Kissimmee Vacation Rentals - Wimdu base64Hash Kissimmee Vacation Rentals - Wimdu

Kissimmee Vacation Rentals

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Choose from 28,881 vacation rentals and homes for your trip!

Best-rated vacation rentals in Kissimmee

Discover vacation rentals with top-notch guest ratings

House Kissimmee
from $146 per night
House ∙ 12 guests ∙ 5 bedrooms

244 m² House

4.6
Excellent(9 ratings)
Kissimmee, Osceola County, Florida, United States
Vacasa
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Villa Kissimmee
from $680 per night
Villa ∙ 48 guests ∙ 22 bedrooms

929 m² Villa

5.0
Outstanding(4 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
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House Kissimmee
from $388 per night
House ∙ 24 guests ∙ 10 bedrooms

427 m² House

5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
HomeToGo
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Pet-friendly rentals in Kissimmee

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

House Kissimmee
from $317 per night
House ∙ 24 guests ∙ 9 bedrooms

399 m² House

5.0
Outstanding(2 ratings)
Kissimmee, Osceola County, Florida, United States
Pet-friendly
HomeToGo
View deal
House Kissimmee
from $174 per night
House ∙ 12 guests ∙ 5 bedrooms

244 m² House

4.6
Excellent(9 ratings)
Kissimmee, Osceola County, Florida, United States
Pet-friendly
Vrbo
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Resort Kissimmee
from $94 per night
Resort ∙ 127 guests ∙ 4 bedrooms

Regal Oaks Resort by IDILIQ

4.2
Very good
Kissimmee, Osceola County, Florida, United States
Pet-friendly
Agoda
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Vacation rentals with pool in Kissimmee

Discover best cabin and house rentals with pool in Kissimmee

House Kissimmee
from $272 per night
24 guests ∙ 12 bedrooms

House

Kissimmee, Osceola County, Florida, United States
Pool
HomeToGo
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House Kissimmee
from $385 per night
26 guests ∙ 13 bedrooms

House

Kissimmee, Osceola County, Florida, United States
Pool
HomeToGo
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Resort Kissimmee
from $129 per night
Resort ∙ 4 guests ∙ 1 bedroom

Disney's All-Star Movies Resort

4.4
Very good
Kissimmee, Osceola County, Florida, United States
Pool
Agoda
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See all offers with pool

Best vacation rental offers in Kissimmee

House Kissimmee
from $130 per night
House ∙ 10 guests ∙ 4 bedrooms

157 m² House

3.5
Good
Kissimmee, Osceola County, Florida, United States
Vacasa
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House Kissimmee
from $136 per night
House ∙ 8 guests ∙ 3 bedrooms

120 m² House

3.5
Good
Kissimmee, Osceola County, Florida, United States
Vacasa
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House Kissimmee
from $112 per night
House ∙ 6 guests ∙ 3 bedrooms

120 m² House

Kissimmee, Osceola County, Florida, United States
Vacasa
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Villa Kissimmee
from $316 per night
Villa ∙ 24 guests ∙ 9 bedrooms

399 m² Villa

Kissimmee, Osceola County, Florida, United States
HomeToGo
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House Kissimmee
from $394 per night
30 guests ∙ 12 bedrooms

House

Kissimmee, Osceola County, Florida, United States
HomeToGo
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House Kissimmee
from $418 per night
House ∙ 30 guests ∙ 12 bedrooms

453 m² House

Kissimmee, Osceola County, Florida, United States
HomeToGo
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House Kissimmee
from $195 per night
House ∙ 12 guests ∙ 6 bedrooms

201 m² House

4.3
Very good(31 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
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House Kissimmee
from $319 per night
House ∙ 12 guests ∙ 6 bedrooms

306 m² House

5.0
Outstanding
Kissimmee, Osceola County, Florida, United States
Vacasa
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House Kissimmee
from $310 per night
15 guests ∙ 7 bedrooms

House

4.7
Excellent(20 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
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House Kissimmee
from $284 per night
House ∙ 20 guests ∙ 8 bedrooms

302 m² House

4.4
Very good(6 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
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House Kissimmee
from $220 per night
House ∙ 15 guests ∙ 6 bedrooms

267 m² House

Kissimmee, Osceola County, Florida, United States
Vrbo
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House Kissimmee
from $179 per night
House ∙ 15 guests ∙ 7 bedrooms

279 m² House

4.6
Excellent(68 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
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House Kissimmee
from $164 per night
House ∙ 9 guests ∙ 5 bedrooms

232 m² House

4.7
Excellent(146 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
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House Kissimmee
from $376 per night
House ∙ 25 guests ∙ 9 bedrooms

399 m² House

4.8
Outstanding(4 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
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House Kissimmee
from $192 per night
House ∙ 15 guests ∙ 7 bedrooms

245 m² House

3.8
Good(5 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
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Villa Kissimmee
from $171 per night
11 guests ∙ 5 bedrooms

Villa

4.8
Outstanding(8 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
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House Kissimmee
from $125 per night
House ∙ 8 guests ∙ 4 bedrooms

172 m² House

3.8
Good(10 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
View deal
House Kissimmee
from $182 per night
House ∙ 12 guests ∙ 6 bedrooms

5000 m² House

3.2
(19 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
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House Kissimmee
from $123 per night
House ∙ 10 guests ∙ 4 bedrooms

177 m² House

3.6
Good(93 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
View deal
House Kissimmee
from $216 per night
House ∙ 14 guests ∙ 6 bedrooms

204 m² House

4.9
Outstanding(42 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
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House Kissimmee
from $201 per night
House ∙ 10 guests ∙ 4 bedrooms

189 m² House

Kissimmee, Osceola County, Florida, United States
Vrbo
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House Kissimmee
from $209 per night
8 guests ∙ 4 bedrooms

House

Kissimmee, Osceola County, Florida, United States
Vrbo
View deal
Villa Kissimmee
from $129 per night
Villa ∙ 10 guests ∙ 4 bedrooms

167 m² Villa

4.0
Very good(60 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
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House Kissimmee
from $309 per night
House ∙ 27 guests ∙ 10 bedrooms

397 m² House

Kissimmee, Osceola County, Florida, United States
HomeToGo
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House Kissimmee
from $295 per night
12 guests ∙ 7 bedrooms

House

5.0
Outstanding(2 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
View deal
House Kissimmee
from $110 per night
House ∙ 8 guests ∙ 3 bedrooms

117 m² House

5.0
Outstanding
Kissimmee, Osceola County, Florida, United States
Vacasa
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House Kissimmee
from $134 per night
House ∙ 10 guests ∙ 4 bedrooms

149 m² House

4.5
Excellent(4 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
View deal
House Kissimmee
from $136 per night
12 guests ∙ 6 bedrooms

House

4.6
Excellent(128 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
View deal
House Kissimmee
from $104 per night
House ∙ 8 guests ∙ 4 bedrooms

132 m² House

4.0
Very good(54 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
View deal
House Kissimmee
from $171 per night
House ∙ 8 guests ∙ 4 bedrooms

240 m² House

3.4
(18 ratings)
Kissimmee, Osceola County, Florida, United States
Vrbo
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Show all 26423 apartments in Kissimmee

Price and Availability Index in Kissimmee

Click on any bar to see price and availability information

Vacation Rental Price Information in Kissimmee

We analyzed the prices of accommodation in Kissimmee to help you find the best time to travel. The average accommodation price reaches its highest point in december (12/27 – 1/3), at $455 per night. The average accommodation price reaches its minimum in september (9/20 – 9/27), at $364 per night.

Rental availability information in Kissimmee

This graph shows the availability of vacation rentals at different times of year. The most popular time of year to visit Kissimmee is April. The week with the highest availability is in September (9/13 – 9/20) - 52% of the vacation rentals are still available.

Apartments & Vacation rentals Kissimmee

The leisure paradise in sunny Florida: vacation apartments in Kissimmee

In Kissimmee you will find numerous spacious vacation homes, many of which are equipped with their own pool. But the offer also includes comfortable vacation homes, from which you can reach the restaurants and attractions of the city in a few minutes.

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1,782,789 reviews
1,782,789 travelers who stayed in Kissimmee rated their vacation home 4.3/5 stars on average.

And we love our apartments

157 m² House
120 m² House
120 m² House
399 m² Villa
House
Show all 26423 apartments in Kissimmee

Features of Kissimmee vacation rentals

💳 Discounts up to 26%
⭐ Popular amenities Air conditioning, Pool and Internet
🏊  Vacation rentals with a pool 22,914 rentals
🌙 Minimum price starting at $62
🐾 Pet friendly vacation homes 3,260 rentals
🏡 Rentals available 28,881 rentals

Other Popular Vacation Destinations

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