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Featured Cottages in Kissimmee and around

Large Villa W/private Pool & Game Room! Waterpark

3.5 star property
9.6 out of 10, Exceptional, (10)
"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 "
The price is €658
includes taxes & fees
23 Feb - 24 Feb
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

10.0 out of 10, Exceptional, (4)
"It was a short but fun birthday weekend.I had asked for an early check in from the start and then ask to ask again on Friday and denied.Basically when we where getting in a couple left next to us and we had no neighbors."
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 . "
The price is €610
includes taxes & fees
25 Feb - 26 Feb
5003 Windermere Avenue

Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

The price is €268
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, (1531)
"Several pool and hot tub options. Nice area for walking. Family friendly. Shuttle around the village and to grocery store. Friendly staff While it is generally peaceful, we could hear moving of furniture and other sounds from the unit above us. "
The price is €113
includes taxes & fees
23 Mar - 24 Mar
Vacation Village at Parkway

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1209)
"Everything appeared to be new and clean. The cottages were near all the attractions and the staff was efficient and friendly. "
Margaritaville Resort Orlando Cottages by Rentyl

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1689)
"Easy checking in"
The price is €117
includes taxes & fees
3 Mar - 4 Mar
Barefoot Suites
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?
Cottages in Kissimmee range between €658 and €658 per night. These properties offer a chance to soak up nature’s beauty — at a price you can afford. 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?
Kissimmee has multiple cottages with a total average guest review rating of 9.3. 1702vp is a great option if you’re a fan of nature and an easygoing pace. Guests of this 3.5-star stay can enjoy amenities such as a swimming pool and WiFi. Stunning Lakeview Townhome With Private Pool is another popular pick. This 4-star cottage comes with beach volleyball activities and a swimming pool.
How many cottages are there in Kissimmee?
Claim your holiday time and pick from 995 cottages in Kissimmee. Imagining a place where you can get in touch with nature? Expedia can help you find your ideal getaway in a few quick clicks.
Are there any family-friendly cottages in Kissimmee?
A trip with your group in Kissimmee is simple at Stunning Lakeview Townhome With Private Pool. With amenities including a playground and a lazy river, you’ll find all the necessary comforts at this 4-star cottage. 4720shd Ultimate New 6 Bedroom Storey Lake Home is another family-friendly property where you and the rest of your crew can take time out from the hectic pace of big city life. This cottage has a 4-star rating and amenities including clothes washing facilities and WiFi. Once you’ve checked in and unpacked your suitcase, there’s no shortage of family-friendly attractions to see around Kissimmee. Kissimmee Golf Club and 192 Flea Market guarantee fun for young and old.
Are there any 5-star cottages in Kissimmee?
You won’t find any 5-star cottages in Kissimmee. But you will find some fabulous 4-star stays that are bound to make an impression. Reserve your spot at Stunning Lakeview Townhome With Private Pool, around 8 kilometres from downtown. a swimming pool and an ice maker are just a couple of the amenities available here. 4720shd Ultimate New 6 Bedroom Storey Lake Home is another upmarket option with spa facilities and a swimming pool. This cosy cottage is around 8 kilometres from central Kissimmee.
Why book your cottage in Kissimmee with Expedia?
Reserving a cottage in Kissimmee is as easy as clicking on your travel dates and choosing an ideal place for a holiday in nature. From luxurious retreats to low-cost stays and cottages that come with conveniences like a kitchen, Expedia has something for all tastes and styles. As for the best deals around? We’ve got you covered!
How can I find cheap cottages in Kissimmee?
With Expedia’s helpful filter tool, locating cheap cottages in Kissimmee couldn’t be simpler. To view properties that’ll make your bank balance smile, narrow your search by amenities, star rating and budget.
What is there to do in Kissimmee near my cottage?
There are plenty of fabulous things that’ll fill up your itinerary in Kissimmee. You won’t want to miss big attractions like Fun Spot America, Medieval Times and Capone’s Dinner Show. Skate Reflections, AMF Bowling Centre and Wizardz Magic Theatre are also visitor favourites.