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Check prices for these dates

Next weekend
Mar 21 - Mar 23
In two weeks
Mar 28 - Mar 30
In one month
Apr 11 - Apr 13
In two months
May 9 - May 11

Featured Cottages in Kissimmee

8081 Knee Deep Rd
Miscellaneous

8081 Knee Deep Rd

3.0 star property
10.0 out of 10, Exceptional, (1)
"Nuestra experiencia fue muy buena las condiciones son perfectas el único detalle que no me gustó fue el baño de arriba que cuando te bañas se llena la bañadera de agua está tupida lo demás perfecto y tiene todo lo que puedes necesitar "
8081 Knee Deep Rd
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
Pool

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

3.0 star property
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
8000 Lost Shaker Lane
Miscellaneous

8000 Lost Shaker Lane

3.0 star property
9.8 out of 10, Exceptional, (6)
"Beautiful and clean! Easy to find, great location, easy check in and out and very roomy space! Everything you need is provided! Comfortable beds! Only thing I’d change is find an easier way to contact host with questions, such as direct texting. Otherwise, it’s call them, leave a message and wait for a call back. Or send a message through their chat and days to get a response. That said everything I needed - check in/check out proceedings was sent on time through email . Overall, a great...
8000 Lost Shaker Lane
Large Villa W/private Pool & Game Room! Waterpark
Miscellaneous

Large Villa W/private Pool & Game Room! Waterpark

3.5 star property
9.6 out of 10, Exceptional, (11)
"Large family , wonderful beds !! Nice big house tons of bathrooms, would stay again 4 sure "
Large Villa W/private Pool & Game Room! Waterpark
3-br Condo BBQ & Heated Pool Near Disney&malls
Outdoor pool

3-br Condo BBQ & Heated Pool Near Disney&malls

3.0 star property
3-br Condo BBQ & Heated Pool Near Disney&malls
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Outdoor pool

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
Pool

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
Margarita Porch Paradise
View from room

Margarita Porch Paradise

5.0 star property
10.0 out of 10, Exceptional, (2)
"The house was beautiful and comfortable for our family, we would have stayed longer! The resort is fun, plenty of stores and good restaurants. We will definitely come back. "
Margarita Porch Paradise
Stunning Lakeview Townhome w/ Private Pool!
Outdoor pool

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.4 out of 10, Very Good, (10)
"Perfect location house was just what is described "
Stunning Lakeview Townhome w/ Private Pool!
Modern Townhome W/private Pool & Free Water Park!
Miscellaneous

Modern Townhome W/private Pool & Free Water Park!

4.0 star property
8.8 out of 10, Excellent, (5)
"This property was excellent and lived up to the expectations in the post! So close to the parks, we came back everyday to cool down by the pool and recharge our batteries."
Modern Townhome W/private Pool & Free Water Park!
3000 Latitude Lane
Interior

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
3-br Condo Family Retreat Near Disney Gym&pool
Miscellaneous

3-br Condo Family Retreat Near Disney Gym&pool

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was really nice and spacious. The team does great at communication. We arrived hours before check in and for just a small fee they let us check in early. The houses are well cleaned! I would forsure stay again and recommend this for anyone!"
3-br Condo Family Retreat Near Disney Gym&pool
Spacious Vacation Rental w/ Yard in Kissimmee!
Interior

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!
5003 Windermere Avenue
Miscellaneous

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
8462 Secret Key Cove
Miscellaneous

8462 Secret Key Cove

3.0 star property
8.0 out of 10, Very Good, (1)
8462 Secret Key Cove
Caribbean Dreamin
3 bedrooms, free WiFi, bed sheets

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
Enchanting House few min Away From the Parks 52
Outdoor pool

Enchanting House few min Away From the Parks 52

3.0 star property
Enchanting House few min Away From the Parks 52
Spacious Resort Home w/ Pool - 11 Mi to Disney!
Outdoor pool

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!
3148 Caribbean Soul Drive
Interior

3148 Caribbean Soul Drive

3.0 star property
3148 Caribbean Soul Drive
Luxury Villa, South Facing Pool! No Rear Neighbors. Themed Rooms, Theatre & Game Room. #8so8956
Outdoor pool

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
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
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (1712)
"So. Nice. "
The price is P4,786
P6,293 total
includes taxes & fees
Apr 1 - Apr 2
Vacation Village at Parkway
Margaritaville Resort Orlando Cottages by Rentyl
Interior

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1247)
"Beautiful resort. Everyone was very nice. Checkin process a little slow. Our room had used towels from previous guests- were behind door so didn’t notice until our friends came and used the bathroom. Had concerns about how clean that bathroom was if they didn’t take out used towels."
Margaritaville Resort Orlando Cottages by Rentyl
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.2 out of 10, Wonderful, (25)
"Beautiful place for a holiday my only recommendation to mgmt is to hear pool. The pool is cold. "
The price is P5,574
P7,043 total
includes taxes & fees
Mar 12 - Mar 13
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 and 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 733 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 family-friendly cottages in Kissimmee?
Put your feet up at Stunning Lakeview Townhome With Private Pool, a 4-star cottage not far from town. Conveniences here include a waterslide and a playground. Another family-friendly pick where you can swap the urban jungle for fresh air and nature is 4720shd Ultimate New 6 Bedroom Storey Lake Home. Clothes washing facilities and WiFi help make this 4-star cottage a hit with guests. Kissimmee boasts plenty of family-friendly attractions to discover when you need to keep the kids busy. Kissimmee Golf Club and 192 Flea Market guarantee a fun day out for both young and old.
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.
What is there to do in Kissimmee near my cottage?
Whatever you love to do, Kissimmee has tons of things to capture your imagination. 192 Flea Market, Osceola Square Mall and Lake Cecile are on many travelers’ to-do lists. Don’t leave without exploring Kissimmee Golf Club, Old Town and Silver Spurs Arena either. With Expedia’s hotel deals in Kissimmee, you can discover even more neat attractions like these with the money you save.