Search Kissimmee Cottage Rentals from CA $118

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Kissimmee cottages

Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (7 reviews)
"Nice, Cute little place"
United States
Brenda N.
The price is CA $95
CA $237 total
includes taxes & fees
May 25 - May 26
Tiny house close to Disney KISSIMMEE
House (3 Bedrooms) | Interior

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is CA $108
CA $355 total
includes taxes & fees
May 26 - May 27
Upstay: Bright Family-friendly Retreat With Patio
House (3 Bedrooms) | Interior

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is CA $113
CA $531 total
includes taxes & fees
May 26 - May 27
Serenity - Family & Pet Friendly, Amazing Location
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (10 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is CA $150
CA $401 total
includes taxes & fees
Jun 8 - Jun 9
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

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 $111
CA $266 total
includes taxes & fees
May 25 - May 26
Perfect Place for a Perfect Vacation
Smart TV, books

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)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
The price is CA $124
CA $282 total
includes taxes & fees
May 25 - May 26
Family-Friendly Cottage Near Orlando’s Top Attractions
Dining

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 $127
CA $301 total
includes taxes & fees
Jun 3 - Jun 4
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
House (4 Bedrooms) | Interior

~ 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 $159
CA $648 total
includes taxes & fees
Jun 7 - Jun 8
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior

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 $123
CA $419 total
includes taxes & fees
Jun 10 - Jun 11
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Exterior

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 $248
CA $1,181 total
includes taxes & fees
Jun 3 - Jun 4
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
House (5 Bedrooms) | Interior

Family-friendly Villa w Pool, Hot Tub & Games Room

Family-friendly Villa w Pool, Hot Tub & Games Room
3.0 star property
Kissimmee
The price is CA $418
CA $832 total
includes taxes & fees
May 28 - May 29
Family-friendly Villa w Pool, Hot Tub & Games Room
House (3 Bedrooms) | Interior

Oasis Near Disney w Golf View, Family&pet Friendly

Oasis Near Disney w Golf View, Family&pet Friendly
3.0 star property
Reunion
The price is CA $132
CA $513 total
includes taxes & fees
May 26 - May 27
Oasis Near Disney w Golf View, Family&pet Friendly
House (4 Bedrooms) | Interior

Upstay: Pet-friendly Family Home w Pool & Sundeck

Upstay: Pet-friendly Family Home w Pool & Sundeck
3.0 star property
Kissimmee
The price is CA $161
CA $477 total
includes taxes & fees
May 25 - May 26
Upstay: Pet-friendly Family Home w Pool & Sundeck
House (5 Bedrooms) | Interior

Upstay - Resort Home w Cinema, Pool & Lake View

Upstay - Resort Home w Cinema, Pool & Lake View
3.0 star property
Kissimmee
Upstay - Resort Home w Cinema, Pool & Lake View
Porch

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (193 reviews)
"Was probably once a great time place. Owner was nice. Night time neighborhood is a bit noisy guess it's just how people act now no respect for property."
United States
wade
The price is CA $105
CA $118 total
includes taxes & fees
May 29 - May 30
Lake Ida Beach Resort
Exterior

New cottage retreat in St. Cloud with WiFi, AC.

New cottage retreat in St. Cloud with WiFi, AC.
St. Cloud
10.0 out of 10, Exceptional, (30 reviews)
"Great cute and clean place."
United States
Victoria T.
The price is CA $109
CA $190 total
includes taxes & fees
May 26 - May 27
New cottage retreat in St. Cloud with WiFi, AC.
House (2 Bedrooms) | Interior

Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
3.0 star property
Rosemont
10.0 out of 10, Exceptional, (2 reviews)
"The house was well supplied with amenities, family friendly and it was very fun to use the pool and games. There’s a super Walmart and other shops close by."
United States
Jennifer
The price is CA $187
CA $721 total
includes taxes & fees
Jun 8 - Jun 9
Chic Orlando Family Getaway w/ Fenced Yard!
Interior

Downtown Cottage

Downtown Cottage
Colonialtown North
8.2 out of 10, Very good, (11 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is CA $105
CA $264 total
includes taxes & fees
Jun 2 - Jun 3
Downtown Cottage
Property grounds

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (22 reviews)
"Host was very accommodating and the cottage was perfect"
United States
Ashley P.
The price is CA $205
CA $429 total
includes taxes & fees
May 29 - May 30
Cozy Lake Front Cottage
Exterior

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
9.8 out of 10, Exceptional, (37 reviews)
"Lovely spot, in a quiet neighborhood. Clean and spotless, and stocked with amenities for breakfast and snacks. We'll be booking again next time we go down to visit family in Orlando."
United States
John
The price is CA $247
CA $492 total
includes taxes & fees
Jun 15 - Jun 16
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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

Parkway International Resort

Parkway International Resort

10/10 Excellent
"Son apartamentos muy cómodos y súper limpios lo recomiendo 100 %"
Juan 2-night trip
Posted 3 hours ago
Parkway International Resort

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
304
Accommodation
1372 Cottages
Lowest Price
CA $118
Highest Price
CA $1,181

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between CA $118 and CA $1,181 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 9.4. 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 1372 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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