Houses & Vacation Rentals in Kissimmee - HomeToGo base64Hash Houses & Vacation Rentals in Kissimmee - HomeToGo

Houses & Vacation Rentals in Kissimmee

Find 29,365 available offers from 106 partners
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Recommended vacation rentals in Kissimmee

Find your perfect vacation rental in Kissimmee from just $69 per night!

Resort Kissimmee
-39%
Jan 11 - Jan 18
Free cancellation
Resort ∙ 127 guests ∙ 2 bedrooms

Resort with Jacuzzi, BBQ & Pool | Good for Workation

Kissimmee, Osceola County, Florida, United States
$211$134
per night
Excellent
$211$134
per night
View deal
Resort Kissimmee
-27%
May 17 - May 24
Free cancellation
Resort ∙ 127 guests ∙ 3 bedrooms

Big Resort with Hot Tub, Pool & Sauna | Suitable for Remote Work

Kissimmee, Osceola County, Florida, United States
$223$148
per night
Very good
$223$148
per night
View deal
Resort Kissimmee
-35%
May 14 - May 21
Resort ∙ 127 guests ∙ 4 bedrooms

Resort with Pool, Yard & Terrace | Perfect for Remote Work | Pet-Friendly

Kissimmee, Osceola County, Florida, United States
$185$133
per night
Very good
$185$133
per night
View deal
Resort Kissimmee
-20%
Mar 29 - Apr 5
Free cancellation
Resort ∙ 127 guests ∙ 1 bedroom

Resort with Pool

Kissimmee, Osceola County, Florida, United States
$172$142
per night
Excellent
$172$142
per night
View deal
Villa Kissimmee
Feb 1 - Feb 8
Villa ∙ 10 guests ∙ 5 bedrooms

Children-Friendly Lovely Villa with Private Pool & Terrace

Kissimmee, Osceola County, Florida, United States
$225
per night
Outstanding(40 ratings)
$225
per night
View deal
Resort Kissimmee
-26%
Mar 30 - Apr 6
Free cancellation
Resort ∙ 127 guests ∙ 1 bedroom

Resort with Hot Tub, Pool & Sauna

Kissimmee, Osceola County, Florida, United States
$315$223
per night
Excellent
$315$223
per night
View deal
House Kissimmee
-82%
Apr 30 - May 7
House ∙ 14 guests ∙ 6 bedrooms

Family-Friendly Vacation Home with Grill & Private Pool | Good for Workation

Kissimmee, Osceola County, Florida, United States
$657$333
per night
Very good(65 ratings)
$657$333
per night
View deal
Resort Kissimmee
-32%
Feb 21 - Feb 28
Free cancellation
Resort ∙ 8 guests ∙ 1 bedroom

Resort with BBQ, Pool & Jacuzzi

Kissimmee, Osceola County, Florida, United States
$158$108
per night
Very good
$158$108
per night
View deal
Villa Kissimmee
Apr 22 - Apr 29
Villa ∙ 16 guests ∙ 7 bedrooms

Fully Equipped Villa with Grill, Yard & Private Pool

Kissimmee, Osceola County, Florida, United States
$624
per night
Outstanding(128 ratings)
$624
per night
View deal
Villa Kissimmee
Jan 6 - Jan 13
Villa ∙ 26 guests ∙ 9 bedrooms

Villa with Patio, Garden & Barbeque | City View

Kissimmee, Osceola County, Florida, United States
$1,022
per night
Outstanding(60 ratings)
$1,022
per night
View deal
House Kissimmee
Jan 4 - Jan 11
House ∙ 10 guests ∙ 5 bedrooms

Fully Equipped Nice Vacation Home with BBQ & Pool | Pet-Friendly

Kissimmee, Osceola County, Florida, United States
$334
per night
Outstanding(1 rating)
$334
per night
View deal
House Kissimmee
-58%
Jan 19 - Jan 26
House ∙ 14 guests ∙ 5 bedrooms

House with Private Pool, Barbecue & Garden | Lake View | Perfect for Remote Work

Kissimmee, Osceola County, Florida, United States
$652$254
per night
Outstanding(19 ratings)
$652$254
per night
View deal
House Kissimmee
-42%
Dec 6 - Dec 13
House ∙ 10 guests ∙ 4 bedrooms

House with Patio & Private Pool

Kissimmee, Osceola County, Florida, United States
$333$217
per night
Excellent(31 ratings)
$333$217
per night
View deal
House Kissimmee
-32%
Oct 4 - Oct 11
House ∙ 8 guests ∙ 4 bedrooms

Children-Friendly Vacation Home with Patio, Heated Pool & Yard | City View | Pets Allowed

Kissimmee, Osceola County, Florida, United States
$190$151
per night
Very good(7 ratings)
$190$151
per night
View deal
House Kissimmee
-31%
Sep 20 - Sep 27
House ∙ 15 guests ∙ 7 bedrooms

Vacation Home with Private Pool & Barbecue | Lake View

Kissimmee, Osceola County, Florida, United States
$555$401
per night
Outstanding(15 ratings)
$555$401
per night
View deal

Vacation homes and rentals with a yard

House  Kissimmee
Jan 11 - Jan 18
$206
per night
House ∙ 8 guests ∙ 4 bedrooms

House with Private Pool, Grill & Yard | Lake View

4.9
Outstanding(261 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
Condo  Kissimmee
Jan 11 - Jan 18
$128
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Pool, Yard & Grill

5.0
Outstanding(2 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
House  Kissimmee
Dec 2 - Dec 9
-34%
$652
$254
per night
House ∙ 14 guests ∙ 5 bedrooms

House with Private Pool, Barbecue & Garden | Lake View | Perfect for Remote Work

4.9
Outstanding(19 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
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Vacation rentals and apartments with air conditioning

House  Kissimmee
Jul 13 - Jul 20
$156
per night
House ∙ 6 guests ∙ 4 bedrooms

Vacation Home with Private Pool

5.0
Outstanding(10 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
House  Kissimmee
Jan 11 - Jan 18
$235
per night
House ∙ 14 guests ∙ 7 bedrooms

House with Barbecue & Private Pool

4.6
Excellent(37 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
Resort  Kissimmee
Jun 9 - Jun 16
-49%
$185
$133
per night
Resort ∙ 127 guests ∙ 4 bedrooms

Resort with Pool, Yard & Terrace | Perfect for Remote Work | Pet-Friendly

4.2
Very good
Kissimmee, Osceola County, Florida, United States
Free cancellation
Air conditioning
View deal
See all offers

Apartments With Balconies or Patios

House  Kissimmee
May 24 - May 31
$155
per night
House ∙ 8 guests ∙ 4 bedrooms

House with Patio, Barbeque & Private Pool

4.5
Excellent(84 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
House  Kissimmee
Dec 2 - Dec 9
$158
per night
House ∙ 8 guests ∙ 4 bedrooms

House with Yard, Private Pool & Patio

4.7
Excellent(64 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
Villa  Kissimmee
Dec 2 - Dec 9
$166
per night
Villa ∙ 8 guests ∙ 4 bedrooms

Villa with Private Pool, Yard & Patio | Lake View

4.7
Excellent(113 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
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Best Vacation Home Deals in Kissimmee

Save up to 73%

Condo Kissimmee
Jan 8 - Jan 15
-72%
$247
$69
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with Pool & Jacuzzi

5.0
Outstanding
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
May 10 - May 17
-73%
$308
$83
per night
House ∙ 10 guests ∙ 4 bedrooms

House with Grill, Pool & Terrace | Lake View | Perfect for Remote Work

4.3
Very good(38 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
Jan 8 - Jan 15
-61%
$275
$107
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully Equipped Beautiful Vacation Home with Heated Pool

5.0
Outstanding(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal

Compare the 29,365 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 57%!

Budget-friendly Vacation Rentals in Kissimmee

Find Fantastic yet Inexpensive Offers

House Kissimmee
Mar 22 - Mar 29
$179
per night
House ∙ 8 guests ∙ 3 bedrooms

House with Private Pool

5.0
Outstanding(4 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Resort Kissimmee
Mar 29 - Apr 5
$186
per night
Resort ∙ 10 guests ∙ 1 bedroom

Family-Friendly Wonderful Resort with Pool

4.4
Very good
Kissimmee, Osceola County, Florida, United States
Free cancellation
View deal
House Kissimmee
Sep 6 - Sep 13
$192
per night
House ∙ 14 guests ∙ 5 bedrooms

Children-Friendly Vacation Home with Private Pool, Sauna & Patio | Pets Are Welcome

5.0
Outstanding(62 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

Villa Kissimmee
Aug 9 - Aug 16
$134
per night
Villa ∙ 10 guests ∙ 5 bedrooms

Villa with Patio & Heated Pool | Nature View

4.9
Outstanding(107 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Villa Kissimmee
Jan 18 - Jan 25
$165
per night
Villa ∙ 7 guests ∙ 3 bedrooms

Family-Friendly Villa with Private Pool & Grill

5.0
Outstanding(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Villa Kissimmee
Nov 8 - Nov 15
$377
per night
Villa ∙ 16 guests ∙ 7 bedrooms

Family-Friendly Big Villa with Garden, Patio & Grill | Nature View

4.8
Outstanding(7 ratings)
Kissimmee, Osceola County, Florida, United States
View deal

Customer ratings and reviews

How are reviews collected?
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 $194
per night
HomeToGo
House ∙ 10 guests ∙ 4 bedrooms
4.0
Very good(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
from $194
per night
House ∙ 10 guests ∙ 4 bedrooms
4.0
Very good(1 rating)
Kissimmee, Osceola County, Florida, United States
HomeToGo
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 $202
per night
HomeToGo
Villa ∙ 16 guests ∙ 8 bedrooms
4.0
Very good(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
from $202
per night
Villa ∙ 16 guests ∙ 8 bedrooms
4.0
Very good(1 rating)
Kissimmee, Osceola County, Florida, United States
HomeToGo
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 $229
per night
HomeToGo
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
View deal
from $229
per night
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding(1 rating)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Vickie H.
Guest verified by HomeToGo

The house was big enough and accommodated all our Board members. But there were a few issues.

Reviewed on 9/8/2024 | Group
House Kissimmee
from $270
per night
HomeToGo
House ∙ 20 guests ∙ 10 bedrooms
4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $270
per night
House ∙ 20 guests ∙ 10 bedrooms
4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Christina G.
Guest verified 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
from $219
per night
HomeToGo
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(86 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $219
per night
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(86 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
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 $171
per night
HomeToGo
Villa ∙ 8 guests ∙ 4 bedrooms
4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $171
per night
Villa ∙ 8 guests ∙ 4 bedrooms
4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Danielle M.
Guest verified by HomeToGo

The home was just as described (except the couch in the living room is different than the picture but no big deal!). We had enough towels and linens and everyone had plenty of space. The owners were prompt with messaging when we had questions and we got the access codes before our trip. We all felt the house was a great value!

Reviewed on 5/30/2024 | Family
House Kissimmee
from $208
per night
HomeToGo
House ∙ 12 guests ∙ 5 bedrooms
4.0
Very good(2 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $208
per night
House ∙ 12 guests ∙ 5 bedrooms
4.0
Very good(2 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
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 $230
per night
HomeToGo
House ∙ 12 guests ∙ 5 bedrooms
4.6
Excellent(44 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $230
per night
House ∙ 12 guests ∙ 5 bedrooms
4.6
Excellent(44 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
Jackie P.
Guest verified by HomeToGo

This was a great place for 3 of us ladies to get away. The price was right and the unit was just what we had hoped for. The complex was very well taken care of and the pool was beautiful (except it was not heated and too cold to swim).

Reviewed on 4/9/2024 | Group
Condo Kissimmee
from $109
per night
HomeToGo
Condo ∙ 4 guests ∙ 2 bedrooms
4.6
Excellent(61 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
from $109
per night
Condo ∙ 4 guests ∙ 2 bedrooms
4.6
Excellent(61 ratings)
Kissimmee, Osceola County, Florida, United States
HomeToGo
View deal
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Find your dream stay

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

Popular Rental Amenities in Kissimmee

  • Pool (23,352)
  • WiFi (27,352)
  • Pet-friendly (3,520)
  • Air conditioning (25,592)
  • Kitchen (26,558)
  • TV (23,715)
  • Washing machine (19,079)
  • Hot tub (5,781)
  • Parking (2,313)
  • Microwave (20,672)
  • Grill (8,245)
  • Dishwasher (16,458)

Finding a property with a pool shouldn't be too hard in Kissimmee. Most 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 7, 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 $551 per night (12/20 – 12/27), making it the most expensive time to book an accommodation in Kissimmee. Prices are more affordable in August (8/30 – 9/6).

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 September (9/6 – 9/13). So far, 79% of the rentals are occupied this week. Conversely, it is in October (10/4 – 10/11) 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 29,365 rentals
💳 Possible discounts up to 57%
🌙 Nightly prices starting at $69
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly homes 3,502 homes
🏊 Vacation rentals with pools 23,479 homes
1,850,466 reviews
Kissimmee vacation rentals have an average rating of 4.3/5 on 1,850,466 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 $69. $407 is the average nightly price for house rentals in Kissimmee. Villas in Kissimmee cost on average $526 per night.

How many vacation homes are available to book in Kissimmee?

There are 29,365 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 23,479 vacation rentals available in Kissimmee.

Are pets allowed in vacation rentals in Kissimmee?

In case if you are traveling with a dog in Kissimmee - 12% 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.

Find the perfect Kissimmee home to match your style

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