Kissimmee Vacation Rentals - HomeToGo base64Hash Kissimmee Vacation Rentals - HomeToGo

Kissimmee Vacation Rentals

Find 21,411 available home rentals from 113 partners
Anytime
Guests
Anytime
Guests

  • Price per night

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

  • Accommodation types

    • House
    • Apartment
    • Resort

  • Distance to center

    • 2 km
    • 5 km
    • Any

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

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

  • Accommodation type

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

  • Activities

    • Grill
    • Fishing

Top 15 Recommended vacation rentals in Kissimmee

Find your perfect vacation rental in Kissimmee from just $110 per night!

Villa Kissimmee
Villa ∙ 8 guests ∙ 3 bedrooms

121 m² Villa

Kissimmee, Osceola County, Florida, United States
This villa in Kissimmee features a pool, sauna, spa, and jacuzzi, accommodating up to 8 guests with pet-friendly options.
from $159
per night
Outstanding(167 ratings)
from $159
per night
View deal
House Kissimmee
House ∙ 29 guests ∙ 14 bedrooms

592 m² House

Kissimmee, Osceola County, Florida, United States
This spacious house rental in Kissimmee boasts a private heated pool, lakeview balcony, and family-friendly amenities for 29 guests.
from $761
per night
Very good(10 ratings)
from $761
per night
View deal
Villa Kissimmee
Villa ∙ 26 guests ∙ 12 bedrooms

446 m² Villa

Kissimmee, Osceola County, Florida, United States
This villa in Kissimmee features a heated pool, kitchen, and parking, accommodating up to 26 guests for an unforgettable getaway.
from $546
per night
Excellent(9 ratings)
from $546
per night
View deal
House Kissimmee
House ∙ 12 guests ∙ 6 bedrooms

288 m² House

Kissimmee, Osceola County, Florida, United States
This Kissimmee house rental features a private heated pool, sauna, jacuzzi, and space for 12, perfect for family getaways.
from $312
per night
Outstanding(215 ratings)
from $312
per night
View deal
Villa Kissimmee
Villa ∙ 8 guests ∙ 4 bedrooms

149 m² Villa

Kissimmee, Osceola County, Florida, United States
This Kissimmee villa features a private heated pool, jacuzzi, and a kitchen, perfect for families seeking a memorable getaway.
from $149
per night
Excellent(150 ratings)
from $149
per night
View deal
House Kissimmee
House ∙ 8 guests ∙ 3 bedrooms

House

Kissimmee, Osceola County, Florida, United States
This Kissimmee house rental features a private pool, fireplace, jacuzzi, and kitchen, accommodating up to 8 guests for an unforgettable stay.
from $220
per night
Outstanding(40 ratings)
from $220
per night
View deal
House Kissimmee
House ∙ 11 guests ∙ 5 bedrooms

House

Kissimmee, Osceola County, Florida, United States
This house rental in Kissimmee features a private pool, yard, and kitchen, accommodating up to 11 guests and pets.
from $230
per night
Outstanding(314 ratings)
from $230
per night
View deal
House Kissimmee
House ∙ 8 guests ∙ 3 bedrooms

125 m² House

Kissimmee, Osceola County, Florida, United States
This Kissimmee house rental features a heated pool, kitchen, and pet-friendly options for up to 8 guests, perfect for families.
from $133
per night
Excellent(27 ratings)
from $133
per night
View deal
House Kissimmee
House ∙ 9 guests ∙ 4 bedrooms

House

Kissimmee, Osceola County, Florida, United States
This house rental in Kissimmee features a pool, jacuzzi, and a kitchen, accommodating up to 9 guests and pets welcome.
from $151
per night
Outstanding(29 ratings)
from $151
per night
View deal
House Kissimmee
House ∙ 12 guests ∙ 6 bedrooms

313 m² House

Kissimmee, Osceola County, Florida, United States
This Kissimmee house rental offers a private heated pool, jacuzzi, and spacious yard, perfect for family gatherings of up to 12.
from $217
per night
Excellent(175 ratings)
from $217
per night
View deal
Villa Kissimmee
Villa ∙ 8 guests ∙ 4 bedrooms

Villa

Kissimmee, Osceola County, Florida, United States
This villa in Kissimmee features a pool, sauna, fireplace, and spa, accommodating up to 8 guests for a perfect getaway.
from $175
per night
from $175
per night
View deal
Villa Kissimmee
Villa ∙ 6 guests ∙ 3 bedrooms

Villa

Kissimmee, Osceola County, Florida, United States
This Kissimmee villa features a private heated pool, a kitchen, and ample space for six, perfect for your next getaway.
from $162
per night
Excellent(65 ratings)
from $162
per night
View deal
House Kissimmee
House ∙ 6 guests ∙ 3 bedrooms

167 m² House

Kissimmee, Osceola County, Florida, United States
This Kissimmee house rental features a private heated pool, jacuzzi, and a family-friendly yard, perfect for a memorable getaway.
from $217
per night
Outstanding(8 ratings)
from $217
per night
View deal
House Kissimmee
House ∙ 6 guests ∙ 4 bedrooms

House

Kissimmee, Osceola County, Florida, United States
This family-friendly house rental in Kissimmee accommodates 6 guests, features a kitchen, and welcomes pets with convenient parking.
from $135
per night
Good(29 ratings)
from $135
per night
View deal
Condo Kissimmee
Condo ∙ 6 guests ∙ 3 bedrooms

113 m² Condo

Kissimmee, Osceola County, Florida, United States
This Kissimmee condo for six features a pool, kitchen, jacuzzi, and parking, perfect for a memorable vacation getaway.
from $125
per night
Very good(111 ratings)
from $125
per night
View deal

Vacation rentals and apartments with air conditioning

House Kissimmee
from $214 per night
House ∙ 8 guests ∙ 4 bedrooms

House

3.8
Good(18 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
House Kissimmee
from $178 per night
House ∙ 6 guests ∙ 3 bedrooms

House

4.9
Outstanding(35 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
Villa Kissimmee
from $233 per night
Villa ∙ 8 guests ∙ 4 bedrooms

182 m² Villa

5.0
Outstanding(4 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
See all offers

Apartments with a balcony or patio

Villa Kissimmee
from $195 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 $214 per night
House ∙ 8 guests ∙ 4 bedrooms

House

4.7
Excellent(75 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
House Kissimmee
from $206 per night
House ∙ 8 guests ∙ 4 bedrooms

167 m² House

4.7
Excellent(99 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
See all offers

Vacation homes and cottages with a garden

House Kissimmee
from $149 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 $251 per night
House ∙ 12 guests ∙ 5 bedrooms

204 m² House

5.0
Outstanding(75 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
House Kissimmee
from $326 per night
House ∙ 18 guests ∙ 7 bedrooms

290 m² House

4.8
Outstanding(94 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
See all offers

Budget-friendly Rentals in Kissimmee

Find Fantastic yet Inexpensive Rentals

House Kissimmee
from $146 per night
House ∙ 6 guests ∙ 3 bedrooms

House

4.8
Outstanding(8 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
from $164 per night
House ∙ 8 guests ∙ 3 bedrooms

House

5.0
Outstanding(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
from $364 per night
House ∙ 14 guests ∙ 7 bedrooms

265 m² House

4.6
Excellent(98 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 $162 per night
House ∙ 8 guests ∙ 4 bedrooms

177 m² House

4.9
Outstanding(155 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
from $138 per night
House ∙ 11 guests ∙ 3 bedrooms

168 m² House

4.8
Outstanding(83 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Villa Kissimmee
from $570 per night
Villa ∙ 16 guests ∙ 8 bedrooms

2888 m² Villa

4.9
Outstanding(37 ratings)
Kissimmee, Osceola County, Florida, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Kissimmee

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 9/8/2025 | Family
Villa Kissimmee
from $842 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 6/13/2025
House Kissimmee
from $372 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 4/26/2025 | Family
House Kissimmee
from $537 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 4/23/2025 | Family
Condo Kissimmee
from $138 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 3/28/2025 | Family
House Kissimmee
from $312 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 1/28/2025 | Family
House Kissimmee
from $168 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 10/1/2024 | Family
House Kissimmee
from $318 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 7/15/2024 | Family
House Kissimmee
from $471 per night
House ∙ 14 guests ∙ 7 bedrooms
5.0
Outstanding(101 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Show more

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

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

Smart search made simple

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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 (18,692)
  • WiFi (19,901)
  • Air conditioning (20,054)
  • Kitchen (19,742)
  • Parking (1,514)
  • Washing machine (17,873)
  • TV (19,495)
  • Dishwasher (14,992)
  • Grill (7,207)
  • Pet-friendly (3,123)
  • Microwave (16,090)
  • Balcony/patio (5,259)

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 $612 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 (12/26 – 1/2). During this week, a night will cost on average $696. Conversely, the cheapest average prices are in a week of October (10/17 – 10/24).

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 (9/5 – 9/12), where only 27% rentals are available. The week with the most available rentals is in March (3/14 – 3/21), with 60% 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 21,411 rentals
🌙 Nightly prices starting at $110
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 3,152 homes
🏊 Vacation rentals with pools 18,908 homes

Frequently Asked Questions

What is the typical availability of vacation rentals in Kissimmee?

We found 21,411 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 15% 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 $110.

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