Vacation rentals in Kissimmee - HomeToGo base64Hash Vacation rentals in Kissimmee - HomeToGo

Vacation rentals in Kissimmee

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Top 15 Recommended vacation rentals in Kissimmee

Find your perfect vacation rental in Kissimmee from just $28 per night!

Resort Kissimmee
-42%
Jan 24 - Jan 31
Free cancellation
Resort ∙ 127 guests ∙ 2 bedrooms

Resort with pool, BBQ & jacuzzi | Suitable for remote work

Kissimmee, Osceola County, Florida, United States
$170$99
per night
Excellent
$170$99
per night
View deal
Resort Kissimmee
Jul 7 - Jul 14
Free cancellation
Resort ∙ 4 guests ∙ 1 bedroom

Family-friendly lovely resort with pool

Kissimmee, Osceola County, Florida, United States
$155
per night
Very good
$155
per night
View deal
House Kissimmee
-72%
May 10 - May 17
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly house with pool

Kissimmee, Osceola County, Florida, United States
$419$118
per night
Excellent
$419$118
per night
View deal
House Kissimmee
-70%
May 10 - May 17
House ∙ 14 guests ∙ 6 bedrooms

Vacation home with pool

Kissimmee, Osceola County, Florida, United States
$347$104
per night
Excellent
$347$104
per night
View deal
Resort Kissimmee
-16%
Jun 14 - Jun 21
Free cancellation
Resort ∙ 127 guests ∙ 1 bedroom

Resort with pool

Kissimmee, Osceola County, Florida, United States
$205$173
per night
Excellent
$205$173
per night
View deal
Resort Kissimmee
May 10 - May 17
Resort ∙ 127 guests ∙ 1 bedroom

Resort with pool | Pets are welcome

Kissimmee, Osceola County, Florida, United States
$22
per night
$22
per night
View deal
Condo Kissimmee
-62%
Aug 16 - Aug 23
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool & hot tub

Kissimmee, Osceola County, Florida, United States
$161$62
per night
Excellent
$161$62
per night
View deal
House Kissimmee
-64%
May 3 - May 10
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented beautiful house with pool | Pet-friendly

Kissimmee, Osceola County, Florida, United States
$162$58
per night
Excellent
$162$58
per night
View deal
Resort Kissimmee
Jun 12 - Jun 19
Resort ∙ 127 guests ∙ 4 bedrooms

Resort with garden, pool & terrace | Suitable for remote work | Pets are welcome

Kissimmee, Osceola County, Florida, United States
$103
per night
Very good
$103
per night
View deal
House Kissimmee
-27%
Jun 6 - Jun 13
House ∙ 12 guests ∙ 6 bedrooms

Vacation home with pool & barbecue

Kissimmee, Osceola County, Florida, United States
$348$255
per night
Outstanding
$348$255
per night
View deal
House Kissimmee
Apr 26 - May 3
House ∙ 24 guests ∙ 12 bedrooms

House with garden, private pool & grill

Kissimmee, Osceola County, Florida, United States
$243
per night
$243
per night
View deal
House Kissimmee
-67%
May 10 - May 17
House ∙ 15 guests ∙ 7 bedrooms

House with heated pool & barbeque

Kissimmee, Osceola County, Florida, United States
$412$137
per night
Good(5 ratings)
$412$137
per night
View deal
House Kissimmee
-79%
May 5 - May 12
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with private pool & patio

Kissimmee, Osceola County, Florida, United States
$468$99
per night
Excellent(8 ratings)
$468$99
per night
View deal
House Kissimmee
-32%
May 12 - May 19
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with private pool

Kissimmee, Osceola County, Florida, United States
$171$117
per night
Outstanding(4 ratings)
$171$117
per night
View deal
House Kissimmee
-57%
May 3 - May 10
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented house with hot tub & pool

Kissimmee, Osceola County, Florida, United States
$183$79
per night
Outstanding
$183$79
per night
View deal

Vacation rentals and apartments with air conditioning

House  Kissimmee
May 12 - May 19
-54%
$240
$112
per night
House ∙ 12 guests ∙ 5 bedrooms

Fully equipped vacation home with patio & private pool | Pet-friendly

4.5
Excellent(8 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
Resort  Kissimmee
May 25 - Jun 1
$137
per night
Resort ∙ 127 guests ∙ 3 bedrooms

Big resort with sauna, pool & jacuzzi | Perfect for remote work

4.2
Very good
Kissimmee, Osceola County, Florida, United States
Free cancellation
Air conditioning
View deal
House  Kissimmee
May 16 - May 23
-59%
$166
$68
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with jacuzzi & pool

Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

House  Kissimmee
Sep 20 - Sep 27
-71%
$554
$161
per night
House ∙ 20 guests ∙ 6 bedrooms

Family-oriented charming vacation home with private pool

Kissimmee, Osceola County, Florida, United States
Free cancellation
Balcony/Patio
View deal
House  Kissimmee
May 12 - May 19
-51%
$143
$70
per night
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented ample vacation home | Pets allowed

4.3
Very good(19 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
House  Kissimmee
Aug 9 - Aug 16
$126
per night
House ∙ 10 guests ∙ 4 bedrooms

House with pool, terrace & hot tub | Lake view | Suitable for remote work

4.3
Very good(40 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
See all offers

Vacation homes and rentals with a yard

House  Kissimmee
Aug 9 - Aug 16
-37%
$191
$120
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with terrace, yard & private pool

3.6
Good(92 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
House  Kissimmee
Jun 21 - Jun 28
$82
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented house with terrace, heated pool & hot tub | City view | Pets are welcome

4.0
Very good(9 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
House  Kissimmee
Jun 22 - Jun 29
$256
per night
House ∙ 12 guests ∙ 6 bedrooms

Vacation home with private pool, garden & barbecue | Lake view

5.0
Outstanding(46 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
See all offers

Best Vacation Home Deals in Kissimmee

Save up to 70%

House Kissimmee
Aug 20 - Aug 27
-49%
$580
$294
per night
House ∙ 25 guests ∙ 9 bedrooms

Child-friendly house with private pool

4.8
Outstanding(4 ratings)
Kissimmee, Osceola County, Florida, United States
Free cancellation
View deal
House Kissimmee
Jul 29 - Aug 5
-19%
$195
$159
per night
House ∙ 10 guests ∙ 5 bedrooms

House with garden, barbecue & private pool | Lake view

4.1
Very good(19 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
May 28 - Jun 4
-70%
$753
$226
per night
House ∙ 16 guests ∙ 8 bedrooms

Child-friendly lovely house with yard & private pool | Lake view | Good for workation

Kissimmee, Osceola County, Florida, United States
Free cancellation
View deal

Compare the 29,033 accommodations featured in Kissimmee and find a welcoming home for a relaxing vacation. The website HomeToGo immediately compares all of these vacation rentals so you can save up to 74%!

Budget-friendly Vacation Rentals in Kissimmee

Find Fantastic yet Inexpensive Offers

House Kissimmee
May 10 - May 17
$179
per night
House ∙ 19 guests ∙ 9 bedrooms

House with terrace, jacuzzi & private pool | Nature view

3.9
Good(15 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
Dec 19 - Dec 26
$203
per night
House ∙ 12 guests ∙ 6 bedrooms

Fully equipped house with terrace, private pool & garden | Lake view | Dogs allowed

3.2
(19 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
Jun 14 - Jun 21
$144
per night
House ∙ 9 guests ∙ 5 bedrooms

Family-friendly pleasant vacation home with garden, private pool & grill | Lake view

4.7
Excellent(146 ratings)
Kissimmee, Osceola County, Florida, United States
View deal

Top-Rated Rentals and Accommodations in Kissimmee

Book Vacation Rental Offers with the Highest User Rating

House Kissimmee
Apr 26 - May 3
$156
per night
House ∙ 12 guests ∙ 6 bedrooms

Children-friendly vacation home with terrace, private pool & sauna

5.0
Outstanding(198 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Villa Kissimmee
Apr 26 - May 3
$351
per night
Villa ∙ 18 guests ∙ 9 bedrooms

Villa with private pool, patio & hot tub

4.8
Outstanding(168 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Villa Kissimmee
Jun 7 - Jun 14
$140
per night
Villa ∙ 11 guests ∙ 5 bedrooms

Villa with barbeque, terrace & private pool | Lake view

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

Customer ratings and reviews

How are reviews collected?
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 $408
per night
HomeToGo
Villa ∙ 26 guests ∙ 12 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 $142
per night
HomeToGo
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
Omar B.
Guest verified by HomeToGo

The area location of this townhome is safe as it is a gated community, however, on several nights there was a long line of cars waiting to enter the gates, and one night we had to wait for over 10 minutes to enter the property. The house is nicely decorated and modern, with very comfortable rooms and beds. the pool is small, more like an oversized jacuzzi, and even though the description of the property says that it is a heated pool, there is a charge of $40.00 per day to heat the pool. The kitchen was clean and well-equipped, however, we did see a few unwanted insects, I reported to the property management team and they were ready to take care of the problem. communication with the property management team was good and fast.

Reviewed on 12/8/2024 | Family
House Kissimmee
from $224
per night
HomeToGo
House ∙ 10 guests ∙ 4 bedrooms
4.0
Very good(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
Kathryn C.
Guest verified by HomeToGo

There were several issues with this home upon checking in, BUT the management company was super accommodating on getting the issues resolved quickly so we could enjoy our family vacation!

Reviewed on 12/2/2024 | Family
Villa Kissimmee
from $251
per night
HomeToGo
Villa ∙ 16 guests ∙ 8 bedrooms
4.0
Very good(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 $357
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 $181
per night
HomeToGo
Villa ∙ 8 guests ∙ 4 bedrooms
4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Kissimmee

  • Pool (23,155)
  • WiFi (27,000)
  • Pet-friendly (3,337)
  • Air conditioning (25,520)
  • Kitchen (26,526)
  • TV (23,599)
  • Washing machine (19,640)
  • Hot tub (7,842)
  • Parking (1,835)
  • Microwave (20,326)
  • Grill (7,534)
  • Dishwasher (16,216)

Finding a property with a pool shouldn't be too hard in Kissimmee. More than two-thirds of the accommodations have pools. In addition, more House rental have pools than any other type of property. They are a great choice if you go in a group of 8, as that is the number of people they can welcome on average. one-third of Kissimmee's accommodations including a pool are situated within two miles 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

The price graph will give you the average nightly price for the upcoming months of the year in Kissimmee. Prices are higher in December and reach an average of $492 per night (12/27 – 1/3), making it the most expensive time to book an accommodation in Kissimmee. Prices are more affordable in September (9/20 – 9/27).

Rental availability information in Kissimmee

Find out the percentage of available rentals in Kissimmee over the next twelve months with the graph above. More people travel to Kissimmee a week in April (4/4 – 4/11). So far, 80% of the rentals are occupied this week. Conversely, it is in September (9/6 – 9/13) that the highest percentage of rentals are available.

Stay at a Kissimmee Vacation Rental for an Unforgettable Family Trip

Located directly between St. Cloud and Disney World, Kissimmee is a popular stop for vacationers headed to the Disney World theme parks. This popular central Florida destination beckons with its sunny skies, gastronomic delights, theme parks and family-centered activities.

Since Disney World opened in 1971, the town is primarily visitor-oriented and does a great job of it. Book your Kissimmee vacation rental for the perfect, adrenalin-filled adventure with the family.

What are the best activities for families in Kissimmee?

Theme Park Adventures: A Dream Vacation for Kids

Kids will love Kissimmee. Take them down to the Green Meadows Petting Farm where hands-on guided tours will introduce them to over 300 species of animals. The Paddling Center at Shingle Creek meanwhile, offers kayaking, paddling, canoeing and camping activities. The Wild Florida Airboats & Wildlife Park is a place to hang out with the sloths, bobcats and lemurs, and see alligators in the wild.

Learn how chocolate miraculously transitions from a humble bean into a luscious chocolate bar at Chocolate Kingdom. The Happy Days Family Fun Center in Kissimmee's Old Town boasts the world's largest indoor bumper car ride, as well as laser tag. At the LEGOLAND Florida Resort, adults and children alike are blown away by the structures built from LEGO blocks.

Kissimmee packs a punch, so go on and book a house with a pool to relax at the end of the day. Your first port-of-call to Florida awaits.

What are the top sights in Kissimmee?

Sights and Sounds of Kissimmee

Kissimmee's Old Town is wonderful to stroll around for its many shops, restaurants, and bars. You will also be able to check out the Ferris wheel and a classic car show held over the weekends. From late February through early April, catch some Major League Baseball at the Osceola County Stadium.

For insights into the restoration of WW2 aircrafts to working condition, visit the Warbird Air Museum. The Osceola County Historical Society is a traditional village and museum which features an interesting cracker house and horse stables. History buffs will enjoy a visit to the Museum of Military History which features the history of the American military experience through fun interactive exhibits.

Where are the unique attractions in Kissimmee?

Excursion Destinations Galore

While in Kissimmee, a day trip to Walt Disney World Resort becomes an obligation! Come and discover the fantasy and magic of your favorite Disney characters. To take a look at what a real movie set looks like, your next stop should be the Universal Orlando Resort, where you can immerse yourself in Harry Potter's magical universe, or even mount an attack on space aliens. Smaller kids will love the Ranch Buggy Tour, which takes you to one of America's oldest working cattle operations.

Just an hour’s drive from Kissimmee are the Atlantic beaches of Cape Canaveral and Cocoa Beach. Animal lovers should not miss Forever Florida, a 4,700 acre ecological ranch and wildlife conservation area that is home to alligators, black bears and the Florida panther. For bass fishing, Lake Tohopekaliga is your best bet. At the end of the day, you can unwind by the pool at your Kissimmee vacation rental and exchange stories from the day.

For something a little further afield, take a short drive to St. Cloud and visit the Peghorn National Park and Trail for great hiking and kite flying.

What are the must-see attractions in Kissimmee?

Things to Do in Kissimmee Besides Theme Parks

Museum of Military History

Find out about American military history at Kissimmee's military museum, where interactive exhibits explore American conflicts from the Civil War to the wars in Iraq and Afghanistan.

Gaylord Palms Resort and Convention Center

The glass atrium of the Gaylord Palms hotel encloses 4.5 acres of lush gardens and water features. Highlights include the luxurious spa and the organic black angus steaks in the restaurant.

Shingle Creek Regional Park

An oasis of green within the urban sprawl of Orlando, Shingle Creek can be explored by foot, bicycle or boat. Try to spot the deer, alligators and birds.

Fun Spot America

The family-owned theme park of Fun Spot America offers fun for all the family, with high-adrenaline roller coasters teamed with more gentle rides for younger children.

Kissimmee Lakefront Park

Appealing to both locals and visitors, Kissimmee Lakefront Park features wide walkways for jogging or walking, a splash park and two children's playgrounds.

Information about vacation rentals in Kissimmee

🏡 Vacation rentals available 29,033 rentals
💳 Possible discounts up to 74%
🌙 Nightly prices starting at $28
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly homes 3,289 homes
🏊 Vacation rentals with pools 23,004 homes
1,794,070 reviews
Kissimmee vacation rentals have an average rating of 4.3/5 on 1,794,070 reviews left by travelers.

Frequently Asked Questions

What is the typical price per night for a vacation home in Kissimmee?

The nightly price of accommodations in Kissimmee starts at $28. $414 is the average nightly price for house rentals in Kissimmee. Villas in Kissimmee cost on average $556 per night.

How many vacation homes are available to book in Kissimmee?

There are 29,033 vacation rentals available for booking for your vacation.

What amenities are most popular for vacation rentals in Kissimmee?

Three most popular amenities for vacation rentals in Kissimmee include accommodations that have: Pool, Internet, and Pets allowed.

How many vacation rentals with pools are in Kissimmee?

Discover 23,004 vacation rentals available in Kissimmee.

Are pets allowed in vacation rentals in Kissimmee?

In case if you are traveling with a dog in Kissimmee - 11% of vacation homes allow pets.

What's the best time to travel to Kissimmee?

If you are choosing a vacation rental in Kissimmee, keep in mind that rainy season is usually in June or July, with January often being the driest.

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