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Kissimmee Vacation Rentals

Find 19,428 available offers from 88 partners
Kissimmee
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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Resort
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
3.5+

Discover Magical Theme Parks From Your Kissimmee Vacation Rental

Many Kissimmee vacation rentals are modern, spacious apartments and homes within a short drive of the area's major theme parks.

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Best Vacation Home Deals in Kissimmee

Save up to 44%

House Kissimmee
Aug 26 - Sept 2
-44%
$561
$314 per night
House ∙ 8 guests ∙ 4 bedrooms
Charming Vacation Home in Kissimmee with Private Pool + Lake View
4.8
"Excellent" (10 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Nov 18 - Nov 25
-26%
$317
$235 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Kissimmee with Private Pool
4.9
"Excellent" (134 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Aug 11 - Aug 18
-38%
$483
$299 per night
House ∙ 14 guests ∙ 5 bedrooms
Vacation Home in Kissimmee with Screened-In Patio
4.7
"Outstanding" (7 ratings)
Kissimmee, Osceola County, Florida, United States
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19,428 beautiful properties from 86 partner websites can be booked in Kissimmee, with prices beginning at $140 per night. By comparing these accommodations, HomeToGo features the most economical offers as well as the highest rated vacation homes in Kissimmee.

Top-Rated Offers and Accommodations in Kissimmee

Book Vacation Rentals with the Highest User Rating

Villa Kissimmee
Nov 3 - Nov 10
$226 per night
Villa ∙ 6 guests ∙ 3 bedrooms
Villa in Four Corners with Private Pool
5.0
"Excellent" (163 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Sept 2 - Sept 9
-17%
$390
$323 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Four Corners with Free Pool
4.8
"Excellent" (135 ratings)
Kissimmee, Osceola County, Florida, United States
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Condo Kissimmee
Aug 19 - Aug 26
$185 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Condo in Four Corners with Hot Tub, Sauna & Pool
4.7
"Outstanding" (71 ratings)
Kissimmee, Osceola County, Florida, United States
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Recommended Vacation Rentals in Kissimmee

Find your perfect vacation rental in Kissimmee: from $137 per night

House Kissimmee
Mar 2 - Mar 9
$239 per night
House ∙ 9 guests ∙ 4 bedrooms
Pleasant Vacation Home in Kissimmee with Private Pool
4.7
"Outstanding" (115 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Oct 21 - Oct 28
-65%
$1,759
$621 per night
House ∙ 14 guests ∙ 6 bedrooms
House in Kissimmee with Grill & Pool
5.0
"Excellent" (14 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Aug 23 - Aug 30
-43%
$985
$565 per night
House ∙ 12 guests ∙ 6 bedrooms
Vacation Home in Kissimmee with Front Pool
5.0
"Excellent" (5 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Jan 9 - Jan 16
-39%
$355
$215 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Kissimmee with Pool
4.7
"Outstanding" (31 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Apr 14 - Apr 21
$296 per night
House ∙ 6 guests ∙ 5 bedrooms
House in Kissimmee with Private Pool
4.9
"Excellent" (125 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Sept 30 - Oct 7
$279 per night
Villa ∙ 8 guests ∙ 4 bedrooms
Villa in Kissimmee with Private Pool
4.9
"Excellent" (134 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Sept 2 - Sept 9
$315 per night
House ∙ 8 guests ∙ 4 bedrooms
Wonderful House in Kissimmee with Private Pool
4.9
"Excellent" (120 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Jan 9 - Jan 16
$276 per night
Villa ∙ 7 guests ∙ 3 bedrooms
Villa in Kissimmee with Pool & Grill + Lake Views
4.7
"Outstanding" (102 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Jan 9 - Jan 16
$271 per night
Villa ∙ 6 guests ∙ 3 bedrooms
Villa in Davenport with Electric Garage
4.9
"Excellent" (119 ratings)
Kissimmee, Osceola County, Florida, United States
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Budget-friendly Rentals in Kissimmee

Find Fantastic yet Inexpensive Rentals

House Kissimmee
Sept 30 - Oct 7
-31%
$357
$248 per night
House ∙ 8 guests ∙ 5 bedrooms
House in Four Corners with Outdoor Pool
5.0
"Excellent" (192 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Nov 4 - Nov 11
$342 per night
Villa ∙ 13 guests ∙ 6 bedrooms
Villa in Four Corners with Large Pool + Waterside Views
4.7
"Outstanding" (113 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Sept 2 - Sept 9
$312 per night
House ∙ 9 guests ∙ 4 bedrooms
Vacation Home in Four Corners with Private Pool + Majestic Views
4.9
"Excellent" (112 ratings)
Kissimmee, Osceola County, Florida, United States
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Kissimmee accommodation with high-speed internet.

House Internet Kissimmee
Dec 2 - Dec 9
-18%
$367
$303 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Kissimmee with Private Pool
4.5
"Outstanding" (4 ratings)
Kissimmee, Osceola County, Florida, United States
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House Internet Kissimmee
Nov 11 - Nov 18
$252 per night
House ∙ 7 guests ∙ 3 bedrooms
Vacation Home in Kissimmee with Private Pool
4.8
"Excellent" (88 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Internet Kissimmee
Jan 6 - Jan 13
$256 per night
Villa ∙ 10 guests ∙ 4 bedrooms
Villa in Kissimmee with Large Pool + Lake View
4.8
"Excellent" (124 ratings)
Kissimmee, Osceola County, Florida, United States
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Kissimmee and book a vacation rental with air conditioning.

House Air conditioning Kissimmee
Apr 14 - Apr 21
$368 per night
House ∙ 12 guests ∙ 5 bedrooms
Wonderful Vacation Home in Kissimmee with Pool, Yard & Grill
4.9
"Excellent" (236 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Air conditioning Kissimmee
Aug 26 - Sept 2
$477 per night
Villa ∙ 14 guests ∙ 6 bedrooms
Villa in Kissimmee with Outdoor Pool + Superb Views
4.9
"Excellent" (78 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Air conditioning Kissimmee
Jun 29 - Jul 6
$424 per night
Villa ∙ 8 guests ∙ 4 bedrooms
Villa in Kissimmee with Pool & Yard + Lake View
5.0
"Excellent" (31 ratings)
Kissimmee, Osceola County, Florida, United States
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Vacation homes and cottages with a garden

Looking for vacation homes with a little extra outdoor space? Check out these accommodations in Kissimmee with private yards.

House Yard Kissimmee
Aug 5 - Aug 12
$236 per night
House ∙ 5 guests ∙ 3 bedrooms
Family Friendly House in Kissimmee with Private Pool
4.8
"Excellent" (116 ratings)
Kissimmee, Osceola County, Florida, United States
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House Yard Kissimmee
Sept 30 - Oct 7
-17%
$377
$314 per night
House ∙ 10 guests ∙ 4 bedrooms
Spacious Vacation Home in Kissimmee with Private Pool
5.0
"Excellent" (9 ratings)
Kissimmee, Osceola County, Florida, United States
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House Yard Kissimmee
Nov 4 - Nov 11
$240 per night
House ∙ 5 guests ∙ 3 bedrooms
House in Kissimmee with Private Pool
5.0
"Excellent" (84 ratings)
Kissimmee, Osceola County, Florida, United States
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Popular Rental Amenities in Kissimmee

  • Pool (17,993)
  • WiFi (19,335)
  • Air conditioning (18,912)
  • Kitchen (18,636)
  • Parking (1,650)
  • Washing machine (15,712)
  • TV (18,291)
  • Dishwasher (15,081)
  • Grill (7,382)
  • Pet-friendly (1,495)
  • Microwave (17,380)
  • Balcony/patio (2,212)

Many vacationers spend more time comparing the vacation rentals with a pool. Most of the accommodations have one. Also, accommodations with pools in Kissimmee cost, on average, $621 per night. Most of the available rentals with pools are condo. In Kissimmee, many of the rentals offering a pool are situated close to the water.

Price and Availability Index in Kissimmee

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Vacation Rental Price Information in Kissimmee

We rendered price information data on the above graph to give you more insights on prices in Kissimmee. in Kissimmee, prices can go up to $733 (12/23 - 12/30). On the other hand, in September you will find the cheapest prices (9/14 - 9/21). Prices this week are on average $359 a night.

Rental availability information in Kissimmee

The graph shows the weekly availability rate in Kissimmeefor the next twelve months. The week with the highest booking rate in the next 12 months is in May (5/11 - 5/18), where 73% of the vacation rentals are booked. June (6/15 - 6/22) has got the highest percentage of available rentals.

The Weather in Kissimmee

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

Find the Kissimmee climate diagram. On average, the warmest month is August. February is the coolest month, with average minimal temperature reaching 13°. The wettest month is June with 14 rainy days on average. On the contrary, there is an average of only 2 rainy days in January, which is the driest month.

7-Day Weather Forecast in Kissimmee

Sun., 24 Sep.
31°
20°

10%

9 h

9 km/h

Mon., 25 Sep.
32°
22°

10%

10 h

13 km/h

Tue., 26 Sep.
30°
24°

15%

5 h

15 km/h

Wed., 27 Sep.
30°
23°

15%

4 h

12 km/h

Thu., 28 Sep.
30°
24°

15%

5 h

16 km/h

Fri., 29 Sep.
29°
24°

15%

2 h

19 km/h

Sat., 30 Sep.
29°
24°

15%

4 h

22 km/h

What are the best activities for families in Kissimmee?

Discovery Cove and SeaWorld

For a break from theme parks' fast pace and crowds, take the kids to Discovery Cove for the day. Swim with dolphins, interact with stingrays, walk along the reef with a dive helmet, and snorkel on the coral reef before relaxing on the lazy river and beaches.

Older children will love the big coasters at SeaWorld, such as Manta and Kraken. The whole family will enjoy the dolphin and whale shows, massive aquarium, and touch pools.

Where are the unique attractions in Kissimmee?

Disney World and Universal Studios

Disney World, the theme park that made Orlando famous, comprises four distinct parks: Disney World, Hollywood Studios, Animal Kingdom, Magic Kingdom, and Epcot. You'll need to spend at least a day in each park to get the most out of a Disney vacation. Magic Kingdom, the most popular of the parks, is home to the famous Disney castle at the end of Main Street.

Universal Studios is great for those with older children. Visit the Wizarding World of Harry Potter, spend a day swimming and rocketing down high-speed water slides at Volcano Bay, and experience all the classic Universal attractions, such as E.T Adventure, the Simpsons Ride, and the Incredible Hulk Coaster

What are the best events and festivals in Kissimmee?

The Epcot International Food & Wine Festival

Book your Kissimmee condo rentals far in advance for the Epcot International Food & Wine Festival. Walk your way around the world and taste different wines and foods from various countries at little popup stalls around the lagoon at this popular fall event.

You could also time your visit to see the Disney World Marathon, held over a weekend every January. Events include a full marathon, fun kids' runs, and a health expo.

Information about vacation rentals in Kissimmee

🏡 Vacation rentals available 19,428 homes
💳 Possible discounts up to 44%
🌙 Nightly prices starting at $140
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 1,417 homes
🏊 Vacation rentals with pools 17,360 homes

Frequently Asked Questions

What is the typical price of a vacation home in Kissimmee?

The nightly price for accommodation in Kissimmee starts at $140.

What is the typical availability of House rental in Kissimmee?

We found 19,428 vacation homes in Kissimmee available for your next trip.

What are the most popular vacation home amenities in Kissimmee?

The most popular amenities for rentals in Kissimmee include vacation homes with Pool, Internet, or Air conditioning.

How many House rental and Villa can I find in Kissimmee?

Kissimmee has 19,428 House rental and Villa available to book.

Are there pet-friendly vacation rentals in Kissimmee?

Finding a vacation rental in Kissimmee that allows dogs is definitely possible, with 1,417 pet-friendly homes on offfer.

What's the best month to visit Kissimmee?

When booking accommodation in Kissimmee, remember that the rainiest months are usually June and July, with January often being the sunniest.

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