Top Cottages in Osceola County in 2026

Osceola County Cottages
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Our top choices for Osceola County cottages

Cottage in Kissimmee

Encore Swanky

3.0 star property

The price is 5.441.845 ₫

5.441.845 ₫

16.773.521 ₫ total

includes taxes & fees

1 Feb - 2 Feb

Encore Swanky

Cottage in Kissimmee

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property

9.0 out of 10, Wonderful, (15 reviews)

9.0/10

Wonderful

(15 reviews)

"As described, excellent facilities, location and price"

Anonymous traveller

Stunning Lakeview Townhome w/ Private Pool!

Cottage in Kissimmee

5003 Windermere Avenue

3.0 star property

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Great location, convenient to all shopping needs. Close to Disney World. Good amenities. Great for families traveling together."

Gary

5003 Windermere Avenue

Cottage in Kissimmee

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

Cottage in Kissimmee

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

House, Multiple Beds, Patio, Garden View (It’s A Wonderful Life) | Interior

House, Multiple Beds, Patio, Garden View (It’s A Wonderful Life) | Living area | 42-inch flat-screen TV with digital channels

Cottage in Kissimmee

It's A Wonderful Life Vacay Home

3.0 star property

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"We appreciate the space and the items provided that minimized the amount of shopping"

Valarie

It's A Wonderful Life Vacay Home

Cottage in Kissimmee

8960 Cat Palm Road

3.0 star property

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Nice place to stay. Clean, quiet, secure."

Mariano

8960 Cat Palm Road

Cottage in Kissimmee

3000 Latitude Lane

3.0 star property

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 reviews)

"Great stay!"

osiris

3000 Latitude Lane

Townhome, Multiple Beds, Patio, Garden View (Caribbean Dreamin) | 3 bedrooms, individually decorated, individually furnished, bed sheets

Townhome, Multiple Beds, Patio, Garden View (Caribbean Dreamin) | Dining

Townhome, Multiple Beds, Patio, Garden View (Caribbean Dreamin) | Private kitchen | Fridge, microwave, oven, stovetop

Cottage in Kissimmee

Caribbean Dreamin Vibrant Margaritaville Resort

3.0 star property

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"All around great environment "

Jaynelle

Caribbean Dreamin Vibrant Margaritaville Resort

Cottage in Kissimmee

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

Cottage in Indian Point

Heated Pool & Bathtub 4BR Near Disney

3.0 star property

Heated Pool & Bathtub 4BR Near Disney

Cottage in Kissimmee

8462 Secret Key Cove

3.0 star property

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

8462 Secret Key Cove

Cottage in Kissimmee

3148 Caribbean Soul Drive

3.0 star property

3148 Caribbean Soul Drive

Cottage in Kissimmee

4718 Sleepy Hollow Drive

3.0 star property

2.0 out of 10, (1 review)

2.0/10

(1 review)

"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."

Laura

4718 Sleepy Hollow Drive

Cottage in Windsor Hills

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

3.0 star property

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

Cottage, Multiple Beds, Pool Access | Pool | Outdoor pool

Cottage in Kissimmee

Sea Jules at Margaritaville

3.0 star property

6.0 out of 10, (2 reviews)

6.0/10

(2 reviews)

"Thank you. We had a great time. Highly recommended!"

Marifel

Sea Jules at Margaritaville

Villa (Star Stay at Championsgate Resort by ) | Exterior

Cottage in Champions Gate

Star Stay at Championsgate Resort by Shine Villas 023

2.0 star property

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Excellent communication. Property was immaculate. Management was very easy to deal with and made our stay very comfortable and pleasant."

Robert

Star Stay at Championsgate Resort by Shine Villas 023

Cottage in Country Creek Estates

Enchanting House few min Away From the Parks 52

3.0 star property

Enchanting House few min Away From the Parks 52

Cottage in Kissimmee

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

3.0 star property

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

House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | Living area | 42-inch flat-screen TV with digital channels, TV

House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | 3 bedrooms, individually decorated, individually furnished, desk

Cottage in Kissimmee

Lafitte's Landing Lakeview Cottage - Lakefront!

3.0 star property

9.2 out of 10, Wonderful, (12 reviews)

9.2/10

Wonderful

(12 reviews)

"We really enjoyed our stay, the home was so clean and comfortable.. "

Geraldine

Lafitte's Landing Lakeview Cottage - Lakefront!

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

Parkway International Resort

10/10 Excellent

"Great stay with kids"

Jessica 2-night trip

Posted 1 day ago

Parkway International Resort

Ramada by Wyndham Kissimmee Gateway

10/10 Excellent

"Hotel is nice, clean, and definitely worthy of a low cost hotel for a Disney trip. Great location, easy going staff. We stayed in the Tower, and that was great. Definitely feel better after staying here! Some of the reviews were worrisome, but we had a great stay! "

Michael 3-night trip

Posted 1 day ago

Ramada by Wyndham Kissimmee Gateway

Margaritaville Resort Orlando

10/10 Excellent

"the rooms are spotless."

Juan Manuel 1-night trip

Posted 1 day ago

Margaritaville Resort Orlando

Kompose Boutique Resort at Theme Parks

10/10 Excellent

"Modern facility. Spacious, modern rooms. Tasteful decor. Great location. Safe. "

Glenn 1-night trip

Posted 1 day ago

Kompose Boutique Resort at Theme Parks

Silver Lake Resort

10/10 Excellent

"Very spacious and comfortable room. the room had everything we need to have lunch and dinner inside and not have to waste money on junk food during our trip. the staff was nice and accommodating. will definitely be back. thank you ! "

Cora 2-night trip

Posted 2 days ago

Silver Lake Resort

Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent

"Very clean. Staff were very friendly. Really like how there’s an area where you can order food plus the bar. There was a buffet section for breakfast in AM till 10 and dinner at 6 PM. "

Mayelin 2-night trip

Posted 2 days ago

Holiday Inn Resort Kissimmee by the Parks by IHG

Destiny Palms Hotel Maingate West

10/10 Excellent

"Spotless room, staff was incredible. This was a terrific find and value for a perfect Disney World location."

Stephen 6-night trip

Posted 3 days ago

Destiny Palms Hotel Maingate West

Vacation Village Orlando, Celebration

10/10 Excellent

"Very nice property to stay at"

chris 2-night trip

Posted 3 days ago

Vacation Village Orlando, Celebration

Seasons Florida Resort

10/10 Excellent

"Stayed because it is not far to the airport "

Gail 1-night trip

Posted 3 days ago

Seasons Florida Resort

Find out more about Osceola County

Osceola County Cottages information

Number of reviews	40
Accommodation	897 Cottages
Lowest Price	16.773.521 ₫
Highest Price	16.773.521 ₫

Cottages in Osceola County

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Osceola County cottages

Cottage in Kissimmee

Cottage in Kissimmee

Cottage in Kissimmee

Cottage in Kissimmee

Cottage in Kissimmee

Cottage in Kissimmee

Cottage in Kissimmee

Cottage in Kissimmee

Cottage in Kissimmee

Cottage in Kissimmee

Cottage in Indian Point

Cottage in Kissimmee

Cottage in Kissimmee

Cottage in Kissimmee

Cottage in Windsor Hills

Cottage in Kissimmee

Cottage in Champions Gate

Cottage in Country Creek Estates

Cottage in Kissimmee

Cottage in Kissimmee

Find holiday rentals that suit your style

Top Osceola County Hotel Reviews

Parkway International Resort

Find out more about Osceola County

Osceola County Cottages information