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Featured Cottages in Kissimmee

Our top choices for Kissimmee cottages

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

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

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

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

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!

4.0 star property
8.8 out of 10, Excellent, (5)
"Place was in great location. "
Modern Townhome W/private Pool & Free Water Park!

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (10)
"Is good for the all the family "
Townhome Splash Pool BBQ Free Water Park!

3148 Caribbean Soul Drive

3.0 star property
3148 Caribbean Soul Drive

3050 Pirate Way

3.0 star property
3050 Pirate Way

3000 Latitude Lane

3.0 star property
9.6 out of 10, Exceptional, (4)
"Great stay!"
3000 Latitude Lane

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

Enchanted Cottage with Pool and Mini-Golf Near Disney

9.2 out of 10, Wonderful, (21)
"Very comfortable place. The area where the property is located is very quite and relaxing"
Enchanted Cottage with Pool and Mini-Golf Near Disney

Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

The price is AU$405
includes taxes & fees
31 Aug - 1 Sept
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

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

3.0 star property
8.0 out of 10, Very good, (1)
8462 Secret Key Cove

Brilliant Cottage near Disney with Private Pool & Margaritaville Resort &.

Brilliant Cottage near Disney with Private Pool & Margaritaville Resort &.

Gorgeous Cottage w/Private Pool *Near Disney!*

9.2 out of 10, Wonderful, (5)
"Love the neighborhood and rental. Perfect location."
Gorgeous Cottage w/Private Pool *Near Disney!*

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

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

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

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

Frequently asked questions

How much do cottages in Kissimmee cost?
Prepare to pay between AU$405 and AU$405 per night for cottages in Kissimmee. Whatever your budget, an excellent stay is only a click or two away on Expedia. This price was 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.
How many cottages are there in Kissimmee?
Pack your bags and pick from 1050 cottages in Kissimmee. Thinking about a place where you can relax and stay in touch with nature? Expedia will help you find the ideal escape in a few easy clicks.
What is there to do in Kissimmee near my cottage?
Whatever you're into, Kissimmee has loads to keep you occupied. Discovery Cove, Aquatica and Disneys Typhoon Lagoon Water Park are on most visitors' itineraries. Don't miss Gatorland®, Medieval Times and Fun Spot America either. With Expedia's hotel deals in Kissimmee, you'll be able to see more terrific attractions like these with the cash you save.