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

Holiday houses & accommodation in Kissimmee

Find 23,010 available offers from 105 partners
Kissimmee
Anytime
Guests
Kissimmee
Anytime
Guests

Popular Filters to find the Perfect Letting in Kissimmee

Pets allowed
1 Bedroom
2 Adults
House
4 Adults
Farmhouse
200 m to water

Vacation rentals with Wi-Fi

If it's for remote work or watching your favourite programmes, fast WiFi can be a must-have feature when it comes to selecting a holiday letting. Take a look at HomeToGo's range of holiday homes with internet in Kissimmee and be sure of a quick and reliable connection during your visit.

House  Kissimmee
7 Sept - 14 Sept
-52%
$471
$225 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Kissimmee with Pool

Kissimmee, Osceola County, Florida, United States
Free cancellation
Internet
Details
HomeToGo
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House  Kissimmee
26 Oct - 2 Nov
-55%
$535
$243 per night
House ∙ 6 guests ∙ 3 bedrooms

Beautiful Holiday Home in Kissimmee

4.5
Excellent
Kissimmee, Osceola County, Florida, United States
Internet
Details
Vacasa
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House  Kissimmee
21 May - 28 May
-60%
$591
$235 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Kissimmee with Pool

5.0
Outstanding
Kissimmee, Osceola County, Florida, United States
Internet
Details
Vacasa
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Vacation rentals and apartments with air conditioning

Good weather while travelling is always brilliant - and it's an added bonus to be able to control the temperature in your holiday letting too. Find holiday rentals in Kissimmee with air conditioning to make your visit even more comfortable.

House  Kissimmee
15 June - 22 June
-71%
$1,052
$305 per night
House ∙ 8 guests ∙ 4 bedrooms

Nice House in Kissimmee with Private Pool

4.0
Very good
Kissimmee, Osceola County, Florida, United States
Air conditioning
Details
Vacasa
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House  Kissimmee
6 Nov - 13 Nov
-71%
$1,679
$494 per night
House ∙ 20 guests ∙ 8 bedrooms

Pleasant Holiday Home in Kissimmee with Huge Pool

3.9
Good (36 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
Details
Vacasa
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House  Kissimmee
16 Oct - 23 Oct
-57%
$880
$377 per night
House ∙ 12 guests ∙ 5 bedrooms

House in Kissimmee with Pool & Barbecue

4.0
Very good
Kissimmee, Osceola County, Florida, United States
Air conditioning
Details
Vacasa
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Apartments and vacation rentals with a kitchen

Searching for self-catering holiday homes in Kissimmee? Find the ideal rental for you with our range of Kissimmee holiday lettings with kitchens. Well furnished with all the needed appliances, these accommodation offers are perfect for self-catered stays.

House  Kissimmee
19 May - 26 May
-55%
$1,355
$617 per night
House ∙ 17 guests ∙ 7 bedrooms

Beautiful Holiday Home in Kissimmee with Screened-In Patio

4.1
Very good (40 ratings)
Kissimmee, Osceola County, Florida, United States
Kitchen
Details
Vacasa
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House  Kissimmee
9 Nov - 16 Nov
-58%
$771
$322 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Kissimmee with Pool, Hot Tub & Terrace

3.6
Good (16 ratings)
Kissimmee, Osceola County, Florida, United States
Kitchen
Details
Vacasa
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House  Kissimmee
19 May - 26 May
-57%
$670
$286 per night
House ∙ 10 guests ∙ 5 bedrooms

House in Kissimmee with Pool

5.0
Outstanding
Kissimmee, Osceola County, Florida, United States
Kitchen
Details
Vacasa
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Best holiday rental deals in Kissimmee

Save up to 69%

House Kissimmee
19 May - 26 May
-52%
$585
$279 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Kissimmee with Pool & Terrace

5.0
Outstanding (7 ratings)
Kissimmee, Osceola County, Florida, United States
Details
Vacasa
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House Kissimmee
12 Oct - 19 Oct
-40%
$603
$362 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Kissimmee with Outdoor Pool

4.0
Very good
Kissimmee, Osceola County, Florida, United States
Details
Vacasa
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House Kissimmee
30 May - 6 June
-69%
$1,070
$332 per night
House ∙ 11 guests ∙ 5 bedrooms

Holiday Home in Kissimmee with Pool

4.5
Excellent
Kissimmee, Osceola County, Florida, United States
Details
Vacasa
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23,010 unique lettings from 105 providers can be booked in Kissimmee with prices starting at $140 a night. HomeToGo instantly compares all of these rentals so you can save up to 65%!

Recommended holiday rentals in Kissimmee

Rent a holiday home, apartment or cottage in Kissimmee from just $140 per night

House Kissimmee
11 Sept - 18 Sept
-58%
$1,551
$645 per night
House ∙ 25 guests ∙ 9 bedrooms

House in Orlando with Pool & Garden

Kissimmee, Osceola County, Florida, United States
Free cancellation
Details
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House Kissimmee
21 May - 28 May
$338 per night
House ∙ 12 guests ∙ 6 bedrooms

House in Acadia Estates with Private Pool

4.5
Excellent
Kissimmee, Osceola County, Florida, United States
Details
Vacasa
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Resort Kissimmee
26 May - 2 June
-22%
$296
$231 per night
Resort ∙ 127 guests ∙ 1 bedroom

Resort in Lake Buena Vista with Outdoor Pool

3.8
Good
Kissimmee, Osceola County, Florida, United States
Free cancellation
Details
Agoda
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Resort Kissimmee
26 May - 2 June
-81%
$716
$133 per night
Resort ∙ 127 guests ∙ 1 bedroom

Resort in Florida Center with Outdoor Pool

4.6
Excellent
Kissimmee, Osceola County, Florida, United States
Details
Agoda
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House Kissimmee
$319 per night
House ∙ 14 guests ∙ 7 bedrooms

Holiday Home in Kissimmee with Pool

4.9
Outstanding (41 ratings)
Kissimmee, Osceola County, Florida, United States
Details
stayz
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House Kissimmee
$270 per night
House ∙ 14 guests ∙ 5 bedrooms

Holiday Home in Kissimmee with Private Pool

4.3
Very good (70 ratings)
Kissimmee, Osceola County, Florida, United States
Details
stayz
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House Kissimmee
$234 per night
House ∙ 6 guests ∙ 3 bedrooms

Holiday Home in Kissimmee with Wood-Burning Fireplace

4.3
Very good (14 ratings)
Kissimmee, Osceola County, Florida, United States
Details
stayz
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House Kissimmee
$247 per night
House ∙ 12 guests ∙ 5 bedrooms

Family Friendly House in Kissimmee with Private Pool + Lake View

3.3
(15 ratings)
Kissimmee, Osceola County, Florida, United States
Details
stayz
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House Kissimmee
$363 per night
House ∙ 10 guests ∙ 5 bedrooms

Holiday Home in Kissimmee with Terrace & Pool

5.0
Outstanding (2 ratings)
Kissimmee, Osceola County, Florida, United States
Details
stayz
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Budget-friendly Accommodation in Kissimmee

Find Fantastic yet Inexpensive Accommodation

House Kissimmee
$408 per night
House ∙ 14 guests ∙ 6 bedrooms

Holiday Home in Kissimmee with Screened-In Pool

3.8
Good (65 ratings)
Kissimmee, Osceola County, Florida, United States
Details
stayz
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House Kissimmee
$212 per night
House ∙ 8 guests ∙ 4 bedrooms

Beautiful Holiday Home in Kissimmee with Heatable Pool + Fantastic View

4.6
Excellent (144 ratings)
Kissimmee, Osceola County, Florida, United States
Details
stayz
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House Kissimmee
$195 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Kissimmee with Private Pool

4.6
Excellent (33 ratings)
Kissimmee, Osceola County, Florida, United States
Details
stayz
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Top-Rated Accommodation in Kissimmee

Book Holiday Offers with the Highest User Rating

House Kissimmee
$275 per night
House ∙ 12 guests ∙ 6 bedrooms

Holiday Home in Kissimmee with Pool, Barbecue & Terrace

4.8
Outstanding (258 ratings)
Kissimmee, Osceola County, Florida, United States
Details
stayz
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House Kissimmee
12 Oct - 19 Oct
-65%
$1,073
$373 per night
House ∙ 14 guests ∙ 6 bedrooms

House in Kissimmee with Outdoor Pool

4.5
Excellent
Kissimmee, Osceola County, Florida, United States
Details
Vacasa
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House Kissimmee
5 Oct - 12 Oct
-61%
$1,586
$617 per night
House ∙ 18 guests ∙ 7 bedrooms

Holiday Home in Kissimmee with Hot Tub, Pool & Sauna

5.0
Outstanding
Kissimmee, Osceola County, Florida, United States
Details
Vacasa
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Popular holiday rental amenities in Kissimmee

  • Pool (20,075)
  • WiFi (21,466)
  • Air conditioning (21,489)
  • TV (20,646)
  • Washing machine (17,235)
  • Kitchen (21,422)
  • Parking (1,876)
  • Fireplace (1,625)
  • Grill (7,761)
  • Microwave (16,418)
  • Dishwasher (15,062)
  • Hot tub (3,270)

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 8 and have an average cost of $608 a night. You could also rent a rental providing a pool near the water, which is the case for more than half 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 (21/12 – 28/12). Conversely, the cheapest average prices are in a week of August (31/08 – 07/09).

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 January (25/01 – 01/02), where 77% of the holiday lettings are booked. People tend to travel less to Kissimmee during a week in November (30/11 – 07/12) when only 44% of the rentals are booked.

The weather in Kissimmee

max.
Min.
24°
14°
2 days 2
max.
Min.
23°
13°
4 days 4
max.
Min.
26°
15°
4 days 4
max.
Min.
29°
19°
5 days 5
max.
Min.
30°
21°
6 days 6
max.
Min.
32°
23°
14 days 14
max.
Min.
32°
24°
14 days 14
max.
Min.
33°
24°
14 days 14
max.
Min.
31°
23°
10 days 10
max.
Min.
29°
20°
4 days 4
max.
Min.
25°
16°
4 days 4
max.
Min.
24°
15°
3 days 3
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

You can see our climate diagram above. August is the warmest month of the year in Kissimmee with temperatures reaching a maximum average of 33°. No heat wave is expected in February, where minimum average temperatures usally hit a 13° low. The month of January has nice weather with only 2 rainy days.

7-Day Weather Forecast in Kissimmee

Sat, 18 May
36°
33°

5%

4 h

19 km/h

Sun, 19 May
29°
23°

55%

0 h

12 km/h

Mon, 20 May
34°
30°

10%

6 h

20 km/h

Tue, 21 May
33°
29°

10%

3 h

17 km/h

Wed, 22 May
35°
31°

5%

4 h

16 km/h

Thu, 23 May
35°
35°

0%

6 h

9 km/h

Fri, 24 May
36°
33°

5%

4 h

17 km/h

Holiday Rentals & Accommodation in Kissimmee

Information about holiday rentals in Kissimmee

🏡 Holiday rentals available 23,010 rentals
💳 Discounts available up to 65%
🌙 Nightly prices from $140
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly lettings 2,197 properties
🏊 Holiday rentals with pools 20,089 properties
61 reviews
Kissimmee holiday lettings have an average rating of 3.9/5 across 61 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 $140 per night.

How many holiday accommodation offers will I find in Kissimmee?

There are loads of options for holiday accommodation in Kissimmee, with 23,010 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 23,010 holiday lettings in Kissimmee, and find great deals from $140 per night.

Are pets permitted in holiday accommodation in Kissimmee?

Yes, there are 2,197 pet-friendly holiday rentals in Kissimmee.

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