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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sep - 14 Sep
In two months
10 Oct - 12 Oct

Browse Select Kissimmee Cottages

Lafitte's Landing Lakeview Cottage - Lakefront!
House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | Dining

Lafitte's Landing Lakeview Cottage - Lakefront!

3.0 star property
10.0 out of 10, Exceptional, (7)
"Beautiful Cottage and enjoyed the back deck overlooking the lake. Great family vacation spot."
Lafitte's Landing Lakeview Cottage - Lakefront!
8000 Lost Shaker Lane
Miscellaneous

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (7)
"The house is absolutely beautiful. Very clean and has everything you need. Unfortunately you can’t use the pool which I didn’t understand so that was the only downside. The property is gorgeous. "
8000 Lost Shaker Lane
5003 Windermere Avenue
Miscellaneous

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location, convenient to all shopping needs. Close to Disney World. Good amenities. Great for families traveling together."
5003 Windermere Avenue
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Pool

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3.0 star property
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Outdoor pool

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3.0 star property
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Modern Townhome W/private Pool & Free Water Park!
Miscellaneous

Modern Townhome W/private Pool & Free Water Park!

4.0 star property
8.8 out of 10, Excellent, (5)
"This property was excellent and lived up to the expectations in the post! So close to the parks, we came back everyday to cool down by the pool and recharge our batteries."
Modern Townhome W/private Pool & Free Water Park!
Townhome Splash Pool BBQ Free Water Park!
Miscellaneous

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (10)
"Nice and relaxing quiet neighborhood "
Townhome Splash Pool BBQ Free Water Park!
3148 Caribbean Soul Drive
Interior

3148 Caribbean Soul Drive

3.0 star property
3148 Caribbean Soul Drive
3050 Pirate Way
Miscellaneous

3050 Pirate Way

3.0 star property
3050 Pirate Way
3000 Latitude Lane
Interior

3000 Latitude Lane

3.0 star property
9.6 out of 10, Exceptional, (4)
"Great stay!"
3000 Latitude Lane
8960 Cat Palm Road
Miscellaneous

8960 Cat Palm Road

3.0 star property
10.0 out of 10, Exceptional, (1)
"Nice place to stay. Clean, quiet, secure."
8960 Cat Palm Road
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
Pool

Elegant Family Home w/ Pool, Game Room, Themed Bedrooms

3.0 star property
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
8462 Secret Key Cove
Miscellaneous

8462 Secret Key Cove

3.0 star property
8.0 out of 10, Very good, (1)
8462 Secret Key Cove
3 Mi to Disney World: Family Gem w/ Private Pool!
House (6 Bedrooms) | Front of property

3 Mi to Disney World: Family Gem w/ Private Pool!

3.0 star property
3 Mi to Disney World: Family Gem w/ Private Pool!
4718 Sleepy Hollow Drive
House (6 Bedrooms) | Property amenity

4718 Sleepy Hollow Drive

3.0 star property
2.0 out of 10, (1)
"I was highly disappointed after our stay. Our air conditioner never worked and it was inconvenient for our jam packed days to wait for someone to fix this. Really ruined our evenings."
4718 Sleepy Hollow Drive
Luxury Villa, South Facing Pool! No Rear Neighbors. Themed Rooms, Theatre & Game Room. #8so8956
Outdoor pool

Luxury Villa, South Facing Pool! No Rear Neighbors. Themed Rooms, Theatre & Game Room. #8so8956

3.0 star property
Luxury Villa, South Facing Pool! No Rear Neighbors. Themed Rooms, Theatre & Game Room. #8so8956
1888 Tropical Palms Circle
Miscellaneous

1888 Tropical Palms Circle

3.0 star property
8.0 out of 10, Very good, (2)
"My family and I had a great weekend stay at this property and the hosts were responsive and helpful. We would stay here again!"
1888 Tropical Palms Circle
Game Room & Resort Perks: Family Kissimmee Home!
House (Multiple Bedrooms) | Interior

Game Room & Resort Perks: Family Kissimmee Home!

3.0 star property
Game Room & Resort Perks: Family Kissimmee Home!
8416 Blue Lagoon Dr
Miscellaneous

8416 Blue Lagoon Dr

3.0 star property
10.0 out of 10, Exceptional, (1)
8416 Blue Lagoon Dr
Luxurious Home W/private Pool, Near Disney!
Outdoor pool

Luxurious Home W/private Pool, Near Disney!

4.0 star property
8.0 out of 10, Very good, (3)
"House was great, however chose to pay for the early check-in so we could use the pool. To use the heater for the pool it’s an up charge. Understand. However they charged me $25 per day for the entire stay but the pool wasn’t warm until the morning we checked out."
Luxurious Home W/private Pool, Near Disney!
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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Top Kissimmee Hotel Reviews

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

10/10 Excellent
"Staff very nice. Overall great stay for 5 days "
Michele 5-night trip
Posted 5 hours ago
Palazzo Lakeside Hotel

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between and per night for cottages in Kissimmee. No matter your budget, a fantastic stay is only a few clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Kissimmee?
Pick from multiple cottages in Kissimmee with a total average guest review rating of 8.8. 1702vp is a great place to relax and recharge between adventures. This 3.5-star cottage also features a swimming pool and WiFi. 4720shd Ultimate New 6 Bedroom Storey Lake Home is another leading pick with visitors to this area. It has a 4-star rating and amenities including a swimming pool and clothes washing facilities.
How many cottages are there in Kissimmee?
Choose from 748 cottages in Kissimmee. No matter if you're holidaying with the kids or organising a weekend break with your buddies, Expedia will help you find the right place to escape the hustle and bustle.