Holiday Homes in Kissimmee

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Featured Holiday Homes in Kissimmee

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1599)
"Close to Walt Disney World and very affordable. "
The Berkley, Orlando

Free Water Park! Private Pool & Game Room (7739)

8.2 out of 10, Very good, (57)
"Will stay again"
Free Water Park! Private Pool & Game Room (7739)

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (128)
"The place is beautiful, clean and Romy for a big family"
Formosa Valley Resort by UNE Homes

4 BR Home Near Disney-EXTREMELY CLEAN/WELL MAINTAINED/GREAT LOCATION!

9.6 out of 10, Exceptional, (70)
"Had 4 young adults with us, was excited for them to see game room. Only one pool stick was functional, the table tennis board was missing the arm for net, the air hockey didn’t come on, the PS only had one control and no games connected. So games room was disappointing. However everything else was 5 stars. "
4 BR Home Near Disney-EXTREMELY CLEAN/WELL MAINTAINED/GREAT LOCATION!

Encore Resort

4.0 star property
6.4 out of 10, (113)
"It was a very nice home. My family had a great time"
Encore Resort

The Bear's Den Resort Orlando

5.0 star property
8.0 out of 10, Very good, (19)
"Check-in and check-out were easy. The staff was very accommodating. The home is stunningly beautiful and clean. We loved every moment of our stay and will return!"
The Bear's Den Resort Orlando

POOL HOME - Luxury Windsor Palms Resort - 6 miles to Disney! POOL HEAT INCLUDED!

10.0 out of 10, Exceptional, (141)
"Our stay was perfect. The home has everything you need and is close to the parks. This was our 2nd stay with host Elaine. She is great to work with and we are planning next stay this spring! "
POOL HOME - Luxury Windsor Palms Resort - 6 miles to Disney! POOL HEAT INCLUDED!

Lake View! Free Waterpark! Modern 5BR- Windsor at Westside (8890GC)

7.6 out of 10, Good, (41)
"The place was nice. My friends and I enjoyed our stay. The only cons I have are the carpets (stained…feels unclean), the peeling leather (white) couch, and the mesh screening above the pools needs to get fixed (there’s a big hole). Other than that, we really enjoyed our stay. Check in/check out process was really easy and no complications. Please read before booking, if I had a chance review the Renter’s Agreement before booking, that would’ve been helpful in deciding to book this place or...
Lake View! Free Waterpark! Modern 5BR- Windsor at Westside (8890GC)

Great 3 bed/3 bath townhome in Crestwynd Bay, just 2 miles from WDW main gate

9.2 out of 10, Wonderful, (103)
"Great location...6 minutes to Disney, 3 minutes to Walmart. Everything clean, nice space. Would stay again. Gave 4 stars due to the beds. Beds were very firm/hard in all rooms. Would bring mattress toppers next time."
Great 3 bed/3 bath townhome in Crestwynd Bay, just 2 miles from WDW main gate

Amazing-Movie Theater-Private Pool/Spa-Great View-Themed Bedrooms

9.8 out of 10, Exceptional, (91)
"The house was amazing. It had plenty of room for our group of 9 and it was nice to have so many bathrooms. The backyard was nice to sit out and relax and everyone loved the pool and spa. The location of the house was perfect so close to everything and the parks. Would highly Recommend staying here will definitely book again. "
Amazing-Movie Theater-Private Pool/Spa-Great View-Themed Bedrooms

Maple Leaf Inn & Suites

2.5 star property
7.0 out of 10, Good, (59)
"Not nearly as nice as advertised. Appeared to have long term tenants. Owner was nice. All of the cats outside were cute."
The price is AU$123
includes taxes & fees
28 Nov - 29 Nov
Maple Leaf Inn & Suites

Spacious Vacation Home 20 min from Theme Parks!

9.4 out of 10, Exceptional, (30)
"Very smooth stay i had no issues with the house"
The price is AU$589
includes taxes & fees
1 Dec - 2 Dec
Spacious Vacation Home 20 min from Theme Parks!

Caribbean Dreamin | Vibrant Margaritaville Resort

9.8 out of 10, Exceptional, (9)
"The property was not just clean. It was move in ready clean. Everything was well planned and thought out. There was even an umbrella we could use for the afternoon showers. We really enjoyed our stay and there was tons to do nearby. It was a very quiet and relaxing place to stay at!!"
Caribbean Dreamin | Vibrant Margaritaville Resort

Brand New, Completely Renovated, South Facing w/ Luxurious Finishes & Updates

9.2 out of 10, Wonderful, (61)
"The condo was very nicely decorated and had all of the things we needed for our 5 day stay. Communication with the property owner/manager was prompt and very easy. The only things negative we have to say about the property are as follows: Shower heads were not sufficient for gals with thick curly hair. Some hand held shower heads might be a nice addition….at least one anyway. And sometimes there was no hot water in the kitchen sink. Two of the mattresses were very firm which might be ok for some...
Brand New, Completely Renovated, South Facing w/ Luxurious Finishes & Updates

Gorgeous 4Bd W/ Pool & Waterpark @ Storey Lake 4836M

4.0 star property
9.0 out of 10, Wonderful, (2)
"The house is very well decorated. Bedrooms are super cool with each room having its own theme. My only complaint which was a major pain is the sliding door to the pool. It constantly gets stuck and is off track. My 13 year old went out on back patio to read and got stuck outside for 30 minutes because the door wouldn’t open. I couldn’t even open it for him and had to get my husband. The door really needs to be replaced or fixed. The company is aware because the instructions to get into the home...
Gorgeous 4Bd W/ Pool & Waterpark @ Storey Lake 4836M

MO800 Champions Gate 5 Bedroom bathroom 5 Private Pool & Jaccuzi, Free Waterpark

9.0 out of 10, Wonderful, (62)
"Is nice and clean i love the place"
MO800 Champions Gate 5 Bedroom bathroom 5 Private Pool & Jaccuzi, Free Waterpark

Great Vacation Home Ideal Retreat in the Heart of the Disney area

9.6 out of 10, Exceptional, (164)
"Excellent overall will be staying again and again"
Great Vacation Home Ideal Retreat in the Heart of the Disney area

Dog-friendly townhome w/ private pool & resort water park - close to Disney

8.0 out of 10, Very good, (45)
"Everything was good pool had"
Dog-friendly townhome w/ private pool & resort water park - close to Disney

Villa The Dreamers , ultra modern villa , 3 miles from Disney , pool

9.6 out of 10, Exceptional, (168)
"We really liked this property. The kids enjoyed the pool, and they said the water park was ok. (They just prefered the pool at the house.) Beds were comfortable, and so were the pillows. Communication was easy, and we got swift replies to any email we sent. The only thing I suggest is, whoever cleans, have them deep clean a little more. The couch had crumbs in between the seat cushions, and the floors had some dirt stains. I thought the tiles had some knicks, but i looked closer it was dirt...
Villa The Dreamers , ultra modern villa , 3 miles from Disney , pool

Sophisticated 4 En Suites w/ Private Hot Tub

9.8 out of 10, Exceptional, (9)
"Everything was as advertised. Place was very clean and modern. Very nice accommodations. Would definitely stay there again."
Sophisticated 4 En Suites w/ Private Hot Tub
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.
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Other property types in Kissimmee

Seralago Hotel & Suites Main Gate East

3.0 star property
5.2 out of 10, (5565)
"Wow! SeraLago has definitely stepped up their rooms. We stayed in the new suites and had plenty of room for 3 adults. Separated bedroom, living room and kitchen area. I would suggest coffee maker and a comfy chair but everything else was great for the price."
The price is AU$100
includes taxes & fees
28 Nov - 29 Nov
Seralago Hotel & Suites Main Gate East

Ramada by Wyndham Hotel & Water Park

3.0 star property
6.8 out of 10, (1298)
"The perfect size waterpark for families with kids. Good value. "
The price is AU$176
includes taxes & fees
1 Dec - 2 Dec
Ramada by Wyndham Hotel & Water Park

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1084)
"Very pretty, and spacious- but a bit far from the resort "
Margaritaville Resort Orlando Cottages by Rentyl
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.
Beautiful view of the beach with palm trees

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