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Kissimmee Vacation Rentals

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Recommended Vacation Rentals in Kissimmee

Find your perfect vacation rental in Kissimmee: from $135 per night

Resort Kissimmee
-35%
Nov 16 - Nov 23
Resort ∙ 127 guests ∙ 3 bedrooms

Star Island Resort & Club

Kissimmee, Osceola County, Florida, United States
$248$161
per night
Very good
$248$161
per night
View deal
Resort Kissimmee
-32%
Dec 14 - Dec 21
Free cancellation
Resort ∙ 127 guests ∙ 1 bedroom

Disney's All-Star Music Resort

Kissimmee, Osceola County, Florida, United States
$488$332
per night
Excellent
$488$332
per night
View deal
Resort Kissimmee
-27%
Nov 16 - Nov 23
Free cancellation
Resort ∙ 10 guests ∙ 1 bedroom

Disney's All-Star Movies Resort

Kissimmee, Osceola County, Florida, United States
$438$318
per night
Excellent
$438$318
per night
View deal
Resort Kissimmee
-35%
Dec 14 - Dec 21
Free cancellation
Resort ∙ 127 guests ∙ 1 bedroom

Disney's All-Star Sports Resort

Kissimmee, Osceola County, Florida, United States
$478$311
per night
Excellent
$478$311
per night
View deal
House Kissimmee
Nov 9 - Nov 16
House ∙ 6 guests ∙ 4 bedrooms

House

Kissimmee, Osceola County, Florida, United States
$334
per night
$334
per night
View deal
House Kissimmee
May 10 - May 17
House ∙ 8 guests ∙ 4 bedrooms

House

Kissimmee, Osceola County, Florida, United States
$239
per night
Excellent(86 ratings)
$239
per night
View deal
House Kissimmee
-27%
May 10 - May 17
House ∙ 10 guests ∙ 5 bedrooms

195 m² House

Kissimmee, Osceola County, Florida, United States
$444$325
per night
Excellent(14 ratings)
$444$325
per night
View deal
House Kissimmee
-9%
Nov 9 - Nov 16
House ∙ 6 guests ∙ 3 bedrooms

115 m² House

Kissimmee, Osceola County, Florida, United States
$169$154
per night
Good(4 ratings)
$169$154
per night
View deal
House Kissimmee
Nov 9 - Nov 16
House ∙ 12 guests ∙ 5 bedrooms

238 m² House

Kissimmee, Osceola County, Florida, United States
$320
per night
Excellent(47 ratings)
$320
per night
View deal
Resort Kissimmee
-39%
Nov 9 - Nov 16
Resort ∙ 127 guests ∙ 2 bedrooms

FantasyWorld Resort

Kissimmee, Osceola County, Florida, United States
$330$202
per night
Excellent
$330$202
per night
View deal
House Kissimmee
Nov 9 - Nov 16
House ∙ 10 guests ∙ 4 bedrooms

House

Kissimmee, Osceola County, Florida, United States
$272
per night
$272
per night
View deal
House Kissimmee
May 10 - May 17
House ∙ 12 guests ∙ 4 bedrooms

177 m² House

Kissimmee, Osceola County, Florida, United States
$276
per night
Outstanding(2 ratings)
$276
per night
View deal
House Kissimmee
-17%
Jan 25 - Feb 1
House ∙ 10 guests ∙ 5 bedrooms

325 m² House

Kissimmee, Osceola County, Florida, United States
$413$345
per night
Outstanding(55 ratings)
$413$345
per night
View deal
Villa Kissimmee
-4%
Jan 25 - Feb 1
Villa ∙ 8 guests ∙ 4 bedrooms

184 m² Villa

Kissimmee, Osceola County, Florida, United States
$303$292
per night
Outstanding(51 ratings)
$303$292
per night
View deal
House Kissimmee
Nov 9 - Nov 16
House ∙ 6 guests ∙ 3 bedrooms

188 m² House

Kissimmee, Osceola County, Florida, United States
$212
per night
Excellent(11 ratings)
$212
per night
View deal

Vacation rentals and apartments with air conditioning

House  Kissimmee
Nov 9 - Nov 16
-5%
$379
$361 per night
House ∙ 10 guests ∙ 5 bedrooms
4.9
Outstanding(69 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
House  Kissimmee
Nov 9 - Nov 16
$326 per night
House ∙ 8 guests ∙ 4 bedrooms
4.5
Excellent(14 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
House  Kissimmee
Sept 6 - Sept 13
-61%
$1,599
$618 per night
House ∙ 20 guests ∙ 9 bedrooms
Kissimmee, Osceola County, Florida, United States
Free cancellation
Air conditioning
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Apartments with a balcony or patio

House  Kissimmee
Dec 7 - Dec 14
-4%
$197
$189 per night
House ∙ 6 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
Free cancellation
Balcony/Patio
View deal
House  Kissimmee
May 31 - Jun 7
-33%
$253
$170 per night
House ∙ 7 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
Free cancellation
Balcony/Patio
View deal
House  Kissimmee
May 22 - May 29
-38%
$351
$216 per night
House ∙ 10 guests ∙ 4 bedrooms
Kissimmee, Osceola County, Florida, United States
Free cancellation
Balcony/Patio
View deal
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Vacation homes and cottages with a garden

Villa  Kissimmee
May 10 - May 17
$272 per night
Villa ∙ 10 guests ∙ 4 bedrooms
4.7
Excellent(138 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
House  Kissimmee
Dec 7 - Dec 14
-43%
$421
$239 per night
House ∙ 8 guests ∙ 4 bedrooms
Kissimmee, Osceola County, Florida, United States
Free cancellation
Yard
View deal
House  Kissimmee
Nov 9 - Nov 16
-3%
$488
$473 per night
House ∙ 18 guests ∙ 7 bedrooms
4.8
Outstanding(94 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
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Best Vacation Home Deals in Kissimmee

Save up to 34%

Villa Kissimmee
Nov 9 - Nov 16
-7%
$358
$333 per night
Villa ∙ 11 guests ∙ 6 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
Apartment Kissimmee
Nov 30 - Dec 7
-34%
$343
$225 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
Jan 25 - Feb 1
-7%
$311
$290 per night
House ∙ 12 guests ∙ 6 bedrooms
4.3
Very good(48 ratings)
Kissimmee, Osceola County, Florida, United States
View deal

Compare and find a dreamlike vacation rental from $135 per night by searching among the 29,087 options available in Kissimmee. HomeToGo immediately features the best offers by comparing all of the available vacation rentals in Kissimmee from its various partners.

Budget-friendly Rentals in Kissimmee

Find Fantastic yet Inexpensive Rentals

Villa Kissimmee
Sept 13 - Sept 20
-39%
$406
$248 per night
Villa ∙ 8 guests ∙ 4 bedrooms
Kissimmee, Osceola County, Florida, United States
Free cancellation
View deal
House Kissimmee
Jan 25 - Feb 1
-6%
$247
$232 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding(12 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Resort Kissimmee
Jan 11 - Jan 18
$407 per night
Resort ∙ 127 guests ∙ 1 bedroom
4.5
Excellent
Kissimmee, Osceola County, Florida, United States
Free cancellation
View deal

Top-Rated Offers and Accommodations in Kissimmee

Book Vacation Rentals with the Highest User Rating

House Kissimmee
Nov 9 - Nov 16
-7%
$228
$212 per night
House ∙ 8 guests ∙ 5 bedrooms
4.8
Outstanding(8 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Villa Kissimmee
Nov 9 - Nov 16
$490 per night
Villa ∙ 12 guests ∙ 6 bedrooms
4.8
Outstanding(29 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
Nov 9 - Nov 16
$209 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(11 ratings)
Kissimmee, Osceola County, Florida, United States
View deal

Customer ratings and reviews

How are reviews collected?
Guest
Verified Guest by HomeToGo

Beautiful, spacious, comfortable! Beautifully decorated, clean, great location ! Large rooms, comfortable beds, awesome dining area and kitchen, great play room. Beautiful pool and pool area. We enjoyed the privacy of our rooms, we all had our own full bathrooms. We fell safe in the area. Hosts were wonderful, answered all questions promptly, really great communication! Location is excellent. I do have a suggestion, the front door and the single door to the pool need either a curtain or blinds. Also let the guests know you do not supply a change of linen unless they pay extra! That was our main complaint!

Reviewed on 10/1/2024 | Family
House Kissimmee
from $299 per night
HomeToGo
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
from $299 per night
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Guest
Verified Guest by HomeToGo

The house was clean and great value for the price, so much better than a hotel. My family loved the pool and the set up on the patio. Kids loved playing pool and darts in the game room. Location is great, lots of good food and was a short drive to Disney springs and Universal for us. The only thing I recommend is if you like a softer bed maybe bring a topper. We had a wonderful laid back vacation. The only bad part is we had to leave.

Reviewed on 7/21/2024 | Family
House Kissimmee
-12%
$347
from $306 per night
HomeToGo
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(85 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
-12%
$347
from $306 per night
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(85 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Guest
Verified Guest by HomeToGo

House and customer service was great throughout the whole trip! Will definitely be booking through them again! Only way to go!

Reviewed on 4/2/2024 | Group
House Kissimmee
from $181 per night
HomeToGo
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
from $181 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Guest
Verified Guest by HomeToGo

They were very attentive and quick to respond. The house was very clean. We would stay here again.

Reviewed on 3/19/2024 | Family
House Kissimmee
from $227 per night
HomeToGo
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(22 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $227 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(22 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Guest
Verified Guest by HomeToGo

It was a wonderful place for my family and I to get together while my daughter did a cheer competition. Thank you for a lovely place.

Reviewed on 5/11/2023 | Family
House Kissimmee
from $321 per night
HomeToGo
House ∙ 14 guests ∙ 6 bedrooms
4.3
Very good(86 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $321 per night
House ∙ 14 guests ∙ 6 bedrooms
4.3
Very good(86 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Guest
Verified Guest by HomeToGo

We enjoy this place! The distance from Walt Disney is good, the resort is nice. One night we did’t have a parking place in front of our house but the rest of the time it was ok. The swimming pool behind our house was great after a day walking in the sun.

Reviewed on 4/21/2023 | Family
House Kissimmee
from $244 per night
HomeToGo
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(11 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $244 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(11 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Guest
Verified Guest by HomeToGo

This place was absolutely fantastic. We had 4 adults and 2 kids. Could have easily fit another 6 people with us.

Reviewed on 1/15/2023 | Family
House Kissimmee
from $394 per night
HomeToGo
House ∙ 12 guests ∙ 5 bedrooms
4.8
Outstanding(54 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $394 per night
House ∙ 12 guests ∙ 5 bedrooms
4.8
Outstanding(54 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
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Why choose HomeToGo?

Securely pay and stay your way

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Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Kissimmee

  • Pool (22,983)
  • WiFi (26,885)
  • Air conditioning (25,453)
  • Kitchen (26,141)
  • Parking (2,220)
  • Washing machine (18,725)
  • TV (23,630)
  • Dishwasher (16,318)
  • Grill (8,428)
  • Pet-friendly (3,397)
  • Microwave (20,458)
  • Balcony/patio (5,847)

Many vacationers spend more time comparing the vacation rentals offering a pool. More than two-thirds 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 $597 per night. one-third 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 $825. Conversely, the cheapest average prices are in a week of August (8/30 – 9/6).

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 September (9/27 – 10/4), where only 19% rentals are available. The week with the most available rentals is in December (12/14 – 12/21), with 49% 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 29,195 rentals
🌙 Nightly prices starting at $132
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 3,406 homes
🏊 Vacation rentals with pools 23,104 homes
53 reviews
Kissimmee vacation rentals have an average rating of 4/5 on 53 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Kissimmee?

We found 29,195 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 12% 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 $132.

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