Kissimmee Vacation Rentals - HomeToGo base64Hash Kissimmee Vacation Rentals - HomeToGo

Kissimmee Vacation Rentals

Find 28,841 available home rentals from 82 partners
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Top 15 Recommended vacation rentals in Kissimmee

Find your perfect vacation rental in Kissimmee from just $96 per night!

House Kissimmee
House ∙ 12 guests ∙ 6 bedrooms

201 m² House

Kissimmee, Osceola County, Florida, United States
from $247
per night
Very good(32 ratings)
from $247
per night
View deal
House Kissimmee
House ∙ 14 guests ∙ 6 bedrooms

204 m² House

Kissimmee, Osceola County, Florida, United States
from $273
per night
Outstanding(44 ratings)
from $273
per night
View deal
House Kissimmee
House ∙ 16 guests ∙ 9 bedrooms

House

Kissimmee, Osceola County, Florida, United States
from $386
per night
from $386
per night
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House Kissimmee
House ∙ 14 guests ∙ 7 bedrooms

House

Kissimmee, Osceola County, Florida, United States
from $322
per night
Very good(34 ratings)
from $322
per night
View deal
House Kissimmee
House ∙ 15 guests ∙ 7 bedrooms

279 m² House

Kissimmee, Osceola County, Florida, United States
from $264
per night
Excellent(67 ratings)
from $264
per night
View deal
House Kissimmee
House ∙ 15 guests ∙ 7 bedrooms

House

Kissimmee, Osceola County, Florida, United States
from $429
per night
Excellent(20 ratings)
from $429
per night
View deal
House Kissimmee
House ∙ 10 guests ∙ 4 bedrooms

177 m² House

Kissimmee, Osceola County, Florida, United States
from $202
per night
Good(93 ratings)
from $202
per night
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House Kissimmee
House ∙ 14 guests ∙ 6 bedrooms

267 m² House

Kissimmee, Osceola County, Florida, United States
from $242
per night
Outstanding(4 ratings)
from $242
per night
View deal
House Kissimmee
House ∙ 14 guests ∙ 7 bedrooms

235 m² House

Kissimmee, Osceola County, Florida, United States
from $276
per night
Very good(60 ratings)
from $276
per night
View deal
House Kissimmee
House ∙ 12 guests ∙ 6 bedrooms

5000 m² House

Kissimmee, Osceola County, Florida, United States
from $245
per night
(19 ratings)
from $245
per night
View deal
House Kissimmee
House ∙ 9 guests ∙ 5 bedrooms

232 m² House

Kissimmee, Osceola County, Florida, United States
from $273
per night
Excellent(149 ratings)
from $273
per night
View deal
House Kissimmee
House ∙ 18 guests ∙ 7 bedrooms

308 m² House

Kissimmee, Osceola County, Florida, United States
from $374
per night
Outstanding(4 ratings)
from $374
per night
View deal
House Kissimmee
House ∙ 18 guests ∙ 9 bedrooms

409 m² House

Kissimmee, Osceola County, Florida, United States
from $443
per night
Excellent(70 ratings)
from $443
per night
View deal
House Kissimmee
House ∙ 12 guests ∙ 5 bedrooms

278 m² House

Kissimmee, Osceola County, Florida, United States
from $279
per night
Outstanding(4 ratings)
from $279
per night
View deal
House Kissimmee
House ∙ 20 guests ∙ 8 bedrooms

302 m² House

Kissimmee, Osceola County, Florida, United States
from $392
per night
Excellent(7 ratings)
from $392
per night
View deal

Vacation rentals and apartments with air conditioning

House  Kissimmee
from $144 per night
House ∙ 10 guests ∙ 5 bedrooms

166 m² House

3.7
Good(144 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
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House  Kissimmee
from $231 per night
10 guests ∙ 4 bedrooms

House

4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
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House  Kissimmee
from $303 per night
House ∙ 8 guests ∙ 4 bedrooms

240 m² House

3.4
(18 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
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Apartments with a balcony or patio

Villa  Kissimmee
from $311 per night
Villa ∙ 13 guests ∙ 6 bedrooms

303 m² Villa

4.6
Excellent(144 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
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Villa  Kissimmee
from $177 per night
Villa ∙ 10 guests ∙ 4 bedrooms

167 m² Villa

4.0
Very good(61 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
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House  Kissimmee
from $173 per night
House ∙ 8 guests ∙ 4 bedrooms

149 m² House

4.8
Outstanding(10 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
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Vacation homes and cottages with a garden

House  Kissimmee
from $413 per night
24 guests ∙ 12 bedrooms

House

Kissimmee, Osceola County, Florida, United States
Yard
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House  Kissimmee
from $191 per night
House ∙ 10 guests ∙ 4 bedrooms

177 m² House

5.0
Outstanding(3 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
House  Kissimmee
from $206 per night
House ∙ 13 guests ∙ 4 bedrooms

186 m² House

4.1
Very good(26 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
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Budget-friendly Rentals in Kissimmee

Find Fantastic yet Inexpensive Rentals

House Kissimmee
from $220 per night
8 guests ∙ 3 bedrooms

House

5.0
Outstanding(4 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
from $186 per night
12 guests ∙ 6 bedrooms

House

4.5
Excellent(129 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
from $186 per night
House ∙ 10 guests ∙ 5 bedrooms

169 m² House

4.1
Very good(19 ratings)
Kissimmee, Osceola County, Florida, United States
View deal

Top-Rated Offers and Accommodations in Kissimmee

Book Vacation Rentals with the Highest User Rating

House Kissimmee
from $309 per night
House ∙ 12 guests ∙ 6 bedrooms

288 m² House

5.0
Outstanding(199 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Villa Kissimmee
from $653 per night
Villa ∙ 18 guests ∙ 9 bedrooms

375 m² Villa

4.8
Outstanding(165 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
from $360 per night
House ∙ 18 guests ∙ 8 bedrooms

567 m² House

4.9
Outstanding(43 ratings)
Kissimmee, Osceola County, Florida, United States
View deal

Customer ratings and reviews

How are reviews collected?
LaQuinna F.
Guest verified by HomeToGo

We all enjoyed staying in this beautiful home. The kids thought it was amazing and didn’t want to leave. Most of the time we were in the pool and the theater. Everything we need in the area was very close we could have walked. For it to been so busy with most of the homes filled, it was still quiet. Will definitely be returning.

Reviewed on 4/26/2025 | Family
House Kissimmee
from $555 per night
HomeToGo
House ∙ 24 guests ∙ 9 bedrooms
5.0
Outstanding(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Tami Jo C.
Guest verified by HomeToGo

We enjoyed our stay and will return. I think you need to know that your cleaning service is not doing a very thorough job. After walking on the floor for a few hours our white socks were filthy dirty.

Reviewed on 4/23/2025 | Family
Condo Kissimmee
from $133 per night
HomeToGo
Condo ∙ 6 guests ∙ 2 bedrooms
4.6
Excellent(69 ratings)
Kissimmee, Osceola County, Florida, United States
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Daniel A.
Guest verified by HomeToGo

We enjoyed the home, pool and hot tub very much. Plenty of room and close to everything.

Reviewed on 4/3/2025 | Group
Villa Kissimmee
from $543 per night
HomeToGo
Villa ∙ 26 guests ∙ 12 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
Robert S.
Guest verified by HomeToGo

Amazing property, entire family loved every moment. Owners were first class, so responsive to every need.

Reviewed on 7/15/2024 | Family
House Kissimmee
from $488 per night
HomeToGo
House ∙ 14 guests ∙ 7 bedrooms
5.0
Outstanding(104 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Ronnie H.
Guest verified by HomeToGo

Nice place to come back to after hours at the theme parks. better than a hotal room

Reviewed on 6/25/2024 | Family
Villa Kissimmee
from $219 per night
HomeToGo
Villa ∙ 8 guests ∙ 4 bedrooms
4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Terry O.
Guest verified by HomeToGo

A few changes can be made. Master bath...a roach crawled up from the left sink drain. Master shower head needs to be replaced. Put a bathmat by sink on left as you enter. We could not find extra white trash bags for kitchen trash cans. We couldn't find more toilet paper or dish washing soap.

Reviewed on 4/14/2024 | Family
House Kissimmee
from $316 per night
HomeToGo
House ∙ 12 guests ∙ 5 bedrooms
4.6
Excellent(44 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Micalyn B.
Guest verified 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 $235 per night
HomeToGo
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(22 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Stephen L.
Guest verified by HomeToGo

It should be added in description that this unit is right near a busy road with quite a bit of traffic noise..other than that it was good...if you want to relax by the pool and have quiet it may not be ideal

Reviewed on 2/18/2024 | Couple
Apartment Kissimmee
from $292 per night
HomeToGo
Apartment ∙ 9 guests ∙ 4 bedrooms
4.3
Very good(82 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Alicia D.
Guest verified by HomeToGo

Great, except the pool was freezing and we couldn't get In using our code, EVER!

Reviewed on 2/6/2024 | Family
House Kissimmee
from $296 per night
HomeToGo
House ∙ 11 guests ∙ 5 bedrooms
4.9
Outstanding(7 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
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Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

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 (22,788)
  • WiFi (26,685)
  • Air conditioning (25,117)
  • Kitchen (26,120)
  • Parking (1,717)
  • Washing machine (21,241)
  • TV (23,214)
  • Dishwasher (15,980)
  • Grill (7,547)
  • Pet-friendly (3,297)
  • Microwave (20,049)
  • Balcony/patio (6,063)

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 $558 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 (12/27 – 1/3). During this week, a night will cost on average $649. Conversely, the cheapest average prices are in a week of October (10/18 – 10/25).

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 May (5/2 – 5/9), where only 17% rentals are available. The week with the most available rentals is in August (8/30 – 9/6), with 52% 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.

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

Information about vacation rentals in Kissimmee

🏡 Vacation rentals available 28,841 rentals
🌙 Nightly prices starting at $96
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 3,303 homes
🏊 Vacation rentals with pools 22,838 homes
1,798,761 reviews
Kissimmee vacation rentals have an average rating of 4.3/5 on 1,798,761 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Kissimmee?

We found 28,841 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 11% 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 $96.

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