A lake with a wooden bridge and a gazebo.

Cottages in Osceola County

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Osceola County cottages

A two-story house with a stone foundation, a front porch, and a well-maintained lawn.

1. Encore Swanky

Encore Swanky
3.0 star property
Kissimmee
3.6 out of 10, (4 reviews)
"Ck in was at 4pm. Place wasn't ready till 5:15. Place was clean. Pool was dirty n cold. Had to pay to have it heated. 1st day it was still cold. So only got 1 day of heated pool.place was kinda run down as well. Fire alarms kept beeping. Communication could have been better as well. It wasn't terrible, but wouldn't stay here again. "
United States
Christine
Encore Swanky
Property amenity

2. 3050 Pirate Way

3050 Pirate Way
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
3050 Pirate Way
Exterior

3. It's A Wonderful Life Vacay Home

It's A Wonderful Life Vacay Home
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"We appreciate the space and the items provided that minimized the amount of shopping"
United States
Valarie
It's A Wonderful Life Vacay Home
A covered outdoor seating area with a sofa, chairs, and a table.

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

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
3.0 star property
Kissimmee
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
A covered outdoor seating area with a sofa, chairs, and a table.

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

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
3.0 star property
Kissimmee
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Exterior

6. Frankly Fintastic Happy Days in Margaritaville!

Frankly Fintastic Happy Days in Margaritaville!
3.5 star property
Kissimmee
8.8 out of 10, Excellent, (3 reviews)
"The property was very nice, the rooms are very nice and clean. I would stay there again without any doubt."
United States
Fabio
Frankly Fintastic Happy Days in Margaritaville!
A two-story building with a red-tiled roof, numbered 107 and 109, and a small porch with steps leading to the entrance.

7. 109 Pompano Beach Drive

109 Pompano Beach Drive
3.0 star property
Kissimmee
109 Pompano Beach Drive
Property amenity

8. 8000 Lost Shaker Lane

8000 Lost Shaker Lane
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (9 reviews)
"Lots of room , beautifully decorated. Close to everything we needed for the weekend . "
United States
alina
8000 Lost Shaker Lane
A modern building with a stone facade, a covered patio, and a well-maintained garden with palm trees.

9. Spacious 6 Bed Home With Pool in Storey Lake

Spacious 6 Bed Home With Pool in Storey Lake
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (6 reviews)
"We had an amazing time we love visiting the area would absolutely rent again"
United States
Mychal
Spacious 6 Bed Home With Pool in Storey Lake
A two-story house with a garage, stone foundation, and a driveway.

10. Chic 8BR All Suites With Pool and Game Room

Chic 8BR All Suites With Pool and Game Room
4.0 star property
Kissimmee
Chic 8BR All Suites With Pool and Game Room
A two-story residential building with a garage, a driveway, and a well-maintained lawn.

11. Chic Luxury Haven - Unforgettable Retreat

Chic Luxury Haven - Unforgettable Retreat
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (3 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. The host was friendly, responsive, and made the whole process easy. The location was convenient, and I had everything I needed for a relaxing stay. I would definitely stay here again and highly recommend this to anyone looking for a great place to stay."
United States
Chris
Chic Luxury Haven - Unforgettable Retreat
An aerial view of a residential area with a swimming pool complex, a basketball court, and a road with vehicles.

12. 5003 Windermere Avenue

5003 Windermere Avenue
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"Great location, convenient to all shopping needs. Close to Disney World. Good amenities. Great for families traveling together."
United States
Gary
5003 Windermere Avenue
An aerial view of a residential area with a swimming pool complex, a basketball court, and a road with vehicles.

13. 4177 Paragraph Drive

4177 Paragraph Drive
3.0 star property
Kissimmee
4177 Paragraph Drive
An aerial view of a residential area with a swimming pool complex, a basketball court, and a road with vehicles.

14. Lakeview Home w/ Private Pool & Free Water Park!

Lakeview Home w/ Private Pool & Free Water Park!
3.5 star property
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"The location is fantastic. The house was clean and welcoming. Communication was fantastic!"
United States
Tricia
Lakeview Home w/ Private Pool & Free Water Park!
A two-story residential building with a garage, a driveway, and a well-maintained lawn with trees and shrubs.

15. Lakeview 7BR Getaway, Pool, Great Location

Lakeview 7BR Getaway, Pool, Great Location
4.0 star property
Crystal Cove
4.0 out of 10, (1 review)
"very surface level cleaning, carpets stains, seating pool area was very dirty, beds were not comfortable and did not seem sturdy at all. garage had a unpleasant smell. my family did not enjoy would not stay again."
United States
Isabella
Lakeview 7BR Getaway, Pool, Great Location
A glass-enclosed patio with a pool, outdoor seating, and a view of buildings in the background.

16. 8960 Cat Palm Road

8960 Cat Palm Road
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Nice place to stay. Clean, quiet, secure."
Mexico
Mariano
8960 Cat Palm Road
Property amenity

17. 1570 Sandbagger Drive

1570 Sandbagger Drive
3.0 star property
Champions Gate
1570 Sandbagger Drive
A two-story house with a garage, a front lawn, and palm trees.

18. 3 Mi to Wdw: Windsor Hills Home w/ Game Room!

3 Mi to Wdw: Windsor Hills Home w/ Game Room!
3.0 star property
Windsor Hills
3 Mi to Wdw: Windsor Hills Home w/ Game Room!
A swimming pool with a hot tub, surrounded by a covered patio with brick flooring and a view of houses in the background.

19. Spacious 5br, Private Pool, Beautiful Decor

Spacious 5br, Private Pool, Beautiful Decor
3.0 star property
Champions Gate
Spacious 5br, Private Pool, Beautiful Decor
A covered outdoor seating area with a sofa, chairs, and a table.

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

Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
3.0 star property
Kissimmee
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
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 Osceola County Hotel Reviews

Legacy Vacation Resorts - Kissimmee/Orlando

Legacy Vacation Resorts - Kissimmee/Orlando

8/10 Good
"overall ok , the water pressure sucks but ok"
Tamra 2-night trip
Posted less than an hour ago
Legacy Vacation Resorts - Kissimmee/Orlando

Find out more about Osceola County

Osceola County Cottages information

Number of reviews
26
Accommodation
1413 Cottages
Lowest Price
Highest Price