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Kissimmee Vacation Rentals

Find 22,181 available offers from 95 partners
Kissimmee
Anytime
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Kissimmee
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Choose the perfect vacation rental

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+

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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Vacation rentals with Wi-Fi

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

House  Kissimmee
Sept 21 - Sept 28
-58%
$767
$321 per night
House ∙ 10 guests ∙ 5 bedrooms

Beautiful House in Kissimmee with Great Pool

Kissimmee, Osceola County, Florida, United States
Internet
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Cottage  Kissimmee
May 4 - May 11
-47%
$451
$239 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage in Kissimmee with Pool

Kissimmee, Osceola County, Florida, United States
Internet
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House  Kissimmee
Sept 21 - Sept 28
-67%
$955
$313 per night
House ∙ 14 guests ∙ 5 bedrooms

Vacation Home in Kissimmee with Private Pool

Kissimmee, Osceola County, Florida, United States
Internet
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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  Kissimmee
Sept 21 - Sept 28
-22%
$304
$238 per night
House ∙ 8 guests ∙ 4 bedrooms

Beautiful Vacation Home in Kissimmee with Heatable Pool + Fantastic View

4.6
Excellent (147 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
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House  Kissimmee
Sept 14 - Sept 21
-69%
$844
$264 per night
House ∙ 9 guests ∙ 4 bedrooms

House in Kissimmee with Private Pool

3.7
Good (22 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
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House  Kissimmee
Mar 8 - Mar 15
-29%
$309
$220 per night
House ∙ 11 guests ∙ 3 bedrooms

House in Kissimmee with Pool, Grill & Patio

4.4
Very good (72 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Kissimmee rental with full kitchen.

House  Kissimmee
Apr 28 - May 5
-44%
$395
$223 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Kissimmee with Wood-Burning Fireplace

4.0
Very good (11 ratings)
Kissimmee, Osceola County, Florida, United States
Kitchen
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Villa  Kissimmee
Oct 26 - Nov 2
-33%
$584
$389 per night
Villa ∙ 8 guests ∙ 4 bedrooms

Pleasant Villa in Kissimmee with Private Pool + Lake Views

4.3
Very good (39 ratings)
Kissimmee, Osceola County, Florida, United States
Kitchen
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House  Kissimmee
Apr 28 - May 5
-66%
$1,128
$387 per night
House ∙ 14 guests ∙ 5 bedrooms

Vacation Home in Kissimmee with Private Pool

4.3
Very good (70 ratings)
Kissimmee, Osceola County, Florida, United States
Kitchen
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Best Vacation Home Deals in Kissimmee

Save up to 11%

House Kissimmee
Sept 21 - Sept 28
-9%
$192
$175 per night
House ∙ 6 guests ∙ 3 bedrooms

Family Friendly Vacation Home in Kissimmee with Private Pool

3.8
Good (23 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Apr 28 - May 5
-11%
$280
$250 per night
House ∙ 8 guests ∙ 7 bedrooms

Vacation Home in Kissimmee with Free Parking

5.0
Outstanding (4 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Aug 3 - Aug 10
-8%
$198
$182 per night
Villa ∙ 10 guests ∙ 4 bedrooms

Villa in Kissimmee with Patio & Pool

4.9
Outstanding (109 ratings)
Kissimmee, Osceola County, Florida, United States
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Compare and find a dreamlike vacation rental from $142 per night by searching among the 22,181 options available in Kissimmee. HomeToGo immediately features the best offers by comparing all of the available vacation rentals in Kissimmee from its various partners.

Recommended Vacation Rentals in Kissimmee

Find your perfect vacation rental in Kissimmee: from $142 per night

Condo Kissimmee
Sept 14 - Sept 21
$235 per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo in Kissimmee with Sauna, Pool & Patio

Kissimmee, Osceola County, Florida, United States
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House Kissimmee
May 11 - May 18
$627 per night
House ∙ 16 guests ∙ 8 bedrooms

Wonderful House in Kissimmee with Patio, Yard & Pool

4.9
Outstanding (85 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Sept 21 - Sept 28
$436 per night
Villa ∙ 18 guests ∙ 1 bedroom

Villa in Kissimmee with Private Pool

Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Apr 21 - Apr 28
-65%
$492
$170 per night
House ∙ 6 guests ∙ 1 bedroom

Lovely House in Kissimmee with Pool, Yard & Grill

5.0
Outstanding (6 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Sept 21 - Sept 28
-11%
$453
$403 per night
House ∙ 12 guests ∙ 5 bedrooms

Pleasant Vacation Home in Kissimmee with Pool, Grill & Patio

5.0
Outstanding (8 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Sept 21 - Sept 28
$314 per night
Villa ∙ 10 guests ∙ 5 bedrooms

Villa in Kissimmee with Pool & Patio

4.5
Excellent (35 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Apr 28 - May 5
$226 per night
Villa ∙ 8 guests ∙ 4 bedrooms

Villa in Kissimmee with Pool

4.3
Very good (27 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
May 11 - May 18
-4%
$170
$164 per night
Villa ∙ 6 guests ∙ 3 bedrooms

Lovely Villa in Kissimmee with Patio, Pool & Jacuzzi

4.5
Excellent (76 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Sept 14 - Sept 21
-33%
$418
$281 per night
House ∙ 12 guests ∙ 6 bedrooms

Vacation Home in Kissimmee with Patio, Grill & Yard

4.6
Excellent (163 ratings)
Kissimmee, Osceola County, Florida, United States
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Budget-friendly Rentals in Kissimmee

Find Fantastic yet Inexpensive Rentals

House Kissimmee
Jun 29 - Jul 6
$337 per night
House ∙ 12 guests ∙ 6 bedrooms

Spacious Vacation Home in Kissimmee with Private Pool

4.6
Excellent (134 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Sept 21 - Sept 28
-6%
$320
$302 per night
Villa ∙ 12 guests ∙ 6 bedrooms

Villa in Kissimmee with Pool & Yard

5.0
Outstanding (5 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Sept 21 - Sept 28
-58%
$1,108
$463 per night
House ∙ 14 guests ∙ 7 bedrooms

Vacation Home in Kissimmee with Pool

4.9
Outstanding (40 ratings)
Kissimmee, Osceola County, Florida, United States
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Top-Rated Offers and Accommodations in Kissimmee

Book Vacation Rentals with the Highest User Rating

Villa Kissimmee
Aug 24 - Aug 31
$253 per night
Villa ∙ 6 guests ∙ 4 bedrooms

Gorgeous Villa in Kissimmee with Large Pool + Conservation Views

4.7
Excellent (108 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Sept 21 - Sept 28
$208 per night
House ∙ 9 guests ∙ 4 bedrooms

House in Kissimmee with Pool, Grill & Patio

4.5
Excellent (33 ratings)
Kissimmee, Osceola County, Florida, United States
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Condo Kissimmee
Sept 21 - Sept 28
-52%
$424
$202 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Kissimmee with Pool

4.6
Excellent (4 ratings)
Kissimmee, Osceola County, Florida, United States
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Popular Rental Amenities in Kissimmee

  • Pool (19,468)
  • WiFi (20,829)
  • Air conditioning (20,737)
  • Kitchen (20,651)
  • Parking (1,705)
  • Washing machine (16,524)
  • TV (19,896)
  • Dishwasher (14,258)
  • Grill (7,318)
  • Pet-friendly (1,927)
  • Microwave (15,582)
  • Balcony/patio (6,014)

Many vacationers spend more time comparing the vacation rentals offering a pool. Most of the properties have one in this destination. Apartment rental with pools in Kissimmee are a wonderful choice for groups of 8 and usually cost around $551 per night. more than half of Kissimmee's vacation rentals including a pool are located within two kilometres of water, choose between some pool time or waterfront moments.

Price and Availability Index in Kissimmee

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Vacation Rental Price Information in Kissimmee

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Kissimmee. The week with the highest average prices is in December (12/21 – 12/28). During this week, a night will cost on average $739. Conversely, the cheapest average prices are in a week of September (9/21 – 9/28).

Rental availability information in Kissimmee

Have a look at the above graph to see the global availability of vacation rentals in Kissimmee. The busiest time to book a rental in Kissimmee so far is in January (1/18 – 1/25), where only 30% rentals are available. The week with the most available rentals is in December (12/21 – 12/28), with 64% of the vacation rentals available.

The Weather in Kissimmee

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

Find the Kissimmee climate diagram. During August, maximum temperatures go up to more than 33° February is the coolest month, with average minimal temperature reaching 13°. According to the climate diagram, June is the rainiest month of the year in Kissimmee.

7-Day Weather Forecast in Kissimmee

Thu., 28 Mar.
21°
18°

10%

2 h

19 km/h

Fri., 29 Mar.
23°
21°

0%

6 h

15 km/h

Sat., 30 Mar.
26°
24°

0%

6 h

9 km/h

Sun., 31 Mar.
27°
26°

10%

4 h

6 km/h

Mon., 1 Apr.
28°
26°

0%

3 h

3 km/h

Tue., 2 Apr.
31°
30°

0%

6 h

14 km/h

Wed., 3 Apr.
31°
30°

10%

3 h

30 km/h

Accommodations for your vacation in Kissimmee

In Kissimmee, house rental are the most frequent property type. Additionally, vacation rentals in Kissimmee have an average price of $142 a night and a median size of 256 m². Moreover, these rentals are excellent if you're going in a group of 12, as that is the average number of guests house rental can welcome in Kissimmee. Users looking for something other than house rental can also compare many villa, which are the second most popular property type in Kissimmee. Villa in Kissimmee are 307 m² on average, with average prices of $745 a night.
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 22,181 rentals
💳 Possible discounts up to 18%
🌙 Nightly prices starting at $142
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 1,928 homes
🏊 Vacation rentals with pools 19,475 homes
26 reviews
Kissimmee vacation rentals have an average rating of 4/5 on 26 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Kissimmee?

We found 22,181 vacation homes in Kissimmee available for your next trip.

What are the most popular vacation home amenities in Kissimmee?

Many travellers are searching for Pool, Internet, and Air conditioning when booking a vacation home in Kissimmee.

Are there pet-friendly vacation rentals in Kissimmee?

If you're travelling with a dog, over 9% of vacation rentals in Kissimmee are pet-friendly.

What's the best month to visit Kissimmee?

The warmest time of year in Kissimmee is August and June, with the nightly price of a vacation home starting at $142.

Find the perfect Kissimmee home to match your style

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