Holiday houses & accommodation in Kissimmee - HomeToGo base64Hash Holiday houses & accommodation in Kissimmee - HomeToGo

Holiday houses & accommodation in Kissimmee

Find 21,396 available holiday rentals from 125 partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • House
    • Apartment
    • Holiday park

  • Distance to centre

    • 2 km
    • 5 km
    • Any

  • Rating

    • 4.5+
    • 4+

  • Services

    • Pool
    • WiFi
    • Air conditioning
    • TV
    • Washing machine
    • Kitchen
    • Parking
    • Fireplace
    • Microwave
    • Dishwasher
    • Hot tub
    • Yard
    • Balcony/patio
    • Sauna
    • Cot
    Show more

  • Accommodation type

    • Pet-friendly
    • Wheelchair access
    • No pets
    • No smoking

  • Activities

    • Grill
    • Fishing

Top 15 Recommended holiday rentals in Kissimmee

Rent a holiday home, apartment or cottage in Kissimmee from just $107 per night!

House Kissimmee
House ∙ 6 guests ∙ 3 bedrooms

House

Kissimmee, Osceola County, Florida, United States
Charming house in Kissimmee with a private pool, kitchen, and parking for 6. Discover your perfect getaway—book your escape today!
from $124
per night
Good(29 ratings)
from $124
per night
View deal
House Kissimmee
House ∙ 8 guests ∙ 4 bedrooms

168 m² House

Kissimmee, Osceola County, Florida, United States
Stunning waterfront house in Kissimmee with a private heated pool and lakeview. Perfect for 8 guests—book your dream getaway today!
from $270
per night
Very good(19 ratings)
from $270
per night
View deal
Villa Kissimmee
Villa ∙ 6 guests ∙ 3 bedrooms

Villa

Kissimmee, Osceola County, Florida, United States
Charming villa in Kissimmee with a pool, spa, and lakeview. Perfect for families and pets. Experience relaxation—book your escape today!
from $117
per night
Excellent(86 ratings)
from $117
per night
View deal
House Kissimmee
House ∙ 11 guests ∙ 5 bedrooms

178 m² House

Kissimmee, Osceola County, Florida, United States
from $239
per night
Very good(20 ratings)
from $239
per night
View deal
Villa Kissimmee
Villa ∙ 8 guests ∙ 4 bedrooms

182 m² Villa

Kissimmee, Osceola County, Florida, United States
Relax in a stunning villa with a pool, jacuzzi, and lakeview, perfect for families. Ideal for up to 8 guests—book your getaway today!
from $337
per night
Outstanding(4 ratings)
from $337
per night
View deal
Villa Kissimmee
Villa ∙ 8 guests ∙ 4 bedrooms

172 m² Villa

Kissimmee, Osceola County, Florida, United States
Stunning villa in Kissimmee with a private heated pool, garden, and lake views. Perfect for families—book your getaway today!
from $260
per night
Outstanding(21 ratings)
from $260
per night
View deal
House Kissimmee
House ∙ 8 guests ∙ 3 bedrooms

House

Kissimmee, Osceola County, Florida, United States
Charming house in Kissimmee with a pool, fireplace, and balcony for 8. Ideal for family getaways—book your dream stay now!
from $174
per night
Outstanding(2 ratings)
from $174
per night
View deal
Villa Kissimmee
Villa ∙ 11 guests ∙ 5 bedrooms

Villa

Kissimmee, Osceola County, Florida, United States
Experience luxury in this family-friendly villa with a private heated pool, jacuzzi, and stunning lake views. Book now for an unforgettable stay!
from $198
per night
Outstanding(8 ratings)
from $198
per night
View deal
Villa Kissimmee
Villa ∙ 8 guests ∙ 4 bedrooms

149 m² Villa

Kissimmee, Osceola County, Florida, United States
Experience luxury in this family-friendly villa with a private heated pool and jacuzzi. Book now for an unforgettable Kissimmee getaway!
from $160
per night
Excellent(150 ratings)
from $160
per night
View deal
House Kissimmee
House ∙ 9 guests ∙ 4 bedrooms

House

Kissimmee, Osceola County, Florida, United States
Spacious family-friendly house in Kissimmee with a pool, jacuzzi, and pet-friendly amenities. Perfect for your next getaway—book now!
from $160
per night
Outstanding(30 ratings)
from $160
per night
View deal
Villa Kissimmee
Villa ∙ 14 guests ∙ 7 bedrooms

326 m² Villa

Kissimmee, Osceola County, Florida, United States
Experience luxury in our spacious villa with a private pool and stunning lake views. Perfect for families, book now for an unforgettable getaway!
from $360
per night
Very good(39 ratings)
from $360
per night
View deal
Villa Kissimmee
Villa ∙ 6 guests ∙ 3 bedrooms

Villa

Kissimmee, Osceola County, Florida, United States
Discover a stunning villa in Kissimmee with a heated private pool and modern kitchen, perfect for 6. Book your dream getaway today!
from $172
per night
Excellent(65 ratings)
from $172
per night
View deal
House Kissimmee
House ∙ 14 guests ∙ 6 bedrooms

279 m² House

Kissimmee, Osceola County, Florida, United States
Escape to this stunning Kissimmee house with a private heated pool, jacuzzi, and lake views. Perfect for family getaways—book your stay now!
from $303
per night
Excellent(99 ratings)
from $303
per night
View deal
House Kissimmee
House ∙ 6 guests ∙ 3 bedrooms

112 m² House

Kissimmee, Osceola County, Florida, United States
Charming house in Kissimmee with a heated pool, jacuzzi, and lakeview garden. Perfect for 6. Book now for an unforgettable getaway!
from $107
per night
Excellent(176 ratings)
from $107
per night
View deal
House Kissimmee
House ∙ 14 guests ∙ 7 bedrooms

House

Kissimmee, Osceola County, Florida, United States
Spacious house in Kissimmee with a private pool and family-friendly amenities for up to 14. Perfect for your unforgettable getaway!
from $348
per night
Very good(57 ratings)
from $348
per night
View deal

Vacation rentals and apartments with air conditioning

House Kissimmee
from $121 per night
House ∙ 8 guests ∙ 3 bedrooms

House

Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
House Kissimmee
from $145 per night
House ∙ 6 guests ∙ 4 bedrooms

House

3.7
Good(29 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
House Kissimmee
from $148 per night
House ∙ 8 guests ∙ 3 bedrooms

125 m² House

4.7
Excellent(27 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
See all offers

Best holiday homes with a patio or terrace

Villa Kissimmee
from $206 per night
Villa ∙ 8 guests ∙ 4 bedrooms

177 m² Villa

4.5
Excellent(152 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
House Kissimmee
from $297 per night
House ∙ 10 guests ∙ 5 bedrooms

262 m² House

4.4
Very good(10 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
Villa Kissimmee
from $167 per night
Villa ∙ 8 guests ∙ 4 bedrooms

Villa

Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
See all offers

Vacation homes and cottages with a garden

House Kissimmee
from $140 per night
House ∙ 7 guests ∙ 3 bedrooms

House

4.6
Excellent(22 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
House Kissimmee
from $220 per night
House ∙ 8 guests ∙ 4 bedrooms

167 m² House

4.7
Excellent(101 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
House Kissimmee
from $514 per night
House ∙ 28 guests ∙ 12 bedrooms

House

4.5
Excellent(20 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
See all offers

Budget-friendly Accommodation in Kissimmee

Find Fantastic yet Inexpensive Accommodation

House Kissimmee
from $182 per night
House ∙ 6 guests ∙ 3 bedrooms

House

4.9
Outstanding(35 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
from $241 per night
House ∙ 11 guests ∙ 5 bedrooms

House

4.9
Outstanding(316 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
from $231 per night
House ∙ 6 guests ∙ 3 bedrooms

167 m² House

4.8
Outstanding(8 ratings)
Kissimmee, Osceola County, Florida, United States
View deal

Top-Rated Accommodation in Kissimmee

Book Holiday Offers with the Highest User Rating

House Kissimmee
from $325 per night
House ∙ 12 guests ∙ 6 bedrooms

288 m² House

5.0
Outstanding(215 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Villa Kissimmee
from $143 per night
Villa ∙ 8 guests ∙ 4 bedrooms

158 m² Villa

4.9
Outstanding(127 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
from $146 per night
House ∙ 11 guests ∙ 3 bedrooms

168 m² House

4.8
Outstanding(83 ratings)
Kissimmee, Osceola County, Florida, United States
View deal

Customer ratings and reviews

How are reviews collected?
Jasmine D.
Guest verified by HomeToGo

It’s was a very nice place, only thing is they are very strict about parking my car touch the grass a lil bit and they towed my car soon as I got there

Reviewed on 08/09/2025 | Family
Villa Kissimmee
from $1,069 per night
Villa ∙ 30 guests ∙ 15 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
Julio C.
Guest verified by HomeToGo

Special thanks to Charles and Joanne Aunger from Aunger Vacation Homes who were truly gracious hosts. This stay was phenomenal. Easily accessible to all of the major theme parks and anything else you could want. Looking forward to future stays; they are first-rate.

Reviewed on 13/06/2025
House Kissimmee
from $399 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(81 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
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 26/04/2025 | Family
House Kissimmee
from $556 per night
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 23/04/2025 | Family
Condo Kissimmee
from $146 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.7
Excellent(34 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Maria V.
Guest verified by HomeToGo

Great house for a big party, everyone had their own room and was very comfortable.

Reviewed on 28/03/2025 | Family
House Kissimmee
from $329 per night
House ∙ 16 guests ∙ 8 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
Jamie K.
Guest verified by HomeToGo

We loved this rental. The location is quiet and not too far from the theme parks. The house had cute Disney touches everywhere. Our family of 3 greatly appreciated the 3 bathrooms! The screened-in porch with hot tub was wonderful after a day spent walking around theme parks.

Reviewed on 28/01/2025 | Family
House Kissimmee
from $169 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
Sarah M.
Guest verified 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 01/10/2024 | Family
House Kissimmee
from $339 per night
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding(5 ratings)
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 15/07/2024 | Family
House Kissimmee
-29%
$704
from $502 per night
House ∙ 14 guests ∙ 7 bedrooms
5.0
Outstanding(102 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Show more

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Smart search made simple

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Find your dream stay

Find your dream stay

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

Popular holiday rental amenities in Kissimmee

  • Pool (19,040)
  • WiFi (20,220)
  • Air conditioning (20,402)
  • TV (19,831)
  • Washing machine (18,149)
  • Kitchen (20,114)
  • Parking (1,529)
  • Fireplace (950)
  • Grill (7,312)
  • Microwave (16,411)
  • Dishwasher (15,316)
  • Hot tub (6,793)

Most of the accommodation options offer a pool, which makes Kissimmee an excellent holiday destination for people looking to spend their holidays poolside. Apartment rental with pools in Kissimmee are a great choice for groups of 7 and have an average cost of $656 a night. You could also rent a rental providing a pool near the water, which is the case for one-third of the rentals on offer there.

Price and Availability Index in Kissimmee

Click on any bar to see price and availability information

Holiday Rental Price Information in Kissimmee

This graph displays average prices of the holiday cottages and holiday apartments located in Kissimmee. The most expensive dates to travel to Kissimmee are in December (26/12 – 02/01). Conversely, the cheapest average prices are in a week of September (05/09 – 12/09).

Rental availability information in Kissimmee

Have a look at the above graph to see the global availability of holiday rentals in Kissimmee. The week with the highest booking rate in the next 6 months is in January (02/01 – 09/01), where 68% of the holiday lettings are booked. People tend to travel less to Kissimmee during a week in June (06/06 – 13/06) when only 35% of the rentals are booked.

Holiday Rentals & Accommodation in Kissimmee

Information about holiday rentals in Kissimmee

🏡 Holiday rentals available 21,396 rentals
🌙 Nightly prices from $107
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly lettings 3,068 properties
🏊 Holiday rentals with pools 18,888 properties
469 reviews
Kissimmee holiday lettings have an average rating of 4.1/5 across 469 reviews left by travellers.

Frequently Asked Questions

How much should I expect to pay for a holiday letting in Kissimmee?

When visiting Kissimmee, you can find holiday rentals from as little as $107 per night.

How many holiday accommodation offers will I find in Kissimmee?

There are loads of options for holiday accommodation in Kissimmee, with 21,396 offers available.

What holiday rental amenities do people typically look for when visiting Kissimmee?

The top accommodation priorities for visitors to Kissimmee are Pool, Internet and Air conditioning.

How many accommodation offers are there in Kissimmee?

You can browse 21,396 holiday lettings in Kissimmee, and find great deals from $107 per night.

Are pets permitted in holiday accommodation in Kissimmee?

Yes, there are 3,068 pet-friendly holiday rentals in Kissimmee.

Top cities to visit

Top holiday destinations in Kissimmee

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