A pathway through a park with Spanish moss hanging from trees and a body of water in the background.

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Kissimmee cottages

A residential area with houses featuring sloped roofs and solar panels.

1. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is CA $115
CA $363 total
includes taxes & fees
Sep 29 - Sep 30
Upstay: Bright Family-friendly Retreat With Patio
A covered outdoor area with a concrete floor, surrounded by grass and trees.

2. Enchanted Cottage with Pool and Mini-Golf Near Disney

Enchanted Cottage with Pool and Mini-Golf Near Disney
Kissimmee
9.4 out of 10, Exceptional, (42 reviews)
"This place was the perfect little hideaway during our trip to the parks. Would most definitely stay again."
United States
Shane B.
The price is CA $111
CA $248 total
includes taxes & fees
Sep 17 - Sep 18
Enchanted Cottage with Pool and Mini-Golf Near Disney
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a black microwave.

3. Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (9 reviews)
"Proximity to theme parks, restaurants, and shopping"
United States
NOLI
The price is CA $93
CA $235 total
includes taxes & fees
Sep 14 - Sep 15
Tiny house close to Disney KISSIMMEE
A single-story mobile home with a front porch and a small deck.

4. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is CA $117
CA $291 total
includes taxes & fees
Sep 11 - Sep 12
Newly Remodeled Tiny Home 20 minutes from Disney!~
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

5. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is CA $112
CA $267 total
includes taxes & fees
Sep 12 - Sep 13
Perfect Place for a Perfect Vacation
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

6. Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is CA $130
CA $424 total
includes taxes & fees
Sep 13 - Sep 14
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A building with a central arched entrance, surrounded by a landscaped garden with palm trees and shrubs.

7. Pond Access & Grill! Group Escape, 19 Mi to WDW

Pond Access & Grill! Group Escape, 19 Mi to WDW
3.0 star property
Kissimmee
The price is CA $203
CA $473 total
includes taxes & fees
Sep 11 - Sep 12
Pond Access & Grill! Group Escape, 19 Mi to WDW
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

8. Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Kissimmee
The price is CA $128
CA $305 total
includes taxes & fees
Sep 22 - Sep 23
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A modern living room with a sofa, a large wall clock, and a mirror.

9. Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is CA $124
CA $282 total
includes taxes & fees
Sep 22 - Sep 23
Family-Friendly Cottage Near Orlando’s Top Attractions
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

10. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is CA $220
CA $1,152 total
includes taxes & fees
Sep 20 - Sep 21
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

11. Bella Vida House With Pool and Games - Near Disney!

Bella Vida House With Pool and Games - Near Disney!
3.0 star property
Bellavida
The price is CA $191
CA $654 total
includes taxes & fees
Sep 13 - Sep 14
Bella Vida House With Pool and Games - Near Disney!
A restaurant with outdoor seating and a thatched roof.

12. "Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (13 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is CA $123
CA $366 total
includes taxes & fees
Sep 13 - Sep 14
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
A modern hotel with a central courtyard, palm trees, and a parking area.

13. Mvy7664 - 3BR House Near Disney With Hot Tub

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
Mvy7664 - 3BR House Near Disney With Hot Tub
A single-story house with a brick facade, a garage, and a well-maintained lawn.

14. ~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
The price is CA $198
CA $656 total
includes taxes & fees
Sep 11 - Sep 12
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
A small, single-story house with a gray roof and white siding, featuring two white plastic chairs outside.

15. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (195 reviews)
"The cabins were great loved it there"
United States
Jennifer
The price is CA $94
CA $105 total
includes taxes & fees
Sep 11 - Sep 12
Lake Ida Beach Resort
A house with a red door, a front porch, and a pathway leading to the entrance.

16. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is CA $88
CA $243 total
includes taxes & fees
Sep 16 - Sep 17
Downtown Cottage
A residential property with a red carpet leading to a door, a small garden area with green turf and potted plants, and a wooden fence.

17. Garden Retreat in St. Cloud with WiFi, AC.

Garden Retreat in St. Cloud with WiFi, AC.
St. Cloud
10.0 out of 10, Exceptional, (32 reviews)
"Great cute and clean place."
United States
Victoria T.
The price is CA $131
CA $215 total
includes taxes & fees
Sep 13 - Sep 14
Garden Retreat in St. Cloud with WiFi, AC.
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

18. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is CA $154
CA $465 total
includes taxes & fees
Sep 30 - Oct 1
Family Resort Home w Pool, BBQ & Game Room
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

19. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is CA $98
CA $215 total
includes taxes & fees
Sep 11 - Sep 12
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A covered porch with rustic wooden chairs and a view of a road and water body.

20. Lakefront Retreat on Lake Ariana w/ EV Charger

Lakefront Retreat on Lake Ariana w/ EV Charger
3.0 star property
Auburndale
8.0 out of 10, Very good, (1 review)
"This house has beautiful views of Lake Ariana and you can walk to old town and access the lake easily. The house is an old classic central Florida house with some quirks, but had room for family and entertaining. Auburndale beautiful and was a great place to visit and had quick access to highways. "
United States
Katrina
The price is CA $159
CA $461 total
includes taxes & fees
Sep 13 - Sep 14
Lakefront Retreat on Lake Ariana w/ EV Charger
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

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"Clean"
Luis 1-night trip
Posted 6 hours ago
Vacation Village Orlando, Celebration

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
295
Accommodation
1480 Cottages
Lowest Price
CA $105
Highest Price
CA $1,152

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between CA $105 and CA $1,152 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?
Pick from multiple cottages in Kissimmee with a total average guest review rating of 9.1. 1702vp is a great place to relax and recharge between adventures. This 3.5-star cottage also features a swimming pool and WiFi. 4720shd Ultimate New 6 Bedroom Storey Lake Home is another leading pick with visitors to this area. It has a 4-star rating and amenities including a swimming pool and clothes washing facilities.
How many cottages are there in Kissimmee?
Choose from 1480 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?
Get cozy at 4720shd Ultimate New 6 Bedroom Storey Lake Home, a 4-star cottage not far from town. Amenities here include WiFi and clothes washing facilities. Another family-friendly pick where you can swap the concrete jungle for wide open spaces is Stunning Lakeview Townhome With Private Pool. A playground and a lazy river help make this 4-star cottage a traveller favourite. Once you've checked in and dropped off your luggage, there are lots of family-friendly attractions to see in and around Kissimmee. Discovery Cove and Aquatica guarantee fun for young and old.
Are there any 5-star cottages in Kissimmee?
Kissimmee does not have any 5-star cottages — but you and your crew can still vacation here in style! Why not choose 4720shd Ultimate New 6 Bedroom Storey Lake Home? Located around 8 kilometres from the downtown area, this 4-star retreat features beauty services and a swimming pool. Stunning Lakeview Townhome With Private Pool is another excellent 4-star choice just 8 kilometres from the centre of Kissimmee. It provides a relaxed vibe close to nature on top of amenities like a swimming pool and a lanai.
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.

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