Vacation homes in Kissimmee - Casamundo base64Hash Vacation homes in Kissimmee - Casamundo

Vacation homes in Kissimmee

Anytime
Guests
Anytime
Guests
2,290 accommodations available

  • Price per night

    • Up to €100
    • €100 - €199
    • From €200

  • Accommodation types

    • House
    • Apartment
    • Other

  • Distance to center

    • 1 mi
    • 2 mi
    • 3 mi

  • Rating

    • 4.5+
    • 4+

  • Popular amenities

    • Pool
    • WiFi
    • Air conditioning
    • Kitchen
    • Parking
    • Washing machine
    • TV
    • Dishwasher
    • Microwave
    • Balcony/patio
    • Hot tub
    • Garden
    • Cot
    • Fireplace
    • Sauna

  • Other Services

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Kissimmee

Discover your ideal Kissimmee vacation rental with real-time comparisons of 2,290 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below – check the full description before booking.
Villa Kissimmee
438 m² villa ∙ 30 guests ∙ 10 bedrooms

Villa with hot tub, private pool & garden

Kissimmee, Osceola County, Florida, United States
This stunning villa in Kissimmee accommodates up to 30 guests and features a private pool, hot tub, and a fully equipped kitchen, perfect for a memorable getaway! Enjoy a...
from €256
per night
Excellent(22 ratings)
from €256
per night
Check prices
House Kissimmee
448 m² house ∙ 26 guests ∙ 12 bedrooms

House with hot tub, garden & private pool | City view

Kissimmee, Osceola County, Florida, United States
This spacious Kissimmee house rental accommodates 26 guests and features a private pool, hot tub, a full kitchen, and a family-friendly yard—perfect for a memorable getaw...
from €280
per night
from €280
per night
Check prices
House Kissimmee
151 m² house ∙ 6 guests ∙ 3 bedrooms

Child-friendly holiday home with private pool & hot tub | City view

Kissimmee, Osceola County, Florida, United States
This stunning house rental in Kissimmee offers breathtaking lake and sea views, a private heated pool, hot tub, and a fully equipped kitchen, perfect for family fun and r...
from €114
per night
from €114
per night
Check prices
House Kissimmee
303 m² house ∙ 27 guests ∙ 12 bedrooms

Family-oriented holiday home with private pool, hot tub & garden | City view | Pets allowed

Kissimmee, Osceola County, Florida, United States
This spacious house rental in Kissimmee accommodates up to 27 guests, featuring a private pool, hot tub, family-friendly amenities, a yard, and pet-friendly options—perfe...
from €291
per night
from €291
per night
Check prices
House Kissimmee
151 m² house ∙ 8 guests ∙ 4 bedrooms

Family-friendly house with private pool, garden & hot tub | City view

Kissimmee, Osceola County, Florida, United States
This spacious house rental in Kissimmee welcomes up to 8 guests and features a private pool, spa, hot tub, kitchen, and balcony. A perfect family-friendly retreat awaits ...
from €116
per night
from €116
per night
Check prices
House Kissimmee
264 m² house ∙ 14 guests ∙ 7 bedrooms

Fully equipped charming house with garden, sauna & pool

Kissimmee, Osceola County, Florida, United States
This stunning waterfront house rental in Kissimmee accommodates up to 14 guests and features a refreshing pool, relaxing hot tub, fully equipped kitchen, spacious yard, a...
from €214
per night
from €214
per night
Check prices
House Kissimmee
399 m² house ∙ 16 guests ∙ 9 bedrooms

Family-friendly holiday home with private pool

Kissimmee, Osceola County, Florida, United States
This spacious house rental in Kissimmee accommodates up to 16 guests and features a private pool, a full kitchen, and ample parking, making it perfect for family gatherin...
from €254
per night
from €254
per night
Check prices
House Kissimmee
303 m² house ∙ 16 guests ∙ 8 bedrooms

Holiday home with hot tub, garden & private pool | City view

Kissimmee, Osceola County, Florida, United States
This spacious house rental in Kissimmee comfortably accommodates up to 16 guests, featuring a private pool, hot tub, family-friendly amenities, and a large yard for outdo...
from €209
per night
Good(3 ratings)
from €209
per night
Check prices
Condo Kissimmee
113 m² condo ∙ 8 guests ∙ 3 bedrooms

Family-friendly big flat with pool | Suitable for remote work

Kissimmee, Osceola County, Florida, United States
This spacious condo in Kissimmee accommodates up to 8 guests and features a pool, spa, kitchen, and balcony. Perfect for families and events, plus convenient parking!
from €100
per night
from €100
per night
Check prices
House Kissimmee
192 m² house ∙ 8 guests ∙ 4 bedrooms

Child-friendly lovely house with private pool

Kissimmee, Osceola County, Florida, United States
This spacious house rental in Kissimmee accommodates up to 8 guests, featuring a private heated pool, a full kitchen, and ample parking, perfect for family gatherings and...
from €162
per night
Outstanding(11 ratings)
from €162
per night
Check prices
House Kissimmee
267 m² house ∙ 10 guests ∙ 5 bedrooms

House with barbeque & private pool

Kissimmee, Osceola County, Florida, United States
This spacious house rental in Kissimmee welcomes up to 10 guests and features a heated private pool, a fully equipped kitchen, and ample parking, perfect for family gathe...
from €249
per night
from €249
per night
Check prices
House Kissimmee
182 m² house ∙ 10 guests ∙ 4 bedrooms

Holiday home with jacuzzi & private pool | Lake view

Kissimmee, Osceola County, Florida, United States
This stunning house rental in Kissimmee offers a heated private pool, a hot tub, and beautiful lake views, making it perfect for family gatherings or events. Enjoy spacio...
from €154
per night
Excellent(29 ratings)
from €154
per night
Check prices
House Kissimmee
326 m² house ∙ 12 guests ∙ 6 bedrooms

House with private pool & barbeque | Lake view

Kissimmee, Osceola County, Florida, United States
This stunning house rental in Kissimmee accommodates 12 guests and features a private heated pool, spa, and beautiful lake and sea views, perfect for family gatherings an...
from €274
per night
Outstanding(4 ratings)
from €274
per night
Check prices
House Kissimmee
622 m² house ∙ 10 guests ∙ 5 bedrooms

Family-oriented holiday home with garden, jacuzzi & private pool | City view

Kissimmee, Osceola County, Florida, United States
This stunning Kissimmee house rental offers a private pool, hot tub, and beautiful lake views, perfect for family gatherings of up to 10. Enjoy the waterfront yard and sp...
from €191
per night
from €191
per night
Check prices
House Kissimmee
266 m² house ∙ 12 guests ∙ 6 bedrooms

Children-friendly house with private pool, garden & barbecue | City view | Pets are welcome

Kissimmee, Osceola County, Florida, United States
Experience the ultimate family getaway in this spacious Kissimmee house rental, featuring a private pool, fully equipped kitchen, balcony, and yard—perfect for up to 12 g...
from €145
per night
from €145
per night
Check prices

Vacation Homes with Pools

Make a splash: Check out these Kissimmee vacation rentals refreshing pools!

We use AI to generate the short summary in each offer below – check the full description before booking.
Villa Kissimmee
from €298 per night
371 m² Villa ∙ 21 guests ∙ 9 bedrooms

Villa with private pool, garden & jacuzzi

5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
Pool
Check prices
Condo Kissimmee
from €102 per night
123 m² Condo ∙ 8 guests ∙ 3 bedrooms

Flat with pool

Kissimmee, Osceola County, Florida, United States
Pool
Check prices
House Kissimmee
from €272 per night
308 m² House ∙ 14 guests ∙ 7 bedrooms

Family-friendly beautiful holiday home with private pool & hot tub | Lake view

4.1
Very good(10 ratings)
Kissimmee, Osceola County, Florida, United States
Pool
Check prices
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Vacation rentals and apartments with air conditioning

Cool comfort in Kissimmee: Choose a vacation rental with air conditioning - book your stay!

We use AI to generate the short summary in each offer below – check the full description before booking.
House Kissimmee
from €91 per night
119 m² House ∙ 6 guests ∙ 3 bedrooms

House with pool, barbeque & garden | City view

Kissimmee, Osceola County, Florida, United States
Air conditioning
Check prices
House Kissimmee
from €248 per night
395 m² House ∙ 22 guests ∙ 10 bedrooms

Holiday home with private pool, garden & barbecue | Water view | Perfect for remote work

Kissimmee, Osceola County, Florida, United States
Air conditioning
Check prices
House Kissimmee
from €194 per night
375 m² House ∙ 20 guests ∙ 8 bedrooms

Child-friendly holiday home with BBQ, private pool & garden | City view

Kissimmee, Osceola County, Florida, United States
Air conditioning
Check prices
See all offers
585 reviews
585 travelers who stayed in Kissimmee gave their vacation rental an average rating of 4.2/5 stars.

Frequently asked questions

What are the most popular accommodations in the area?

The most in-demand accommodations in Kissimmee are house rentals and villa. With 2,290 offers in Kissimmee, we always find the perfect accommodation for you.

How much does it cost to stay the night?

With Casamundo you can find rentals in Kissimmee starting at €91 - On average, you will stay in a 326 m² (Villa) or a 284 m² (House rentals).

Do you offer pet-friendly house rentals in Kissimmee?

We have the perfect options for you and your furry companions. Apartment rental are the most pet-friendly accommodations in Kissimmee with an average price of €396 per night.

Do you offer accommodations for traveling with a group?

We can help you find accommodations in Kissimmee for a group. On average, the house rentals has space for 13 guests.

Find the perfect accommodation to stay in Kissimmee

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