGate | Clermont | Davenport | Haines City | Kissimmee | Lake Buena Vista | Orlando | Reunion |  Windermere | Winter Garden

Kissimmee ResortsBella Vida Resort -  Caribe Cove ResortEmbassy Suites At Sunset Walk - Emerald Island Resort - Encantada - Encore Club at Reunion - Fiesta KeyFormosa ValleyLake Berkley - Lucaya Village - Magic Village - Margaritaville Resort OrlandoParadise PalmsRegal OaksSolara ResortStorey Lake Resort - Summerville Resort - Terra Verde ResortVenetian Bay - Veranda Palms - Villas At Seven Dwarfs LaneWindsor Hills ResortWindsor Palms Resort

What do the popular theme parks Walt Disney World, Universal Orlando and Sea World have in common? They’re located right next door to Kissimmee, Florida. The city is located just outside Orlando in Osceola County, and is one of the fastest growing communities in Florida.

Kissimmee is a family-friendly community that is not only a great place to visit, but a better place to call home. Many people who visit from cold weather states like Michigan and New York, as well as frequent travelers from Canada and Europe, find Kissimmee so appealing that they buy second homes here. It’s no wonder because Kissimmee vacation homes offer great access to a thriving downtown district and a high level of municipal services.

Check out the available Kissimmee vacation real estate below, or continue reading to learn more about the many wonderful holiday communities found in the city!

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FEATURED
Active W Irlo Bronson Memorial Hwy, KISSIMMEE

$13,700,000

ACREAGE & UNREC

W Irlo Bronson Memorial Hwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land Land MLS® # S5085096
FEATURED
Active 200 N Hoagland Blvd, KISSIMMEE

$7,700,000

ACREAGE & UNREC

200 N Hoagland Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land Land MLS® # S5085102
FEATURED
Active 7936 Jacks Club Ct, KISSIMMEE

$1,725,000

▼ $125,000 REUNION, BEARS DEN, REUNION WEST

7936 Jacks Club Ct, KISSIMMEE

6 Beds 7 Baths 4,588 SqFt Residential Single Family Residence MLS® # S5144037
FEATURED
Active 262 Marcello Blvd, KISSIMMEE

$899,999

BELLAVIDA RESORT

262 Marcello Blvd, KISSIMMEE

12 Beds 12 Baths 4,762 SqFt Residential Single Family Residence MLS® # S5146865
FEATURED
Active 1636 Nassau Point Tr, KISSIMMEE

$815,000

SOLARA RESORT

1636 Nassau Point Tr, KISSIMMEE

9 Beds 7 Baths 4,828 SqFt Residential Single Family Residence MLS® # S5138722
FEATURED
Active 8019 Knee Deep Rd, KISSIMMEE

$724,500

MARGARITAVILLE RESORT, ROLLING OAKS

8019 Knee Deep Rd, KISSIMMEE

5 Beds 4 Baths 1,908 SqFt Residential Single Family Residence MLS® # S5149245
FEATURED
Active 350 Pendant Ct, KISSIMMEE

$719,950

ENCORE AT REUNION, REUNION WEST

350 Pendant Ct, KISSIMMEE

8 Beds 7 Baths 3,412 SqFt Residential Single Family Residence MLS® # S5120062
FEATURED
Active 551 Lasso Dr, KISSIMMEE

$699,999

ENCORE AT REUNION, REUNION WEST

551 Lasso Dr, KISSIMMEE

8 Beds 7 Baths 3,401 SqFt Residential Single Family Residence MLS® # S5128532
FEATURED
Active 7527 Marker Ave, KISSIMMEE

$699,999

ENCORE AT REUNION, REUNION WEST

7527 Marker Ave, KISSIMMEE

8 Beds 6 Baths 3,612 SqFt Residential Single Family Residence MLS® # S5126948
FEATURED
Active 7541 Marker Ave, KISSIMMEE

$669,456

ENCORE AT REUNION, REUNION WEST

7541 Marker Ave, KISSIMMEE

8 Beds 7 Baths 3,412 SqFt Residential Single Family Residence MLS® # S5128347
FEATURED
Active 331 Pendant Ct, KISSIMMEE

$669,123

ENCORE AT REUNION, REUNION WEST

331 Pendant Ct, KISSIMMEE

8 Beds 7 Baths 3,412 SqFt Residential Single Family Residence MLS® # S5128341
FEATURED
Active 7613 Brookhurst Ln, KISSIMMEE

$649,000

▼ $20,789 ENCORE AT REUNION, REUNION WEST

7613 Brookhurst Ln, KISSIMMEE

8 Beds 7 Baths 3,412 SqFt Residential Single Family Residence MLS® # S5128335
FEATURED
Active 2691 La Isla Ct, KISSIMMEE

$539,000

EMERALD ISLAND RESORT

2691 La Isla Ct, KISSIMMEE

7 Beds 5 Baths 2,793 SqFt Residential Single Family Residence MLS® # S5142120
New FEATURED
Active 276 Southfield St, KISSIMMEE

$535,000

ENCORE AT REUNION, REUNION WEST

276 Southfield St, KISSIMMEE

4 Beds 3 Baths 2,363 SqFt Residential Single Family Residence MLS® # S5150128
FEATURED
Active 8550 Sunrise Key Dr, KISSIMMEE

$529,999

EMERALD ISLAND RESORT

8550 Sunrise Key Dr, KISSIMMEE

7 Beds 5 Baths 2,881 SqFt Residential Single Family Residence MLS® # S5148879
FEATURED
Active 2685 Oneida Loop, KISSIMMEE

$525,000

INDIAN CREEK

2685 Oneida Loop, KISSIMMEE

5 Beds 4 Baths 2,136 SqFt Residential Single Family Residence MLS® # S5128631
New FEATURED
Active 2694 La Isla Ct, KISSIMMEE

$520,000

EMERALD ISLAND RESORT

2694 La Isla Ct, KISSIMMEE

5 Beds 3 Baths 2,317 SqFt Residential Single Family Residence MLS® # S5149891
FEATURED
Active 3151 Sunset Walk Dr 1110, KISSIMMEE

$479,999

SUNSET WALK HOTEL, EMBASSY SUITES

3151 Sunset Walk Dr 1110, KISSIMMEE

2 Beds 2 Baths 1,029 SqFt Residential Condo - Hotel MLS® # S5141654
FEATURED
Active 8965 Cuban Palm Rd, KISSIMMEE

$479,000

PARADISE PALMS RESORT

8965 Cuban Palm Rd, KISSIMMEE

6 Beds 5 Baths 3,291 SqFt Residential Single Family Residence MLS® # S5147422
FEATURED
Active 4661 Golden Beach Ct, KISSIMMEE

$475,000

TERRA VERDE

4661 Golden Beach Ct, KISSIMMEE

5 Beds 3 Baths 2,269 SqFt Residential Single Family Residence MLS® # S5142740
FEATURED
Active 4805 Brier Rose Ln, KISSIMMEE

$464,900

STOREY LAKE RESORT

4805 Brier Rose Ln, KISSIMMEE

4 Beds 3 Baths 1,914 SqFt Residential Townhouse MLS® # S5132665
FEATURED
Active 2901 Sunset Vista Ct, KISSIMMEE

$459,999

▼ $20,001 SUNSET LAKES

2901 Sunset Vista Ct, KISSIMMEE

4 Beds 2 Baths 1,728 SqFt Residential Single Family Residence MLS® # S5143231
FEATURED
Active 3151 Sunset Walk Dr 1108, KISSIMMEE

$449,999

▼ $50,000 EMBASSY SUITES, SUNSET WALK HOTEL

3151 Sunset Walk Dr 1108, KISSIMMEE

2 Beds 2 Baths 1,029 SqFt Residential Condo - Hotel MLS® # S5132617
FEATURED
Active 1909 Majorca Dr, KISSIMMEE

$445,000

WINDSOR AT WESTSIDE

1909 Majorca Dr, KISSIMMEE

5 Beds 5 Baths 2,263 SqFt Residential Townhouse MLS® # S5149758
FEATURED
Active 2427 Dubai St, KISSIMMEE

$444,000

▼ $20,000 WINDSOR AT WESTSIDE

2427 Dubai St, KISSIMMEE

5 Beds 5 Baths 2,265 SqFt Residential Townhouse MLS® # S5123971
FEATURED
Active 3015 Yellow Lantana Ln, KISSIMMEE

$418,999

ENCANTADA

3015 Yellow Lantana Ln, KISSIMMEE

4 Beds 3 Baths 1,636 SqFt Residential Townhouse MLS® # S5126724
FEATURED
Active 8059 Knee Deep Rd, KISSIMMEE

$410,000

MARGARITAVILLE RESORT, ROLLING OAKS

8059 Knee Deep Rd, KISSIMMEE

3 Beds 3 Baths 1,410 SqFt Residential Single Family Residence MLS® # S5148481
FEATURED
Active 3151 Sunset Walk Dr 1214, KISSIMMEE

$399,000

▼ $50,000 SUNSET WALK HOTEL, EMBASSY SUITES

3151 Sunset Walk Dr 1214, KISSIMMEE

2 Beds 2 Baths 1,163 SqFt Residential Condo - Hotel MLS® # S5141552
FEATURED
Active 8070 Unwind Way 5416, KISSIMMEE

$377,900

▼ $71,100 SUNSET WALK HOTEL, EMBASSY SUITES

8070 Unwind Way 5416, KISSIMMEE

2 Beds 2 Baths 1,029 SqFt Residential Condo - Hotel MLS® # S5141228
New FEATURED
Active 2916 On The Rocks Pt, KISSIMMEE

$369,999

MARGARITAVILLE, ROLLING OAKS

2916 On The Rocks Pt, KISSIMMEE

3 Beds 3 Baths 1,545 SqFt Residential Townhouse MLS® # S5149980
FEATURED
Active 197 Hideaway Beach Ln, KISSIMMEE

$355,000

▼ $24,000 TERRA VERDE

197 Hideaway Beach Ln, KISSIMMEE

4 Beds 2 Baths 1,542 SqFt Residential Single Family Residence MLS® # S5139158
FEATURED
Active 2821 Almaton Loop 203, KISSIMMEE

$349,900

WINDSOR HILLS, VENTURA AT WINDSOR HILLS

2821 Almaton Loop 203, KISSIMMEE

3 Beds 2 Baths 1,246 SqFt Residential Condominium MLS® # S5147977
FEATURED
Active 8061 Vacation Ave 2508, KISSIMMEE

$349,000

▼ $50,999 SUNSET WALK HOTEL, EMBASSY SUITES

8061 Vacation Ave 2508, KISSIMMEE

2 Beds 2 Baths 1,029 SqFt Residential Condo - Hotel MLS® # S5144118
FEATURED
Active 8061 Vacation Ave 510, KISSIMMEE

$345,000

▼ $54,999 SUNSET WALK HOTEL, EMBASSY SUITES

8061 Vacation Ave 510, KISSIMMEE

2 Beds 2 Baths 1,029 SqFt Residential Condo - Hotel MLS® # S5144575
FEATURED
Active 8957 Sugar Palm Rd, KISSIMMEE

$344,000

▼ $5,000 PARADISE PALMS RESORT

8957 Sugar Palm Rd, KISSIMMEE

4 Beds 3 Baths 1,902 SqFt Residential Townhouse MLS® # S5142216
FEATURED
Active 3083 Yellow Lantana Ln, KISSIMMEE

$339,000

▼ $31,000 ENCANTADA

3083 Yellow Lantana Ln, KISSIMMEE

4 Beds 3 Baths 1,340 SqFt Residential Townhouse MLS® # S5116892
FEATURED
Active 3222 Cupid Pl, KISSIMMEE

$319,500

▼ $12,500 WEST LUCAYA VILLAGE

3222 Cupid Pl, KISSIMMEE

4 Beds 3 Baths 1,694 SqFt Residential Townhouse MLS® # S5141535
FEATURED
Active 2200 San Zanobi Dr 108, KISSIMMEE

$310,000

VENETIAN BAY

2200 San Zanobi Dr 108, KISSIMMEE

4 Beds 3 Baths 1,470 SqFt Residential Condominium MLS® # S5102991
FEATURED
Active 2809 Almaton Loop 401, KISSIMMEE

$305,000

▼ $12,000 VENTURA AT WINDSOR HILLS, WINDSOR HILLS

2809 Almaton Loop 401, KISSIMMEE

3 Beds 2 Baths 1,246 SqFt Residential Condominium MLS® # S5147712
FEATURED
Active 2841 Oakwater Dr, KISSIMMEE

$299,999

▼ $19,001 OAKWATER

2841 Oakwater Dr, KISSIMMEE

3 Beds 2 Baths 1,427 SqFt Residential Condominium MLS® # S5138853
FEATURED
Active 3151 Sunset Walk Dr 1209, KISSIMMEE

$298,999

EMBASSY SUITES, SUNSET WALK HOTEL

3151 Sunset Walk Dr 1209, KISSIMMEE

1 Bed 1 Bath 734 SqFt Residential Condo - Hotel MLS® # S5146573
FEATURED
Active 5108 Dominica Dr, KISSIMMEE

$290,000

COMPASS BAY

5108 Dominica Dr, KISSIMMEE

3 Beds 3 Baths 1,394 SqFt Residential Townhouse MLS® # S5146885
FEATURED
Active 7671 Comrow St 202, KISSIMMEE

$289,950

WINDSOR HILLS, VENTURA AT WINDSOR HILLS

7671 Comrow St 202, KISSIMMEE

2 Beds 2 Baths 1,081 SqFt Residential Condominium MLS® # S5111171
FEATURED
Active 4600 Yellowgold Rd W 105, KISSIMMEE

$280,000

▲ $10,250 VILLAS AT SEVEN DWARFS LANE

4600 Yellowgold Rd W 105, KISSIMMEE

3 Beds 2 Baths 1,296 SqFt Residential Condominium MLS® # S5139139
FEATURED
Active 3151 Sunset Walk Dr 1202, KISSIMMEE

$280,000

▼ $19,999 EMBASSY SUITES, SUNSET WALK HOTEL

3151 Sunset Walk Dr 1202, KISSIMMEE

1 Bed 1 Bath 745 SqFt Residential Condo - Hotel MLS® # S5137800
FEATURED
Active 8070 Unwind Way 5314, KISSIMMEE

$279,900

▼ $69,099 SUNSET WALK HOTEL, EMBASSY SUITES

8070 Unwind Way 5314, KISSIMMEE

1 Bed 1 Bath 745 SqFt Residential Condo - Hotel MLS® # S5141241
FEATURED
Active 8061 Vacation Ave 2313, KISSIMMEE

$275,000

SUNSET WALK HOTEL, EMBASSY SUITES

8061 Vacation Ave 2313, KISSIMMEE

1 Bed 1 Bath 501 SqFt Residential Condo - Hotel MLS® # S5141339
FEATURED
Active 8061 Vacation Ave 2307, KISSIMMEE

$275,000

SUNSET WALK HOTEL, EMBASSY SUITES

8061 Vacation Ave 2307, KISSIMMEE

1 Bed 1 Bath 501 SqFt Residential Condo - Hotel MLS® # S5141325

The Kissimmee Community

The city’s unusual name is said to be the modern spelling of a tribal word from one of Florida’s lesser-known tribes, the Jororo. A 1752 Spanish map used the name “Cacema,” which has evolved into today’s spelling of Kissimmee.

In the early to mid-20th century, Kissimmee’s economy was based on cattle, citrus and other crops. Retirees were encouraged to move here in the 1950’s. Kissimmee real estate really took off after Walt Disney World was built in the 1970’s. Since then, other theme parks and attractions followed, such as Fun Spot America, Gatorland, Kissimmee Air Museum, as well as several dinner theaters and miniature golf parks.

Kissimmee Real Estate Market

Kissimmee vacation home buyers also choose the city because of the wide range of parks and recreational activities that are available, including Lake Tohopekaliga, which offers some of the best bass fishing in the world.

Nature lovers can enjoy a thrilling airboat ride and discover a world alive with tropical birds, turtles and alligators. There are plenty of championship golf courses nearby that are ideal for the beginner or professional golfer. And you’ll find a mix of dining options and unique shopping venues in the area too.

Communities in Kissimmee, Florida


One reason people buy Kissimmee vacation real estate as a second home is to generate income by renting out the property to visitors. If you’d like more information about the homes for sale in Kissimmee that can be rented as a vacation property, please contact a Team Donovan agent online today or call 407-705-2616.

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