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Kissimmee Vacation Rentals

Find 21,801 available offers from 100 partners
Kissimmee
Anytime
Guests
Kissimmee
Anytime
Guests

Popular Filters to find the Perfect Rental in Kissimmee

2 Adults
1 Bedroom
4 Adults
Pets allowed
Pool
House
Internet

Vacation rentals with Wi-Fi

House  Kissimmee
Apr 5 - Apr 12
$355 per night
House ∙ 8 guests ∙ 3 bedrooms

House with Private Pool

5.0
Outstanding (4 ratings)
Kissimmee, Osceola County, Florida, United States
Internet
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Resort  Kissimmee
Aug 21 - Aug 28
-25%
$198
$148 per night
Resort ∙ 127 guests ∙ 3 bedrooms

Big Resort with Hot Tub, Pool & Sauna

4.2
Very good
Kissimmee, Osceola County, Florida, United States
Free cancellation
Internet
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House  Kissimmee
Oct 12 - Oct 19
$430 per night
House ∙ 16 guests ∙ 5 bedrooms

Vacation Home for Memorable Getaway with Private Pool, Terrace & Yard | Lake View | Perfect for Remote Work

4.5
Excellent (26 ratings)
Kissimmee, Osceola County, Florida, United States
Internet
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Vacation rentals and apartments with air conditioning

Resort  Kissimmee
Aug 17 - Aug 24
-32%
$290
$198 per night
Resort ∙ 127 guests ∙ 2 bedrooms

Resort with Jacuzzi, BBQ & Pool | Good for Workation

4.6
Excellent
Kissimmee, Osceola County, Florida, United States
Free cancellation
Air conditioning
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House  Kissimmee
Apr 5 - Apr 12
-7%
$350
$326 per night
House ∙ 10 guests ∙ 4 bedrooms

House with Private Pool, Barbecue & Garden | Nature View

4.8
Outstanding (210 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
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House  Kissimmee
Apr 5 - Apr 12
-7%
$221
$205 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home with Heated Pool & Barbeque | Lake View

4.8
Outstanding (8 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
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Apartments and vacation rentals with a kitchen

House  Kissimmee
Aug 1 - Aug 8
-3%
$365
$353 per night
House ∙ 10 guests ∙ 5 bedrooms

Children-Friendly Lovely Vacation Home with Private Pool, Terrace & Grill | Good for Workation | Pet-Friendly

4.6
Excellent (19 ratings)
Kissimmee, Osceola County, Florida, United States
Kitchen
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Villa  Kissimmee
Apr 5 - Apr 12
-7%
$213
$198 per night
Villa ∙ 8 guests ∙ 3 bedrooms

Fully Equipped Nice Villa with Pool, Sauna & Barbeque | Pets Are Welcome

4.9
Outstanding (106 ratings)
Kissimmee, Osceola County, Florida, United States
Kitchen
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House  Kissimmee
Oct 13 - Oct 20
-55%
$585
$263 per night
House ∙ 8 guests ∙ 4 bedrooms

House with Private Pool, Barbeque & Patio | Lake View

4.0
Very good (10 ratings)
Kissimmee, Osceola County, Florida, United States
Kitchen
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Best Vacation Home Deals in Kissimmee

Save up to 81%

Resort Kissimmee
Jul 23 - Jul 30
-45%
$420
$232 per night
Resort ∙ 10 guests ∙ 1 bedroom

Family-Friendly Wonderful Resort with Pool

4.5
Excellent
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Apr 5 - Apr 12
-3%
$287
$278 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home with Private Pool & BBQ | Lake View

5.0
Outstanding (4 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Sept 10 - Sept 17
-81%
$3,423
$663 per night
House ∙ 33 guests ∙ 15 bedrooms

Child-Friendly Vacation Home for Family Getaway with Garden, Private Pool & Hot Tub | Water View | Good for Workation

Kissimmee, Osceola County, Florida, United States
Free cancellation
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Compare and find a dreamlike vacation rental from $135 per night by searching among the 21,801 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 $135 per night

House Kissimmee
Aug 1 - Aug 8
$334 per night
House ∙ 12 guests ∙ 5 bedrooms

Child-Friendly Beautiful Vacation Home with Private Pool, Yard & Patio | Nature View

4.8
Outstanding (270 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Apr 5 - Apr 12
$553 per night
House ∙ 15 guests ∙ 6 bedrooms

Family-Oriented Spacious House with Barbecue, Patio & Private Pool

4.7
Excellent (68 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Apr 5 - Apr 12
$204 per night
Villa ∙ 8 guests ∙ 3 bedrooms

Family-Oriented Pleasant Villa with Heated Pool

4.5
Excellent (11 ratings)
Kissimmee, Osceola County, Florida, United States
Free cancellation
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House Kissimmee
May 11 - May 18
-8%
$539
$499 per night
House ∙ 12 guests ∙ 5 bedrooms

House with Barbeque, Private Pool & Patio

4.6
Excellent (37 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
May 11 - May 18
$309 per night
House ∙ 10 guests ∙ 5 bedrooms

Child-Friendly Lovely Vacation Home with Patio, Private Pool & BBQ

4.6
Excellent (93 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Aug 1 - Aug 8
-7%
$302
$280 per night
House ∙ 9 guests ∙ 4 bedrooms

Children-Friendly Ample Vacation Home with Barbeque, Private Pool & Yard | Lake View

4.8
Outstanding (138 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Aug 24 - Aug 31
$254 per night
Villa ∙ 6 guests ∙ 4 bedrooms

Children-Friendly Wonderful Villa with Terrace, Yard & Private Pool | Nature View

4.7
Excellent (108 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Apr 5 - Apr 12
$338 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home with Garden, BBQ & Patio

5.0
Outstanding (122 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Apr 5 - Apr 12
$622 per night
House ∙ 14 guests ∙ 6 bedrooms

Children-Friendly House with Private Pool, Terrace & Sauna | Nature View

5.0
Outstanding (184 ratings)
Kissimmee, Osceola County, Florida, United States
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Budget-friendly Rentals in Kissimmee

Find Fantastic yet Inexpensive Rentals

Villa Kissimmee
Apr 5 - Apr 12
-9%
$225
$204 per night
Villa ∙ 10 guests ∙ 4 bedrooms

Child-Friendly Villa with Heated Pool & Terrace

4.7
Excellent (76 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Oct 13 - Oct 20
-4%
$274
$264 per night
House ∙ 9 guests ∙ 3 bedrooms

Children-Friendly Wonderful House with Barbecue, Heated Pool & Sauna | Pets Are Welcome

4.8
Outstanding (8 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Aug 24 - Aug 31
$298 per night
House ∙ 9 guests ∙ 4 bedrooms

Vacation Home with Private Pool & BBQ

4.7
Excellent (44 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
Apr 5 - Apr 12
-7%
$412
$385 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home with Garden, Private Pool & Jacuzzi

4.8
Outstanding (142 ratings)
Kissimmee, Osceola County, Florida, United States
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Villa Kissimmee
Apr 5 - Apr 12
$313 per night
Villa ∙ 10 guests ∙ 5 bedrooms

Children-Friendly Lovely Villa with Private Pool & Terrace

4.7
Excellent (38 ratings)
Kissimmee, Osceola County, Florida, United States
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House Kissimmee
Apr 5 - Apr 12
-7%
$391
$362 per night
House ∙ 8 guests ∙ 4 bedrooms

Children-Friendly Vacation Home with Yard, Terrace & Barbeque

4.8
Outstanding (10 ratings)
Kissimmee, Osceola County, Florida, United States
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Popular Rental Amenities in Kissimmee

  • Pool (19,322)
  • WiFi (20,626)
  • Air conditioning (20,407)
  • Kitchen (20,393)
  • Parking (1,747)
  • Washing machine (16,199)
  • TV (19,415)
  • Dishwasher (14,159)
  • Grill (7,698)
  • Pet-friendly (1,860)
  • Microwave (15,485)
  • Balcony/patio (5,927)

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 $559 per night. nearly 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 $732. Conversely, the cheapest average prices are in a week of August (8/31 – 9/7).

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 25% rentals are available. The week with the most available rentals is in October (10/5 – 10/12), with 50% of the vacation rentals available.

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.

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

Information about vacation rentals in Kissimmee

🏡 Vacation rentals available 21,801 rentals
💳 Possible discounts up to 37%
🌙 Nightly prices starting at $135
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 1,888 homes
🏊 Vacation rentals with pools 19,231 homes
47 reviews
Kissimmee vacation rentals have an average rating of 3.8/5 on 47 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Kissimmee?

We found 21,801 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 $135.

Find the perfect Kissimmee home to match your style

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