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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!

Search Kissimmee Real Estate Listings

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FEATURED
Active West Irlo Bronson Memorial Hwy, KISSIMMEE

$13,700,000

▼ $6,300,000 ACREAGE & UNREC

West Irlo Bronson Memorial Hwy, KISSIMMEE

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

$7,700,000

▼ $12,300,000 ACREAGE & UNREC

200 N Hoagland Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5085102
FEATURED
Active 8161 Surf St, KISSIMMEE

$1,395,000

▼ $90,000 MARGARITAVILLE, ROLLING OAKS

8161 Surf St, KISSIMMEE

5 Beds 5 Baths 3,578 SqFt Single Family Residence MLS® # S5108628
FEATURED
Active 2711 Bookmark Dr, KISSIMMEE

$919,950

STOREY LAKE, COVE AT STOREY LAKE

2711 Bookmark Dr, KISSIMMEE

9 Beds 5 Baths 4,289 SqFt Single Family Residence MLS® # S5106748
FEATURED
Active 8983 Amelia Downs Tr, KISSIMMEE

$824,950

▼ $50,000 SOLARA RESORT

8983 Amelia Downs Tr, KISSIMMEE

9 Beds 7 Baths 4,363 SqFt Single Family Residence MLS® # S5086743
FEATURED
Active 451 Lasso Dr, KISSIMMEE

$719,950

ENCORE AT REUNION, REUNION RESORT

451 Lasso Dr, KISSIMMEE

8 Beds 7 Baths 3,401 SqFt Single Family Residence MLS® # S5113342
FEATURED
Active 7562 Marker Ave, KISSIMMEE

$699,900

▼ $15,000 ENCORE AT REUNION

7562 Marker Ave, KISSIMMEE

8 Beds 7 Baths 3,412 SqFt Single Family Residence MLS® # S5100653
FEATURED
Active 7617 Brookhurst Ln, KISSIMMEE

$665,000

ENCORE AT REUNION, REUNION RESORT

7617 Brookhurst Ln, KISSIMMEE

8 Beds 7 Baths 3,412 SqFt Single Family Residence MLS® # S5113348
FEATURED
Active 368 Southfield St, KISSIMMEE

$648,950

ENCORE AT REUNION, REUNION RESORT

368 Southfield St, KISSIMMEE

4 Beds 3 Baths 2,363 SqFt Single Family Residence MLS® # S5114625
FEATURED
Active 2619 Archfeld Blvd, KISSIMMEE

$609,500

WINDSOR HILLS

2619 Archfeld Blvd, KISSIMMEE

5 Beds 5 Baths 2,297 SqFt Single Family Residence MLS® # S5114610
FEATURED
Active 2918 Salted Rim Rd, KISSIMMEE

$599,950

▼ $25,049 MARGARITAVILLE, ROLLING OAKS

2918 Salted Rim Rd, KISSIMMEE

4 Beds 3 Baths 1,410 SqFt Single Family Residence MLS® # S5106497
FEATURED
Active 2968 Salted Rim Rd, KISSIMMEE

$595,000

MARGARITAVILLE, ROLLING OAKS

2968 Salted Rim Rd, KISSIMMEE

3 Beds 4 Baths 1,818 SqFt Single Family Residence MLS® # S5076132
FEATURED
Active 3184 Caribbean Soul Dr, KISSIMMEE

$595,000

MARGARITAVILLE, ROLLING OAKS

3184 Caribbean Soul Dr, KISSIMMEE

4 Beds 3 Baths 1,712 SqFt Townhouse MLS® # S5103875
FEATURED
Active 8937 Rhodes St, KISSIMMEE

$574,500

▼ $5,450 WINDSOR AT WESTSIDE

8937 Rhodes St, KISSIMMEE

5 Beds 6 Baths 2,622 SqFt Single Family Residence MLS® # S5106825
FEATURED
Active 7953 Heritage Entrance Blvd, KISSIMMEE

$569,950

▼ $30,000 ROLLING HILLS, ROLLING HILLS ESTATES

7953 Heritage Entrance Blvd, KISSIMMEE

5 Beds 4 Baths 2,618 SqFt Single Family Residence MLS® # S5106283
FEATURED
Active 8035 Acadia Estates Ct, KISSIMMEE

$549,950

▼ $5,000 ACADIA ESTATES, WYNDHAM POINTE

8035 Acadia Estates Ct, KISSIMMEE

6 Beds 5 Baths 2,769 SqFt Single Family Residence MLS® # S5098360
FEATURED
Active 7755 Teascone Blvd, KISSIMMEE

$549,950

▼ $30,000 WINDSOR HILLS

7755 Teascone Blvd, KISSIMMEE

5 Beds 5 Baths 2,342 SqFt Single Family Residence MLS® # S5111057
FEATURED
Active 280 Pendant Ct, KISSIMMEE

$549,950

▼ $29,000 ENCORE AT REUNION, REUNION RESORT

280 Pendant Ct, KISSIMMEE

5 Beds 5 Baths 2,570 SqFt Single Family Residence MLS® # S5112064
FEATURED
Active 3044 Salted Rim Rd, KISSIMMEE

$499,950

MARGARITAVILLE, ROLLING OAKS

3044 Salted Rim Rd, KISSIMMEE

2 Beds 3 Baths 1,305 SqFt Single Family Residence MLS® # S5105327
FEATURED
Active 3087 Pirate Way, KISSIMMEE

$498,950

MARGARITAVILLE, ROLLING OAKS

3087 Pirate Way, KISSIMMEE

4 Beds 3 Baths 1,410 SqFt Single Family Residence MLS® # S5113520
FEATURED
Active 155 Barefoot Beach Way, KISSIMMEE

$449,950

▼ $15,050 TERRA VERDE

155 Barefoot Beach Way, KISSIMMEE

4 Beds 2 Baths 1,940 SqFt Single Family Residence MLS® # S5105388
FEATURED
Active 8457 Secret Key Cv, KISSIMMEE

$449,950

EMERALD ISLAND RESORT

8457 Secret Key Cv, KISSIMMEE

4 Beds 3 Baths 1,542 SqFt Single Family Residence MLS® # S5114617
FEATURED
Active 3037 Sea Plane Ln, KISSIMMEE

$439,950

MARGARITAVILLE, ROLLING OAKS

3037 Sea Plane Ln, KISSIMMEE

2 Beds 3 Baths 1,305 SqFt Single Family Residence MLS® # S5112270
FEATURED
Active 3169 Pantanal Ln, KISSIMMEE

$439,950

MAGIC VILLAGE

3169 Pantanal Ln, KISSIMMEE

3 Beds 4 Baths 2,181 SqFt Townhouse MLS® # S5114284
FEATURED
Active 7959 Magnolia Bend Ct, KISSIMMEE

$435,000

ROLLING HILLS, ROLLING HILLS ESTATES

7959 Magnolia Bend Ct, KISSIMMEE

4 Beds 3 Baths 1,975 SqFt Single Family Residence MLS® # S5111630
FEATURED
Active 2980 On The Rocks Pt, KISSIMMEE

$359,950

▼ $20,000 MARGARITAVILLE, ROLLING OAKS

2980 On The Rocks Pt, KISSIMMEE

2 Beds 3 Baths 1,394 SqFt Townhouse MLS® # S5112676
FEATURED
Active 3189 Bear Path, KISSIMMEE

$349,950

INDIAN WELLS

3189 Bear Path, KISSIMMEE

3 Beds 2 Baths 1,377 SqFt Single Family Residence MLS® # S5107403
FEATURED
Active 2778 Almaton Loop 401, KISSIMMEE

$328,950

▼ $16,050 WINDSOR HILLS, VENTURA AT WINDSOR HILLS

2778 Almaton Loop 401, KISSIMMEE

3 Beds 2 Baths 1,246 SqFt Condominium MLS® # S5110893
FEATURED
Active 2374 Caravelle Cir, KISSIMMEE

$320,000

▼ $29,950 CORAL CAY RESORT

2374 Caravelle Cir, KISSIMMEE

5 Beds 3 Baths 1,704 SqFt Townhouse MLS® # S5099612
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 Condominium MLS® # S5102991
FEATURED
Active 7671 Comrow St 202, KISSIMMEE

$299,950

WINDSOR HILLS, VENTURA AT WINDSOR HILLS

7671 Comrow St 202, KISSIMMEE

2 Beds 2 Baths 1,081 SqFt Condominium MLS® # S5111171
FEATURED
Active 3002 Bird Of Paradise Ln, KISSIMMEE

$279,950

ENCANTADA

3002 Bird Of Paradise Ln, KISSIMMEE

2 Beds 3 Baths 1,161 SqFt Townhouse MLS® # S5103141
FEATURED
Active 5002 Laguna Bay Cir 1, KISSIMMEE

$219,950

VILLAS AT LAGUNA BAY

5002 Laguna Bay Cir 1, KISSIMMEE

3 Beds 2 Baths 1,220 SqFt Condominium MLS® # S5114378
New FEATURED
Active 9051 Treasure Trove Ln 307, KISSIMMEE

$215,000

CARIBE COVE

9051 Treasure Trove Ln 307, KISSIMMEE

2 Beds 2 Baths 1,445 SqFt Condominium MLS® # S5115202
Active 4708 West Irlo Bronson Memorial Hwy, KISSIMMEE

$7,879,000

▼ $1,000 ACREAGE & UNREC

4708 West Irlo Bronson Memorial Hwy, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6158900
Active 4349 Boggy Creek Rd, KISSIMMEE

$6,500,000

HIGH PLAINS 2 UNREC

4349 Boggy Creek Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6241942
Active Simpson Rd, KISSIMMEE

$6,250,000

Simpson Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # S5103046
Active South Goodman Rd, KISSIMMEE

$4,800,000

FLA FRUIT & TRUCKLAND CO

South Goodman Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # R4905868
Active 3060 Gus Rd, KISSIMMEE

$4,750,000

▲ $1,250,000 ACREAGE & UNREC

3060 Gus Rd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6125360
Active 2225 East Irlon Bronson E, KISSIMMEE

$4,300,000

2225 East Irlon Bronson E, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6211605
Active 4050 Brighton Lakes Blvd, KISSIMMEE

$4,000,000

BRIGHTON LAKES PH 1

4050 Brighton Lakes Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6204727
New
Active 1026 Jack Nicklaus Ct, KISSIMMEE

$3,900,000

REUNION WEST FAIRWAYS 17 & 18 REP

1026 Jack Nicklaus Ct, KISSIMMEE

9 Beds 10 Baths 6,508 SqFt Single Family Residence MLS® # O6256407
Active Twilight Tr, KISSIMMEE

$3,800,000

▼ $1,085,000 PLEASANT HILL TRAILS UNIT 01

Twilight Tr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # L4943863
New
Active 2780 Vickie Ct, KISSIMMEE

$3,500,000

FLORIDA FRUIT BELT SALES CO 1

2780 Vickie Ct, KISSIMMEE

10 Beds 8 Baths 9,881 SqFt Single Family Residence MLS® # S5114637
Active 4013 South Orange Blossom Tr, KISSIMMEE

$3,500,000

▼ $300,000 ORANGE BLOSSOM ADD

4013 South Orange Blossom Tr, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # O6223792
Active 1020 Jack Nicklaus Ct, KISSIMMEE

$3,325,000

REUNION WEST

1020 Jack Nicklaus Ct, KISSIMMEE

8 Beds 11 Baths 6,680 SqFt Single Family Residence MLS® # O6239321
Active 43 East Lake Shore Blvd, KISSIMMEE

$3,300,000

▼ $200,000 FLORIDA FRUIT BELT SALES CO 1

43 East Lake Shore Blvd, KISSIMMEE

6 Beds 8 Baths 6,946 SqFt Single Family Residence MLS® # S5106494
Active North Poinciana Blvd, KISSIMMEE

$3,295,000

ACREAGE & UNREC

North Poinciana Blvd, KISSIMMEE

0 Beds 0 Baths 0 SqFt Land MLS® # P4931373

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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