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

Houses & Vacation Rentals in Kissimmee

Find 29,092 available house rentals from 107 partners
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Top 15 Recommended vacation rentals in Kissimmee

Find your perfect vacation rental in Kissimmee from just $41 per night!

Resort Kissimmee
-17%
Mar 29 - Apr 5
Resort ∙ 4 guests ∙ 1 bedroom

Family-friendly lovely resort with pool

Kissimmee, Osceola County, Florida, United States
$269$208
per night
Very good
$269$208
per night
View deal
Resort Kissimmee
-28%
May 3 - May 10
Free cancellation
Resort ∙ 127 guests ∙ 2 bedrooms

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

Kissimmee, Osceola County, Florida, United States
$186$154
per night
Excellent
$186$154
per night
View deal
Resort Kissimmee
-33%
May 27 - Jun 3
Resort ∙ 127 guests ∙ 1 bedroom

Resort with hot tub, pool & sauna

Kissimmee, Osceola County, Florida, United States
$398$210
per night
Very good
$398$210
per night
View deal
Resort Kissimmee
-21%
Mar 27 - Apr 3
Resort ∙ 127 guests ∙ 1 bedroom

Children-friendly lovely resort with pool | Good for workation

Kissimmee, Osceola County, Florida, United States
$270$174
per night
Excellent
$270$174
per night
View deal
Resort Kissimmee
Mar 15 - Mar 22
Free cancellation
Resort ∙ 127 guests ∙ 1 bedroom

Resort with pool | Pets are welcome

Kissimmee, Osceola County, Florida, United States
$42
per night
$42
per night
View deal
House Kissimmee
-62%
Mar 15 - Mar 22
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with jacuzzi & pool

Kissimmee, Osceola County, Florida, United States
$245$113
per night
$245$113
per night
View deal
House Kissimmee
-34%
May 3 - May 10
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped lovely house with private pool

Kissimmee, Osceola County, Florida, United States
$209$175
per night
Outstanding(15 ratings)
$209$175
per night
View deal
Condo Kissimmee
-34%
Apr 26 - May 3
Condo ∙ 10 guests ∙ 3 bedrooms

Condo with sauna, hot tub & pool

Kissimmee, Osceola County, Florida, United States
$178$114
per night
Excellent
$178$114
per night
View deal
House Kissimmee
-70%
Sep 20 - Sep 27
House ∙ 8 guests ∙ 4 bedrooms

House with pool & jacuzzi

Kissimmee, Osceola County, Florida, United States
$368$135
per night
Outstanding(54 ratings)
$368$135
per night
View deal
Condo Kissimmee
-45%
Apr 12 - Apr 19
Condo ∙ 6 guests ∙ 2 bedrooms

Family-oriented condo with hot tub, heated pool & sauna

Kissimmee, Osceola County, Florida, United States
$151$108
per night
Excellent(29 ratings)
$151$108
per night
View deal
House Kissimmee
Mar 15 - Mar 22
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with pool & hot tub

Kissimmee, Osceola County, Florida, United States
$141
per night
Outstanding
$141
per night
View deal
House Kissimmee
-58%
Mar 12 - Mar 19
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with jacuzzi, pool & grill

Kissimmee, Osceola County, Florida, United States
$282$141
per night
Very good
$282$141
per night
View deal
House Kissimmee
-20%
Sep 13 - Sep 20
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace, yard & private pool

Kissimmee, Osceola County, Florida, United States
$194$137
per night
Excellent(65 ratings)
$194$137
per night
View deal
House Kissimmee
-33%
Sep 20 - Sep 27
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented charming vacation home with terrace, private pool & garden

Kissimmee, Osceola County, Florida, United States
$191$157
per night
Excellent(32 ratings)
$191$157
per night
View deal
House Kissimmee
-58%
Mar 16 - Mar 23
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with private pool & patio

Kissimmee, Osceola County, Florida, United States
$315$150
per night
Excellent(8 ratings)
$315$150
per night
View deal

Vacation rentals and apartments with air conditioning

House  Kissimmee
Jun 9 - Jun 16
-27%
$250
$203
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with private pool

5.0
Outstanding(4 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
House  Kissimmee
May 7 - May 14
-60%
$242
$126
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
Air conditioning
View deal
House  Kissimmee
Jun 19 - Jun 26
$227
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with private pool, hot tub & patio | Nature view

5.0
Outstanding(2 ratings)
Kissimmee, Osceola County, Florida, United States
Air conditioning
View deal
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Apartments With Balconies or Patios

House  Kissimmee
Sep 16 - Sep 23
-77%
$781
$227
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
Villa  Kissimmee
Jan 6 - Jan 13
-29%
$219
$173
per night
Villa ∙ 8 guests ∙ 4 bedrooms

Villa with private pool, grill & jacuzzi | Nature view

4.6
Excellent(137 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
House  Kissimmee
Mar 29 - Apr 5
$155
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with patio, barbecue & private pool

4.4
Very good(85 ratings)
Kissimmee, Osceola County, Florida, United States
Balcony/Patio
View deal
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Vacation homes and rentals with a yard

House  Kissimmee
Sep 8 - Sep 15
-67%
$545
$187
per night
House ∙ 8 guests ∙ 4 bedrooms

House with yard, private pool & BBQ | Perfect for remote work

Kissimmee, Osceola County, Florida, United States
Free cancellation
Yard
View deal
House  Kissimmee
Jan 3 - Jan 10
$178
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with yard, private pool & barbecue | Nature view

4.8
Outstanding(222 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
House  Kissimmee
Sep 6 - Sep 13
$266
per night
House ∙ 14 guests ∙ 5 bedrooms

Vacation home with jacuzzi, garden & private pool | Lake view | Suitable for remote work

4.9
Outstanding(22 ratings)
Kissimmee, Osceola County, Florida, United States
Yard
View deal
See all offers

Best Vacation Home Deals in Kissimmee

Save up to 68%

House Kissimmee
Oct 27 - Nov 3
-68%
$1,281
$415
per night
House ∙ 24 guests ∙ 12 bedrooms

Children-friendly vacation home with BBQ, jacuzzi & private pool | Dogs allowed

4.5
Excellent(2 ratings)
Kissimmee, Osceola County, Florida, United States
Free cancellation
View deal
House Kissimmee
Jun 14 - Jun 21
-24%
$181
$138
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with private pool

5.0
Outstanding(4 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
Mar 29 - Apr 5
-51%
$153
$76
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with private pool

Kissimmee, Osceola County, Florida, United States
View deal

Compare the 29,092 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 72%!

Budget-friendly Vacation Rentals in Kissimmee

Find Fantastic yet Inexpensive Offers

House Kissimmee
Mar 6 - Mar 13
-57%
$212
$124
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home with Patio & Pool

5.0
Outstanding(58 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
House Kissimmee
Apr 26 - May 3
-53%
$199
$113
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-Friendly Pleasant Vacation Home with Pool | Pet-Friendly

4.5
Excellent
Kissimmee, Osceola County, Florida, United States
View deal
Villa Kissimmee
Apr 26 - May 3
$131
per night
Villa ∙ 8 guests ∙ 4 bedrooms

Fully Equipped Nice Villa with Pool, Sauna & Barbeque | Pets Are Welcome

4.8
Outstanding(123 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
Sep 27 - Oct 4
$154
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with heated pool, garden & hot tub | Lake view

4.9
Outstanding(281 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
Villa Kissimmee
Jan 10 - Jan 17
-38%
$475
$334
per night
Villa ∙ 12 guests ∙ 6 bedrooms

Family-oriented villa with BBQ, private pool & hot tub | Water view

4.8
Outstanding(62 ratings)
Kissimmee, Osceola County, Florida, United States
Free cancellation
View deal
Apartment Kissimmee
Sep 6 - Sep 13
-75%
$335
$108
per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Child-friendly apartment with pool, barbeque & hot tub

4.9
Outstanding(26 ratings)
Kissimmee, Osceola County, Florida, United States
Free cancellation
View deal

Customer ratings and reviews

How are reviews collected?
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 $155
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 $204
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 $245
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 $369
per night
HomeToGo
House ∙ 14 guests ∙ 7 bedrooms
5.0
Outstanding(103 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 $162
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 $229
per night
HomeToGo
House ∙ 12 guests ∙ 5 bedrooms
4.6
Excellent(44 ratings)
Kissimmee, Osceola County, Florida, United States
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
-6%
$110
from $104
per night
HomeToGo
Condo ∙ 4 guests ∙ 2 bedrooms
4.6
Excellent(64 ratings)
Kissimmee, Osceola County, Florida, United States
View deal
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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 (23,286)
  • WiFi (26,906)
  • Pet-friendly (3,325)
  • Air conditioning (25,650)
  • Kitchen (26,396)
  • TV (23,559)
  • Washing machine (19,153)
  • Hot tub (8,835)
  • Parking (1,888)
  • Microwave (20,369)
  • Grill (7,510)
  • Dishwasher (16,252)

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 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 $504 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 December (12/6 – 12/13). So far, 78% of the rentals are occupied this week. Conversely, it is in May (5/3 – 5/10) 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 29,092 rentals
💳 Possible discounts up to 72%
🌙 Nightly prices starting at $41
⭐ Popular amenities Pool, Internet and Pets allowed
🐾 Pet friendly homes 3,361 homes
🏊 Vacation rentals with pools 23,315 homes
1,846,906 reviews
Kissimmee vacation rentals have an average rating of 4.3/5 on 1,846,906 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 $41. $413 is the average nightly price for house rentals in Kissimmee. Villas in Kissimmee cost on average $553 per night.

How many vacation homes are available to book in Kissimmee?

There are 29,092 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 23,315 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.

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