Holiday houses & accommodation in Kissimmee - HomeToGo base64Hash Holiday houses & accommodation in Kissimmee - HomeToGo

Holiday houses & accommodation in Kissimmee

Find 28,967 available holiday rentals from 85 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended holiday rentals in Kissimmee

Rent a holiday home, apartment or cottage in Kissimmee from just $66 per night!

Villa Kissimmee
Villa ∙ 8 guests ∙ 4 bedrooms

165 m² Villa

Kissimmee, Osceola County, Florida, United States
from $257
per night
Outstanding(95 ratings)
stayz
from $257
per night
View deal
stayz
Condo Kissimmee
Condo ∙ 8 guests ∙ 3 bedrooms

Condo

Kissimmee, Osceola County, Florida, United States
from $191
per night
Excellent(12 ratings)
stayz
from $191
per night
View deal
stayz
House Kissimmee
House ∙ 6 guests ∙ 3 bedrooms

House

Kissimmee, Osceola County, Florida, United States
from $179
per night
Outstanding(1 rating)
stayz
from $179
per night
View deal
stayz
Villa Kissimmee
Villa ∙ 8 guests ∙ 4 bedrooms

Villa

Kissimmee, Osceola County, Florida, United States
from $250
per night
Outstanding(2 ratings)
stayz
from $250
per night
View deal
stayz
Villa Kissimmee
Villa ∙ 11 guests ∙ 5 bedrooms

Villa

Kissimmee, Osceola County, Florida, United States
from $224
per night
Outstanding(7 ratings)
stayz
from $224
per night
View deal
stayz
Condo Kissimmee
Condo ∙ 7 guests ∙ 3 bedrooms

Condo

Kissimmee, Osceola County, Florida, United States
from $205
per night
Excellent(23 ratings)
stayz
from $205
per night
View deal
stayz
House Kissimmee
House ∙ 6 guests ∙ 5 bedrooms

House

Kissimmee, Osceola County, Florida, United States
from $172
per night
Good(27 ratings)
stayz
from $172
per night
View deal
stayz
Villa Kissimmee
Villa ∙ 6 guests ∙ 3 bedrooms

Villa

Kissimmee, Osceola County, Florida, United States
from $186
per night
Excellent(55 ratings)
stayz
from $186
per night
View deal
stayz
House Kissimmee
House ∙ 6 guests ∙ 3 bedrooms

House

Kissimmee, Osceola County, Florida, United States
from $141
per night
(28 ratings)
stayz
from $141
per night
View deal
stayz
House Kissimmee
House ∙ 12 guests ∙ 6 bedrooms

204 m² House

Kissimmee, Osceola County, Florida, United States
from $346
per night
Excellent(6 ratings)
stayz
from $346
per night
View deal
stayz
Condo Kissimmee
Condo ∙ 8 guests ∙ 3 bedrooms

Condo

Kissimmee, Osceola County, Florida, United States
from $151
per night
Outstanding(1 rating)
stayz
from $151
per night
View deal
stayz
House Kissimmee
House ∙ 13 guests ∙ 6 bedrooms

House

Kissimmee, Osceola County, Florida, United States
from $376
per night
Outstanding(4 ratings)
stayz
from $376
per night
View deal
stayz
House Kissimmee
House ∙ 6 guests ∙ 4 bedrooms

158 m² House

Kissimmee, Osceola County, Florida, United States
from $224
per night
Outstanding(12 ratings)
stayz
from $224
per night
View deal
stayz
House Kissimmee
-51%
25 Apr - 2 May
House ∙ 10 guests ∙ 4 bedrooms

160 m² House

Kissimmee, Osceola County, Florida, United States
$859$417
per night
Excellent
Vacasa
$859$417
per night
View deal
Vacasa
House Kissimmee
24 May - 31 May
House ∙ 8 guests ∙ 4 bedrooms

164 m² House

Kissimmee, Osceola County, Florida, United States
$376
per night
Outstanding(125 ratings)
stayz
$376
per night
View deal
stayz

Vacation homes and cottages with a garden

House  Kissimmee
10 May - 17 May
-45%
$336
$186 per night
House ∙ 9 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
Free cancellation
Yard
HomeToGo
View deal
House  Kissimmee
14 Sept - 21 Sept
-42%
$840
$264 per night
House ∙ 8 guests ∙ 4 bedrooms
Kissimmee, Osceola County, Florida, United States
Free cancellation
Yard
HomeToGo
View deal
Condo  Kissimmee
2 Sept - 9 Sept
-34%
$371
$189 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
Free cancellation
Yard
HomeToGo
View deal
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Best holiday homes with a patio or terrace

House  Kissimmee
10 May - 17 May
-48%
$723
$201 per night
House ∙ 8 guests ∙ 4 bedrooms
Kissimmee, Osceola County, Florida, United States
Free cancellation
Balcony/Patio
HomeToGo
View deal
House  Kissimmee
15 Dec - 22 Dec
-38%
$684
$292 per night
House ∙ 10 guests ∙ 5 bedrooms
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
HomeToGo
View deal
House  Kissimmee
7 Dec - 14 Dec
-4%
$219
$231 per night
House ∙ 6 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
HomeToGo
View deal
See all offers

Most popular holiday houses with a fireplace

House  Kissimmee
6 Sept - 13 Sept
-48%
$873
$290 per night
House ∙ 8 guests ∙ 4 bedrooms
Kissimmee, Osceola County, Florida, United States
Free cancellation
Fireplace
HomeToGo
View deal
House  Kissimmee
30 Nov - 7 Dec
-39%
$298
$224 per night
House ∙ 10 guests ∙ 4 bedrooms
Kissimmee, Osceola County, Florida, United States
Fireplace
HomeToGo
View deal
House  Kissimmee
30 Nov - 7 Dec
-51%
$811
$305 per night
House ∙ 12 guests ∙ 4 bedrooms
Kissimmee, Osceola County, Florida, United States
Fireplace
HomeToGo
View deal
See all offers

Best holiday rental deals in Kissimmee

Save up to 56%

House Kissimmee
8 Jan - 15 Jan
-56%
$393
$211 per night
House ∙ 6 guests ∙ 3 bedrooms
4.5
Excellent
Kissimmee, Osceola County, Florida, United States
Vacasa
View deal
Resort Kissimmee
7 Jan - 14 Jan
-29%
$523
$414 per night
Resort ∙ 127 guests ∙ 1 bedroom
4.5
Excellent
Kissimmee, Osceola County, Florida, United States
Agoda
View deal
Resort Kissimmee
15 Mar - 22 Mar
-31%
$82
$66 per night
Resort ∙ 127 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
Free cancellation
Agoda
View deal

28,967 unique lettings from 85 providers can be booked in Kissimmee with prices starting at $66 a night. HomeToGo instantly compares all of these rentals so you can save up to 56%!

Budget-friendly Accommodation in Kissimmee

Find Fantastic yet Inexpensive Accommodation

House Kissimmee
from $172 per night
House ∙ 5 guests ∙ 2 bedrooms
Kissimmee, Osceola County, Florida, United States
stayz
View deal
House Kissimmee
from $240 per night
House ∙ 10 guests ∙ 4 bedrooms
4.8
Outstanding(220 ratings)
Kissimmee, Osceola County, Florida, United States
stayz
View deal
Villa Kissimmee
from $179 per night
Villa ∙ 6 guests ∙ 3 bedrooms
4.4
Very good(55 ratings)
Kissimmee, Osceola County, Florida, United States
stayz
View deal

Top-Rated Accommodation in Kissimmee

Book Holiday Offers with the Highest User Rating

Villa Kissimmee
1 Sept - 8 Sept
-46%
$946
$510 per night
Villa ∙ 12 guests ∙ 6 bedrooms
4.8
Outstanding(62 ratings)
Kissimmee, Osceola County, Florida, United States
Free cancellation
HomeToGo
View deal
Apartment Kissimmee
13 Sept - 20 Sept
-74%
$626
$171 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(26 ratings)
Kissimmee, Osceola County, Florida, United States
Free cancellation
HomeToGo
View deal
Resort Kissimmee
3 May - 10 May
-32%
$293
$214 per night
Resort ∙ 127 guests ∙ 2 bedrooms
4.6
Excellent
Kissimmee, Osceola County, Florida, United States
Free cancellation
Agoda
View deal

Customer ratings and reviews

How are reviews collected?
Jamie K.
Guest verified by HomeToGo

We loved this rental. The location is quiet and not too far from the theme parks. The house had cute Disney touches everywhere. Our family of 3 greatly appreciated the 3 bathrooms! The screened-in porch with hot tub was wonderful after a day spent walking around theme parks.

Reviewed on 28/01/2025 | Family
House Kissimmee
from $257 per night
HomeToGo
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
from $257 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Omar B.
Guest verified by HomeToGo

The area location of this townhome is safe as it is a gated community, however, on several nights there was a long line of cars waiting to enter the gates, and one night we had to wait for over 10 minutes to enter the property. The house is nicely decorated and modern, with very comfortable rooms and beds. the pool is small, more like an oversized jacuzzi, and even though the description of the property says that it is a heated pool, there is a charge of $40.00 per day to heat the pool. The kitchen was clean and well-equipped, however, we did see a few unwanted insects, I reported to the property management team and they were ready to take care of the problem. communication with the property management team was good and fast.

Reviewed on 08/12/2024 | Family
House Kissimmee
from $320 per night
HomeToGo
House ∙ 10 guests ∙ 4 bedrooms
4.0
Very good(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
from $320 per night
House ∙ 10 guests ∙ 4 bedrooms
4.0
Very good(1 rating)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Kathryn C.
Guest verified by HomeToGo

There were several issues with this home upon checking in, BUT the management company was super accommodating on getting the issues resolved quickly so we could enjoy our family vacation!

Reviewed on 02/12/2024 | Family
Villa Kissimmee
from $455 per night
HomeToGo
Villa ∙ 16 guests ∙ 8 bedrooms
4.0
Very good(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
from $455 per night
Villa ∙ 16 guests ∙ 8 bedrooms
4.0
Very good(1 rating)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Sarah M.
Guest verified by HomeToGo

Beautiful, spacious, comfortable! Beautifully decorated, clean, great location ! Large rooms, comfortable beds, awesome dining area and kitchen, great play room. Beautiful pool and pool area. We enjoyed the privacy of our rooms, we all had our own full bathrooms. We fell safe in the area. Hosts were wonderful, answered all questions promptly, really great communication! Location is excellent. I do have a suggestion, the front door and the single door to the pool need either a curtain or blinds. Also let the guests know you do not supply a change of linen unless they pay extra! That was our main complaint!

Reviewed on 01/10/2024 | Family
House Kissimmee
from $364 per night
HomeToGo
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
from $364 per night
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Vickie H.
Guest verified by HomeToGo

The house was big enough and accommodated all our Board members. But there were a few issues.

Reviewed on 08/09/2024 | Group
House Kissimmee
from $435 per night
HomeToGo
House ∙ 20 guests ∙ 10 bedrooms
4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $435 per night
House ∙ 20 guests ∙ 10 bedrooms
4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Ronnie H.
Guest verified by HomeToGo

Nice place to come back to after hours at the theme parks. better than a hotal room

Reviewed on 25/06/2024 | Family
Villa Kissimmee
from $257 per night
HomeToGo
Villa ∙ 8 guests ∙ 4 bedrooms
4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $257 per night
Villa ∙ 8 guests ∙ 4 bedrooms
4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Danielle M.
Guest verified by HomeToGo

The home was just as described (except the couch in the living room is different than the picture but no big deal!). We had enough towels and linens and everyone had plenty of space. The owners were prompt with messaging when we had questions and we got the access codes before our trip. We all felt the house was a great value!

Reviewed on 30/05/2024 | Family
House Kissimmee
from $353 per night
HomeToGo
House ∙ 12 guests ∙ 5 bedrooms
4.0
Very good(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $353 per night
House ∙ 12 guests ∙ 5 bedrooms
4.0
Very good(2 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Terry O.
Guest verified by HomeToGo

A few changes can be made. Master bath...a roach crawled up from the left sink drain. Master shower head needs to be replaced. Put a bathmat by sink on left as you enter. We could not find extra white trash bags for kitchen trash cans. We couldn't find more toilet paper or dish washing soap.

Reviewed on 14/04/2024 | Family
House Kissimmee
from $364 per night
HomeToGo
House ∙ 12 guests ∙ 5 bedrooms
4.6
Excellent(44 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $364 per night
House ∙ 12 guests ∙ 5 bedrooms
4.6
Excellent(44 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Jackie P.
Guest verified by HomeToGo

This was a great place for 3 of us ladies to get away. The price was right and the unit was just what we had hoped for. The complex was very well taken care of and the pool was beautiful (except it was not heated and too cold to swim).

Reviewed on 09/04/2024 | Group
Condo Kissimmee
from $170 per night
HomeToGo
Condo ∙ 4 guests ∙ 2 bedrooms
4.6
Excellent(63 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $170 per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.6
Excellent(63 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
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Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Kissimmee

  • Pool (23,274)
  • WiFi (26,797)
  • Air conditioning (25,412)
  • TV (23,462)
  • Washing machine (18,858)
  • Kitchen (26,258)
  • Parking (2,142)
  • Fireplace (1,616)
  • Grill (8,226)
  • Microwave (20,291)
  • Dishwasher (16,176)
  • Hot tub (7,095)

Most of the accommodation options offer a pool, which makes Kissimmee an excellent holiday destination for people looking to spend their holidays poolside. Apartment rental with pools in Kissimmee are a great choice for groups of 7 and have an average cost of $645 a night. You could also rent a rental providing a pool near the water, which is the case for one-third of the rentals on offer there.

Price and Availability Index in Kissimmee

Click on any bar to see price and availability information

Holiday Rental Price Information in Kissimmee

This graph displays average prices of the holiday cottages and holiday apartments located in Kissimmee. The most expensive dates to travel to Kissimmee are in December (20/12 – 27/12). Conversely, the cheapest average prices are in a week of August (30/08 – 06/09).

Rental availability information in Kissimmee

Have a look at the above graph to see the global availability of holiday rentals in Kissimmee. The week with the highest booking rate in the next 6 months is in November (15/11 – 22/11), where 80% of the holiday lettings are booked. People tend to travel less to Kissimmee during a week in March (29/03 – 05/04) when only 51% of the rentals are booked.

Holiday Rentals & Accommodation in Kissimmee

Information about holiday rentals in Kissimmee

🏡 Holiday rentals available 28,967 rentals
💳 Discounts available up to 56%
🌙 Nightly prices from $66
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly lettings 3,421 properties
🏊 Holiday rentals with pools 23,247 properties
1,786,292 reviews
Kissimmee holiday lettings have an average rating of 4.3/5 across 1,786,292 reviews left by travellers.

Frequently Asked Questions

How much should I expect to pay for a holiday letting in Kissimmee?

When visiting Kissimmee, you can find holiday rentals from as little as $66 per night.

How many holiday accommodation offers will I find in Kissimmee?

There are loads of options for holiday accommodation in Kissimmee, with 28,967 offers available.

What holiday rental amenities do people typically look for when visiting Kissimmee?

The top accommodation priorities for visitors to Kissimmee are Pool, Internet and Air conditioning.

How many accommodation offers are there in Kissimmee?

You can browse 28,967 holiday lettings in Kissimmee, and find great deals from $66 per night.

Are pets permitted in holiday accommodation in Kissimmee?

Yes, there are 3,421 pet-friendly holiday rentals in Kissimmee.

Top holiday destinations in Kissimmee

Top cities to visit

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