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Kissimmee Vacation Rentals

Find 21,679 available offers from 92 partners
Kissimmee
Anytime
Guests
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
Oct 21 - Oct 28
-29%
$1,010
$719 per night
House ∙ 25 guests ∙ 12 bedrooms

House in Kissimmee with Pool, Grill & Yard

Kissimmee, Osceola County, Florida, United States
Free cancellation
Internet
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House  Kissimmee
May 18 - May 25
-15%
$269
$228 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Kissimmee with Wood-Burning Fireplace

4.0
Very good (9 ratings)
Kissimmee, Osceola County, Florida, United States
Internet
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Villa  Kissimmee
May 11 - May 18
-27%
$330
$240 per night
Villa ∙ 12 guests ∙ 4 bedrooms

Villa in Kissimmee with Grill, Pool & Yard

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
Aug 24 - Aug 31
-42%
$298
$172 per night
House ∙ 6 guests ∙ 1 bedroom

Lovely House in Kissimmee with Jacuzzi, Pool & Yard

5.0
Outstanding (5 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
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House  Kissimmee
Nov 1 - Nov 8
-34%
$291
$193 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Kissimmee with Grill, Patio & Pool

Kissimmee, Osceola County, Florida, United States
Air conditioning
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Villa  Kissimmee
May 11 - May 18
$206 per night
Villa ∙ 8 guests ∙ 4 bedrooms

Charming Villa in Kissimmee with Free Pool

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.

Villa  Kissimmee
May 9 - May 16
$294 per night
Villa ∙ 8 guests ∙ 4 bedrooms

Pleasant Villa in Kissimmee with Private Pool + Lake Views

4.4
Very good (34 ratings)
Kissimmee, Osceola County, Florida, United States
Kitchen
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House  Kissimmee
May 25 - Jun 1
-4%
$403
$388 per night
House ∙ 12 guests ∙ 5 bedrooms

House in Kissimmee with Private Pool

4.4
Very good (42 ratings)
Kissimmee, Osceola County, Florida, United States
Kitchen
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Villa  Kissimmee
Aug 24 - Aug 31
-7%
$211
$196 per night
Villa ∙ 8 guests ∙ 3 bedrooms

Beautiful Villa in Kissimmee with Pool, Sauna & Grill

4.9
Outstanding (102 ratings)
Kissimmee, Osceola County, Florida, United States
Kitchen
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Best Vacation Home Deals in Kissimmee

Save up to 23%

House Kissimmee
May 11 - May 18
-11%
$279
$248 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Kissimmee with Patio & Yard

5.0
Outstanding (3 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
May 11 - May 18
-7%
$193
$180 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Kissimmee with Pool, Patio & Grill

4.6
Excellent (110 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
May 25 - Jun 1
-23%
$540
$416 per night
House ∙ 10 guests ∙ 5 bedrooms

House in Kissimmee with South-Facing Pool

4.7
Excellent (6 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 21,679 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

House Kissimmee
May 25 - Jun 1
$227 per night
House ∙ 8 guests ∙ 4 bedrooms

Private Vacation Home in Kissimmee with Private Pool + Conservation View

4.4
Very good (92 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Mar 9 - Mar 16
$258 per night
House ∙ 6 guests ∙ 3 bedrooms

Beautiful Vacation Home in Kissimmee with Private Pool

Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Aug 10 - Aug 17
$239 per night
House ∙ 11 guests ∙ 5 bedrooms

Child Friendly Vacation Home in Kissimmee with Private Garden

4.7
Excellent (17 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
May 11 - May 18
$245 per night
Villa ∙ 6 guests ∙ 3 bedrooms

Beautiful Villa in Kissimmee with Double Garage + Lake View

4.4
Very good (87 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
May 11 - May 18
$245 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Kissimmee with Pool

4.9
Outstanding (27 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Feb 23 - Mar 2
$219 per night
House ∙ 11 guests ∙ 3 bedrooms

House in Kissimmee with Pool, Grill & Patio

4.4
Very good (69 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Nov 23 - Nov 30
-3%
$219
$212 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Kissimmee with Private Pool

4.5
Excellent (94 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Aug 24 - Aug 31
$438 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Kissimmee with Private Pool + Lake View

4.5
Excellent (41 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Aug 24 - Aug 31
-12%
$227
$201 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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Budget-friendly Rentals in Kissimmee

Find Fantastic yet Inexpensive Rentals

Villa Kissimmee
May 18 - May 25
-7%
$334
$310 per night
Villa ∙ 12 guests ∙ 6 bedrooms

Villa in Kissimmee with Pool & Yard

5.0
Outstanding (4 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
May 9 - May 16
-39%
$532
$323 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Kissimmee with Resort-Style Pool

4.3
Very good (27 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Aug 10 - Aug 17
$179 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Kissimmee with Pool, Sauna & Patio

4.7
Excellent (25 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

House Kissimmee
Feb 15 - Feb 22
$233 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Kissimmee with Private Pool

4.6
Excellent (197 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Feb 15 - Feb 22
-3%
$233
$226 per night
House ∙ 5 guests ∙ 3 bedrooms

Beautiful Vacation Home in Kissimmee with Private Pool

4.6
Excellent (42 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Apr 27 - May 4
$201 per night
Villa ∙ 8 guests ∙ 3 bedrooms

Private Villa in Kissimmee with Pool

4.5
Excellent (11 ratings)
Kissimmee, Osceola County, Florida, United States
Free cancellation
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Popular Rental Amenities in Kissimmee

  • Pool (19,770)
  • WiFi (21,108)
  • Air conditioning (20,974)
  • Kitchen (20,964)
  • Parking (1,744)
  • Washing machine (16,618)
  • TV (20,136)
  • Dishwasher (14,473)
  • Grill (7,395)
  • Pet-friendly (1,937)
  • Microwave (15,787)
  • Balcony/patio (6,052)

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 $553 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

Click on any bar to see price and availability information

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 $747. Conversely, the cheapest average prices are in a week of September (9/14 – 9/21).

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 November (11/30 – 12/7), where only 30% rentals are available. The week with the most available rentals is in May (5/18 – 5/25), with 68% of the vacation rentals available.

The Weather in Kissimmee

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24°
14°
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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.
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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.
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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

Sun., 25 Feb.
21°
19°

0%

6 h

10 km/h

Mon., 26 Feb.
22°
20°

0%

6 h

10 km/h

Tue., 27 Feb.
25°
22°

10%

4 h

13 km/h

Wed., 28 Feb.
27°
23°

10%

3 h

18 km/h

Thu., 29 Feb.
25°
21°

10%

2 h

20 km/h

Fri., 1 Mar.
22°
21°

0%

1 h

29 km/h

Sat., 2 Mar.
21°
21°

15%

0 h

25 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 259 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 $725 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 21,679 rentals
💳 Possible discounts up to 12%
🌙 Nightly prices starting at $142
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 1,849 homes
🏊 Vacation rentals with pools 18,955 homes
37 reviews
Kissimmee vacation rentals have an average rating of 3.9/5 on 37 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Kissimmee?

We found 21,679 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.

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