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Compare 995 Cottages in Kissimmee with updated reviews, rates, and availability.

Large Villa W/private Pool & Game Room! Waterpark

3.5 star property
9.6 out of 10, Exceptional, (11)
"Great property! Was perfect for our family and made down time from the parks really nice."
Large Villa W/private Pool & Game Room! Waterpark

Home w/ Hot Tub: 4 Mi to Disney!

9.4 out of 10, Exceptional, (30)
"Family friendly home. We stayed here for a multi family trip to Disney. We especially love that there were two primary rooms with king beds and on suites. The house has all the necessities in the kitchen, with coffee /keurig combo , cups and plates, and other cookie necessities. Very comfortable and specious stay and would highly recommend. "
Home w/ Hot Tub: 4 Mi to Disney!

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

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

1 bedroom, private laundry in resort near Disney!!

9.2 out of 10, Wonderful, (127)
"The stay was great and the location was perfect! The area felt very safe and it was easy to get to. We were doing a lot of different activities on this trip and it was a nice relaxing stay. "
1 bedroom, private laundry in resort near Disney!!

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.4 out of 10, Very Good, (9)
"Perfect location house was just what is described "
Stunning Lakeview Townhome w/ Private Pool!

4 miles from Disney 5 Star RV Resort! Location Location !The Hidden Gem Cottage!

9.8 out of 10, Exceptional, (24)
"Everything was super clean and great service "
4 miles from Disney 5 Star RV Resort! Location Location !The Hidden Gem Cottage!

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (9)
"Nice and relaxing quiet neighborhood "
Townhome Splash Pool BBQ Free Water Park!

Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly

9.6 out of 10, Exceptional, (5)
"The house was very clean and the area offered lots of dining options which were in walking distance. The only thing that I would recommend is to provide more towels. "
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly

6 Br / 4,5 Bath + Pool/Spa + Game Room / Less than 4 miles from Disney

9.6 out of 10, Exceptional, (9)
"Great location in a quiet gated community near Disney as well as grocery stores etc. House was big and spacious, with all appliances needed, and lots of beds & bathrooms. Only downside was that the cold weather made for very little pool time!"
6 Br / 4,5 Bath + Pool/Spa + Game Room / Less than 4 miles from Disney

Once Upon a Lime – Margaritaville 3 BDR Sleeps 9! Incredible Amenities

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great property. Very clean!"
Once Upon a Lime – Margaritaville 3 BDR Sleeps 9! Incredible Amenities

3000 Latitude Lane

3.0 star property
10.0 out of 10, Exceptional, (3)
"We loved this property the moment we walked in. We enjoyed the comfy beds, coziness, close parking, easy check-in, cleanliness, and having our own hot tub. We would like to stay here, again."
3000 Latitude Lane

3148 Caribbean Soul Drive

3.0 star property
3148 Caribbean Soul Drive

Spacious Vacation Rental w/ Yard in Kissimmee!

3.0 star property
8.0 out of 10, Very Good, (1)
"Communication on the property was excellent. Comfortable"
Spacious Vacation Rental w/ Yard in Kissimmee!

Enchanting House few min Away From the Parks 52

3.0 star property
Enchanting House few min Away From the Parks 52

8462 Secret Key Cove

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

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (1)
"very nice house , with 4 Rooms , 1 of them in the 1st floor so very convenient to my mom . kitchen is awesome , new and good quality appliances we take the kids to the club , there is a lazy river and the sliders are fun . No additional charges . "
5003 Windermere Avenue

Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

The price is AED 496
AED 1,009 total
includes taxes & fees
3 Mar - 4 Mar
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

Spacious Resort Home w/ Pool - 11 Mi to Disney!

3.0 star property
8.6 out of 10, Excellent, (4)
"The house was perfect for my family of 14. It was beautiful, large and very spacious. The property manager was not resposnive but the owner wss excellent.There were a couple of minor issues, but absolutely nothing that affected our stay. I'd definitely stay there again and would recommend to everyone. "
Spacious Resort Home w/ Pool - 11 Mi to Disney!

Caribbean Dreamin

3.0 star property
10.0 out of 10, Exceptional, (1)
"This Caribbean Dreamin property is awesome! It is clean, spacious, and very well kept. Contrary to the contract, the house includes all the amenities for all bathrooms as well as dishwashing detergent. Nice touch! The community is very pretty and well kept. Shopping nearby. Unfortunately, we were here for a couple nights during Hurricane Milton so didn't go out at all. But being in a nice home away from home made a difference during the stressful time. I would highly recommend this...
Caribbean Dreamin
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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Other property types in Kissimmee

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (1618)
"Beautiful property and the one bedroom suite was very spacious and clean. Furnishings were all updated and felt like a new home. Great amenities and kitchen. Really enjoyed. "
The price is AED 306
AED 403 total
includes taxes & fees
16 Mar - 17 Mar
Vacation Village at Parkway

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1227)
"Ok"
Margaritaville Resort Orlando Cottages by Rentyl

Barefoot'n Resort Kissimmee Orlando

2.5 star property
8.8 out of 10, Excellent, (15)
"For the price, this was absolutely a happy surprise, Our room was immaculate and walking across the street to old town, where there are lots of restaurants and fun things to see and do, was great! "
The price is AED 357
AED 451 total
includes taxes & fees
2 Mar - 3 Mar
Barefoot'n Resort Kissimmee Orlando
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.

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between AED 496 and AED 496 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?
Select from multiple cottages in Kissimmee with a total average guest review rating of 9.3. 1702vp is a terrific place to rest and recharge between adventures. This 3.5-star cottage also offers a swimming pool and WiFi. Stunning Lakeview Townhome With Private Pool is another top option with visitors to the area. It has a 4-star rating and amenities including beach volleyball activities and a swimming pool.
How many cottages are there in Kissimmee?
Choose from 995 cottages in Kissimmee. No matter if you’re vacationing with the kids or organizing a weekend break with your buddies, Expedia will help you find the right place to escape the hustle and bustle.
Are there any 5-star cottages in Kissimmee?
Kissimmee does not have any 5-star cottages — but you and your besties can still spend your days here in style! Why not choose Stunning Lakeview Townhome With Private Pool? Located around 8 kilometers from the downtown area, this 4-star escape features a swimming pool and a living room. 4720shd Ultimate New 6 Bedroom Storey Lake Home is another terrific 4-star pick just 8 kilometers from the center of Kissimmee. It offers a laid-back vibe close to nature on top of amenities like spa facilities and a swimming pool.
Why book your cottage in Kissimmee with Expedia?
Expedia has some great cottages in Kissimmee, so start planning for a memorable stay on nature’s doorstep. If you have a certain budget, select how much you’re willing to spend and the star rating of your property. Or, make your way to the filters to search for cottages with a pool or a kitchen. We’ll help you find a suitable place whatever your getaway looks like.
How can I find cheap cottages in Kissimmee?
The easiest way to compare cheap cottages in Kissimmee is with Expedia’s user-friendly filter tool. Narrow your search by amenities, budget and star rating to grab excellent rates in just a few clicks.