Book Holiday Homes in Kissimmee

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Featured Holiday Homes in Kissimmee

The Berkley, Orlando

The Berkley, Orlando

4 out of 5
8545 W. Irlo Bronson Highway, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 15 May to 16 May
AU$225
includes taxes & fees
15 May - 16 May
With a stay at The Berkley, Orlando in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center.
The Berkley, Orlando
Maple Leaf Inn & Suites

Maple Leaf Inn & Suites

2.5 out of 5
Kissimmee
With a stay at Maple Leaf Inn & Suites in Kissimmee, you'll be within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets.
Maple Leaf Inn & Suites
Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes

4 out of 5
Formosa Vly Pl, Kissimmee, FL
With a stay at Formosa Valley Resort by UNE Homes in Kissimmee, you'll be a 3-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® ...
Formosa Valley Resort by UNE Homes
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Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney

Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney

Kissimmee
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town.
Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney
Encore Resort

Encore Resort

4 out of 5
101 Lasso Drive, Kissimmee, FL
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Disney's Hollywood Studios®.
Encore Resort
Beautiful and cozy home at Sonoma Resort

Beautiful and cozy home at Sonoma Resort

Kissimmee
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets.
Beautiful and cozy home at Sonoma Resort
Tropical villa overlooking the lake with a private pool, spa, grill, & AC

Tropical villa overlooking the lake with a private pool, spa, grill, & AC

Kissimmee
With a stay at this vacation home in Kissimmee (Cumbrian Lakes), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets.
Tropical villa overlooking the lake with a private pool, spa, grill, & AC
Single Story, Private Pool, Water Views, Game Room | Sleeps 11

Single Story, Private Pool, Water Views, Game Room | Sleeps 11

Kissimmee
With a stay at this vacation home in Kissimmee (Cumbrian Lakes), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets.
Single Story, Private Pool, Water Views, Game Room | Sleeps 11
Upstay - 27 Guest Home w Private Pool & Hot Tub

Upstay - 27 Guest Home w Private Pool & Hot Tub

Kissimmee
With a stay at this vacation home, you'll be centrally located in Kissimmee, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets.
Upstay - 27 Guest Home w Private Pool & Hot Tub
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Kissimmee Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Kissimmee vacation homes are the perfect way for you to wing it.

Holiday houses in Kissimmee let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Kissimmee in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Kissimmee adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Kissimmee with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Kissimmee vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Kissimmee Holiday Homes essential information

Accommodation
16211 Holiday Homes
Lowest Price
AU$123
Highest Price
AU$225
Popular accommodation
The Berkley, Orlando, Maple Leaf Inn & Suites, Formosa Valley Resort by UNE Homes, Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney, Encore Resort, Beautiful and cozy home at Sonoma Resort, Tropical villa overlooking the lake with a private pool, spa, grill, & AC, Single Story, Private Pool, Water Views, Game Room | Sleeps 11, Upstay - 27 Guest Home w Private Pool & Hot Tub

Top trending hotels in Kissimmee

Vacation Village at Parkway

Vacation Village at Parkway

3 out of 5
2975 Arabian Nights Blvd, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is AU$161 per night from 27 Apr to 28 Apr
AU$161
includes taxes & fees
27 Apr - 28 Apr
Located in Kissimmee, Vacation Village at Parkway is in the entertainment district, within a 5-minute drive of Old Town and Fun Spot America.
Vacation Village at Parkway
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

3 out of 5
7470 W. Irlo Bronson Memorial Hwy., Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is AU$123 per night from 27 Apr to 28 Apr
AU$123
includes taxes & fees
27 Apr - 28 Apr
Located in Kissimmee, Ramada by Wyndham Kissimmee Gateway is on the Strip, within a 10-minute drive of ESPN Wide World of Sports Complex and Disney's Hollywood ...
Ramada by Wyndham Kissimmee Gateway
Holiday Inn & Suites Orlando SW - Celebration Area by IHG

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

3 out of 5
5711 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundable
The price is AU$162 per night from 27 Apr to 28 Apr
AU$162
includes taxes & fees
27 Apr - 28 Apr
With a stay at Holiday Inn & Suites Orlando SW - Celebration Area by IHG, you'll be centrally located in Kissimmee, within a 10-minute walk of Old Town and Fun ...
Holiday Inn & Suites Orlando SW - Celebration Area by IHG
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Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
4944 W. Irlo Bronson Memorial Highway, Kissimmee, FL
The price is AU$143 per night from 20 Apr to 21 Apr
AU$143
includes taxes & fees
20 Apr - 21 Apr
With a stay at Palazzo Lakeside Hotel in Kissimmee, you'll be a 4-minute drive from Old Town and 9 minutes from Disney Springs™.
Palazzo Lakeside Hotel
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.