Search Vacation Homes in Kissimmee

Most properties are fully refundable. Because flexibility matters.

Save 10% or more on over 100,000 hotels worldwide as a One Key member.

Search over 2.9 million properties and 550 airlines worldwide.

Find properties with these dates

Tonight
May 15 - May 16
Tomorrow
May 16 - May 17
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

Compare 16117 Vacation Homes in Kissimmee with updated reviews, rates, and availability.

Sport court
4Bd W/ Pool & Close To Disney @ Encantada Resort 8570
2.0 star property
10.0 out of 10, Exceptional, (1)
"It was great! Very comfortable and convenient"
4Bd W/ Pool & Close To Disney @ Encantada Resort 8570
Outdoor pool, a heated pool
Summer Discount- Brand New Themed 9BR Home @ Disney, Private Pool/SPA, Game Room
10.0 out of 10, Exceptional, (18)
"Everybody enjoyed the stay. Check-in is smooth, owner even gave us early check-in so we could put our frozen items earlier. Location is 7 minutes from Walmart, and accessible to many restaurants in the area. Car access uses QR code and very convenient to pass the main gate entrance. Parking is restricted to 5 cars, but have additional parking at the Clubhouse. House facilities is what is advertised, with 2 large refrigerators, 2 sets of washer/dryer, which is good for large family gatherings....
Summer Discount- Brand New Themed 9BR Home @ Disney, Private Pool/SPA, Game Room
A heated pool
Outdoor TV, Air Hockey, Foosball, Epic Game Room, Basketball Arcade, 1GB: Summer Breeze
10.0 out of 10, Exceptional, (13)
"We enjoyed the friendliness of the staff the house was spacious and clean. Kyle communicates and responds back promptly. Looking to book with him more in the future"
Outdoor TV, Air Hockey, Foosball, Epic Game Room, Basketball Arcade, 1GB: Summer Breeze
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Pool
Upstay - Modern Pool Home w Games - Sleeps 18!
10.0 out of 10, Exceptional, (4)
"Great place for guys on a golf trip, everyone really enjoyed this place."
Upstay - Modern Pool Home w Games - Sleeps 18!
Outdoor pool, a heated pool
Luxury Pool Home Steps to Disney, 2 Master Suites, Gated, Game Rm, BBQ Free WiFi
10.0 out of 10, Exceptional, (88)
"I feel like we really "hit the jackpot" when we found this rental. The home is super clean, exactly as shown, and located in a central spot where it feels like you're miles away from all of the chaos, but you're really staying smack in the middle of it all. My first priority when I look for a rental is finding one with recent high cleanliness ratings. Although the home itself seems a bit older, the owner has really kept up with everything, and the cleaning crew seems to be keeping up quite...
Luxury Pool Home Steps to Disney, 2 Master Suites, Gated, Game Rm, BBQ Free WiFi
Pool
6BR Home, Prime Location
10.0 out of 10, Exceptional, (3)
"The house so Beautiful and clean. We enjoyed the pool at the house and the waterpark on the premises. It is a great house for a gathering of family and friends. I do suggest updating the mattresses. I couldn’t have asked for a better place for our large group. The check in process was easy and all my emails Were answered promptly. Thank you for your hospitality."
6BR Home, Prime Location
Outdoor pool, a heated pool
Free Waterpark, Free Heated Pool/Spa and Grill, Game/Theater Rm, & PS5
10.0 out of 10, Exceptional, (49)
"Great property within easy reach (20 mins) of Disney world entrance. Very well equipped kitchen and ample linen and towels etc. Wendy was very informative and answered all of my sometimes silly questions immediately. Check in was easy and we were provided with very detailed instructions for getting to the property and expectations for our stay. Overall a fab experience which could have only been better if we had stayed longer as 9 nights was nowhere nearly enough time to get the full Orlando...
Free Waterpark, Free Heated Pool/Spa and Grill, Game/Theater Rm, & PS5
Outdoor pool, a heated pool
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
10.0 out of 10, Exceptional, (44)
"We had such a great stay. The home is very comfortable and had all the kitchen essentials we needed. Would highly recommend."
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Outdoor pool, a heated pool
Stunning 5 Bedroom townhome in prime location- Paradise Palms resort community!
9.8 out of 10, Exceptional, (155)
"We got to Orlando early, and Tim was very accomodating. There was even a slight issue with the security letting us in due to the early arrival, and Tim hopped on the phone when them super fast and it was resolved within minutes. Would love to stay here again."
Stunning 5 Bedroom townhome in prime location- Paradise Palms resort community!
A heated pool
Drive-In Theater, Forest Bedroom, Huge Pirate Ship, Lake Views, Pool Table, Grill: Movie Magic
9.8 out of 10, Exceptional, (12)
"Amazing place , very responsive Host Everything was perfect the place is beautiful!"
Drive-In Theater, Forest Bedroom, Huge Pirate Ship, Lake Views, Pool Table, Grill: Movie Magic
A heated pool
Jurassic Game Room-2 Theaters (Inside & Poolside)
9.8 out of 10, Exceptional, (51)
"The house is nice with plenty to do. It’s close to everything and in a nice neighborhood. We played 5 different golf courses and never had more than a 30 minute drive. It could’ve been a little cleaner but nothing really to complain about. They communicate well and were really easy to work with"
Jurassic Game Room-2 Theaters (Inside & Poolside)
A heated pool
"Enchanted Escape" - 4 Massage Chairs & Peloton
9.8 out of 10, Exceptional, (8)
"Nice home with everything we needed."
"Enchanted Escape" - 4 Massage Chairs & Peloton
Pool
H2631E-Resort/Single Level POOL SPA Home Disney
9.6 out of 10, Exceptional, (14)
"We stayed the last two weeks of March 2024. We were a group of 8, ranging from 2 years to 71 years. The house was exactly as described - everyone loved it. The kids loved the games tables and the swimming pool and the adults loved the spa and the space everyone had. The resort is lovely and the location is perfect. We were there during Easter and Spring Break but never had any issues with the traffic and found getting to the Disney parks was really straightforward. Excellent communication with...
The price is $173
$599 total
includes taxes & fees
May 28 - May 29
H2631E-Resort/Single Level POOL SPA Home Disney
Outdoor pool, a heated pool
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
9.6 out of 10, Exceptional, (67)
"We loved the 5 bedroom townhouse. It was clean, spacious and having our own pool was great. Kathy checked on us, made arrival and departure so easy. The lazy River at the resort pool was awesome. We would definitely stay here again."
Windsor @ Westside 5 Bed, Private townhouse, Private Pool, Wonderful Amenities
Outdoor pool, a heated pool
Vibrant Townhome near parks!
9.6 out of 10, Exceptional, (5)
"The condo was as described and was exactly what we needed for the week!! The overall cleanliness of the condo was just ok, the pool and pool area could use some TLC. There were small mite bugs but only in the kitchen area. The resort and the location of the condo was perfect. The beds were very comfy!! We will definitely be back to this resort! Thanks!!"
Vibrant Townhome near parks!
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1411)
"Close to Disney, nice small hotel. Rooms were exactly as described, super comfortable for a family of 5. Checkout is strict but we had a late flight and they were great about accommodating us after check out time with parking. "
The Berkley, Orlando
Private pool
Formosa Valley Resort by UNE Homes
4.0 star property
9.4 out of 10, Exceptional, (112)
"Downstairs bedroom bathroom had water get too cold quickly. Upstairs master bedroom had shower that had boiling hot water. No washcloths available."
Formosa Valley Resort by UNE Homes
Water park
Splendid 5Bd Close to Disney at Storey Lake 4251
5.0 star property
9.4 out of 10, Exceptional, (3)
"Excellent property . Really clean and lots of space. Really close to Disney and plenty of restaurants a short drive away. My only complaint is the communication for check in. I got message and phone call 30 mins before check in saying if I don't fill out check in form my booking would be cancelled. This really wasn't ideal as I was driving. After I did it I received so many text and emails to help with my stay. I was getting them from several different numbers. Then 3 hrs after checking out. 4...
Splendid 5Bd Close to Disney at Storey Lake 4251
Pool
Villas At Seven Dwarfs - 4BR, 3BA, 2 ensuite king
9.2 out of 10, Wonderful, (88)
"This property was exactly as advertised. Clean and affordable in a gated community with activities to keep the kids happy. Our daily commute to the Orange County Convention Center was a breeze. The property manager was very responsive and great to work with."
Villas At Seven Dwarfs - 4BR, 3BA, 2 ensuite king
A heated pool
Spacious Family Retreat W/ Home Theater, Private Pool, Free WiFi, & Gas Grill
9.2 out of 10, Wonderful, (16)
"Great property. A few issues that didn't bother us much but would be problematic for families cooking. Dishwasher not working...very little cutlery. Pots pans and utensils limited."
Spacious Family Retreat W/ Home Theater, Private Pool, Free WiFi, & Gas Grill
Don't see what you're looking for?
See all available properties in Kissimmee
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Price trends for Vacation Homes in Kissimmee

Less expensive
More expensive
Next month
April
December
$148
Month
Price
January
$150
February
$156
March
$145
April
$114
May
$123
June
$148
July
$154
August
$131
September
$136
October
$122
November
$150
December
$207
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed Vacation Homes in Kissimmee. Select dates and complete search for nightly totals inclusive of taxes and fees.

Other property types in Kissimmee

Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (833)
"The property was very nice but we had no idea what layout we would be getting until we arrived which made it hard to plan. The villa did not come with the frozen drink machine it was supposed to have and had no extra blankets or pillows "
Margaritaville Resort Orlando Cottages by Rentyl
Exterior
Ramada by Wyndham Kissimmee Gateway
3.0 star property
7.2 out of 10, Good, (5895)
"My trip was awesome and the location was perfect "
The price is $44
$66 total
includes taxes & fees
May 16 - May 17
Ramada by Wyndham Kissimmee Gateway
Water park
Flamingo Waterpark Resort
3.0 star property
6.6 out of 10, (1143)
"The only issue was that I called to service my room 2 days before my last day and for 12pm but nothing was done so I have to grab toilet paper and towels from lobby "
The price is $70
$113 total
includes taxes & fees
Jun 6 - Jun 7
Flamingo Waterpark Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Kissimmee Vacation Homes information

Number of reviews
2,100
Accommodation
16117 Vacation Homes
Lowest Price
$173
Highest Price
$173

Recent reviews of Kissimmee hotels
Expedia verified reviews

Margaritaville Resort Orlando

Margaritaville Resort Orlando

5/5 Excellent
"It was great and very convenient that it had a strip of restaurants stores close where we could walk to do something different at night time"
A verified traveler stayed at Margaritaville Resort Orlando
Posted 20 hours ago
Margaritaville Resort Orlando