Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Book Faster

Property Type

Apartments
Bungalows
Condos
Cottages
Estates
Hotels
Homes
Townhomes
Villas
Barns
Boats
Cabins
Castles
Chalets
Farmhouses
Lodges
Studios
Yachts

Book Faster

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Save time when booking: choose rentals that accept online reservations or online payments

Kissimmee Area Vacation Rentals(3,008)

3,008 Results
$166 - $229
per night
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
(12)
$69 - $239
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(10)
  • 6 BR,
  • 4 BA,
  • Sleeps 16
3 - 7 night minimum stay
(37)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
3 night minimum stay
(174)
  • 7 BR,
  • 6 BA,
  • Sleeps 16
7 night minimum stay
(47)
$120 - $179
per night
5 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
5 - 7 night minimum stay
(28)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
3 - 7 night minimum stay
(20)
$230 - $520
per night
4 - 6 night minimum stay
  • 7 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 18
4 - 6 night minimum stay
(8)
$2,205 - $3,395
per week
7 - 21 night minimum stay
  • 7 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 16
7 - 21 night minimum stay
(11)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
4 night minimum stay
(80)
$145 - $190
per night
3 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
(31)
$79 - $149
per night
4 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 5 night minimum stay
(65)
$314 - $429
per night
3 - 14 night minimum stay
  • 7 BR,
  • 6 BA,
  • Sleeps 16
3 - 14 night minimum stay
(20)
$99 - $149
per night
6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
6 night minimum stay
(43)
$1,595 - $2,295
per week
7 night minimum stay
  • 6 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 14
7 night minimum stay
(31)
  • 5 BR,
  • 5 BA,
  • Sleeps 12
5 - 7 night minimum stay
(56)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
3 - 4 night minimum stay
(71)
  • 5 BR,
  • 4 BA,
  • Sleeps 12
4 - 7 night minimum stay
(9)
$1,295 - $1,715
per week
7 - 14 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 - 14 night minimum stay
(66)
$199 - $425
per night
3 - 7 night minimum stay
  • 7 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 16
3 - 7 night minimum stay
(15)
  • 7 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
3 - 14 night minimum stay
(30)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(12)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 - 10 night minimum stay
(39)
  • 6 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 14
3 - 7 night minimum stay
(12)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 - 10 night minimum stay
(46)
  • 3 BR,
  • 3 BA,
  • Sleeps 10
2 - 5 night minimum stay
(68)
$165 - $230
per night
3 - 14 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 - 14 night minimum stay
(36)
$150 - $200
per night
5 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
5 - 7 night minimum stay
(67)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
3 night minimum stay
(44)
$84 - $119
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(5)
Advertisement

Kissimmee Area

 

Recent Kissimmee Area Reviews

Wonderful Place to Stay

5 of 5
My family of 13 just completed a two week stay in this beautifully appointed villa called Knights Castle. My room was the king en suite downstairs and it was very comfortable. The rest of the bedrooms are upstairs and a word of caution here. Don’t shut the doors as this throws off the flow of air and some of the rooms can get very warm. Another tip is to be sure you bring along some slippers for the rooms that are not carpeted. While those floors are easier to keep clean that way, my feet were frozen until I decided to pick up an inexpensive pair. The other thing we noticed as we walked in was that the rooms feel or seem much smaller than are pictured on the website. I’m guessing they may have been taken with a wide angle lens to get everything in, but in just a day we settled into a cozy place where we could bond without getting lost. You will also notice several improvements, i.e. kitchen appliances are all black and I personally loved the Samsung refrigerator. This resort seems like it was built for more rental investments than full time residents as many of the homes are very close together and parking on the street can be crazy at times. The Wi-Fi is very strong throughout the house. It accommodated everyone on their Smartphone’s and tablets. The free Home Away App is kind of nice to have as it lists many things available locally. If you like to prepare meals the kitchen has the basic utensils and we are offering a list to the owner of additions that might benefit it in the future. Theme parks are very close to this resort and there are plenty of stores, restaurants and souvenir shops for those that need them. The patio/lanai is great and the pool, while on the small side, accommodated a 6 man water polo game a time or two. The water was crystal clear, the spa warm to hot when turned on and we know pool staff was out twice to add chemicals and clean it while we were there. The alarm on the patio door was very loud and effective in keeping the two year old at bay. It even worked on the college kids when they forgot to disengage it. Manager, Kim, was very friendly and informative when we needed her help and the resort staff was very helpful on trash/recycling days with putting containers curbside and then returning them to their resting places. So if you are looking for a unit for a large group, look no further. We highly recommend the house, owner and manager. Happy holiday to everyone.
  • Submitted: Dec 17, 2014
  • Stayed: Nov 2014

AMAZING LOCATION AND PROPERTY!

5 of 5
Bill's condo was an absolute pleasure to stay for our Disney World vacation! It perfectly accommodated six adults, as each couple had their own room. We took advantage of the available kitchen and cookware, cooking our own meals! The location cannot be beat, as the condo is only a ten minute drive to Disney World. In addition, there are nearby restaurants and a Super Target in very close proximity. I would love to stay here again on our visit to Orlando. Thanks, Bill!
  • Submitted: Nov 25, 2014
  • Stayed: Nov 2014

Fabulous Holidayin Florida

5 of 5
We are regulator visitors to Florida and selected this location after a lot of research. The Emerald Island Resort is the best location that we have stayed at so far. It is very close to Disney, especially to Animal Kingdom and Blizzard Beach using the shortcut via Sherberth Road. Also the Intestate 4 is close by offering easy access to Seaworld and Universal. The house was situated on a well maintained and pleasant road and was a great place to chill out in between going to the theme parks. The beds were comfortable and we had plenty of space and we never felt on top of each other. The pool area was not overlooked at the rear and there was plenty of furniture as we spent a lot of time around the pool, eating our breakfast outside every day and enjoying many an evening drink. We spent some time by the Clubhouse pool and bar for a change. All the staff that we met were pleasant and helpful and we managed to book on line tickets using the free computers. We felt very safe at this resort and felt that the security is very good. The resort feels very select and private but is so close to the 192 and virtually every restaurant franchise that you can of, is within a 5-10 minute drive. There is also a Winn Dixie Supermarket which is really well stocked about a 2 minute drive from the resort. We all enjoyed our stay at this resort and house and would return here again for a future holiday.
  • Submitted: Nov 1, 2014
  • Stayed: Oct 2014