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Cottage vacation rentals in Kissimmee

Find and book unique cottages on Airbnb

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Popular amenities for Kissimmee cottage rentals

Cottage rentals with a pool

Guest favorite
Cottage in Kissimmee
4.91 out of 5 average rating, 205 reviews

Cozy Private Cottage 5 miles from Disney!

KaitlynnRating, 5 stars2 weeks ago
Simple but very cute. It’s a great size for two people. Was able to fit two cars in the driveway with no issue. Will be returning. Quiet neighborhood
Guest favorite
Private room in Kissimmee
4.9 out of 5 average rating, 71 reviews

A Luxurious Haven near Disney! Tiny home

LexiRating, 5 stars1 week ago
Very very cozy and comfy getaway spot! Loved every minute we spent here. Our hosts were fantastic and so helpful and responsive. We definitely will be back
Cottage in Kissimmee
4.22 out of 5 average rating, 86 reviews

Gorgeous 4 bed/3 bath, Private Pool and Spa Home

TiffanyRating, 5 stars5 months ago
Very beautiful home very clean and lots of things to use for cooking I will definitely recommend her place and if I ever come back I would definitely stay at her place again
Cottage in Kissimmee
4.79 out of 5 average rating, 28 reviews

The Cozy Porch

BillRating, 5 stars1 week ago
Heydi's place was fantastic, perfectly located, quiet, comfortable, clean, and convenient. While only being minutes away from tons of things to do from parks, restaurants, and other experiences, once in this spot it was quiet calm and relaxing. Everything you could need from laundry, a peaceful enclosed porch and outdoor patio area along with some very nice amenities such as a pool, gym, library, and even hot tub, this spot is everything would need and want. Heydi took every proactive step to make things as easy as possible for guests from arrival to stay to checkout. This is an ideal gem for those wanting to enjoy the parks or be near the airport with minimal time wasted in traffic, perfectly situated near every where you'd want to be while still offering some peace and quiet before and after. Heydi made our stay so much more enjoyable thanks to her thoughtfulness and accommodating approach. Thank you for a wonderful stay
Cottage in Kissimmee
4.63 out of 5 average rating, 115 reviews

Charming lakeside hideaway! Near Disney

MatheusRating, 5 stars3 weeks ago
Perfect House! As for the photos, we felt at home! Thank you so much
Cottage in Kissimmee
4.89 out of 5 average rating, 19 reviews

Mickey&Minie Honey moon cottage house10 min.Disney

NaquieshaRating, 5 stars3 weeks ago
Enjoyed stay Quiet neighborhood
Guest favorite
Cottage in Kissimmee
4.86 out of 5 average rating, 7 reviews

Cozy Tiny Home Getaway minutes from Disney

MelindaRating, 5 stars2 months ago
Loved my stay! I typically stay at Disney when I come from Ohio, but took the chance on this beauty! Everything was as described, it was clean and every detail was thought of, including mini space heaters! Getting to and from the parks was super easy and parking was a dream. Thank you! I hope to be back!
Guest favorite
Cottage in Kissimmee
4.89 out of 5 average rating, 38 reviews

Sherwood - Disney Get'A'Way

KaitlynRating, 5 stars2 months ago
Great stay nice and clean has everything that you would need for a stay in the Disney area. And very safe area where the air bnb is located :)

Cottage rentals with a hot tub

Top guest favorite
Cottage in Kissimmee
5 out of 5 average rating, 14 reviews

Kiwi Cottage at Margaritaville Resort, near Disney

ClareRating, 5 stars1 month ago
My husband and I stayed for 2 weeks at this lovely cottage. It was clean and very comfortable with plenty of space. We loved using the private hot tub in the cool mornings and private pool in the afternoon. Hedging on the fences provided nice privacy. We only used our rental car once to make one run to target for s few groceries ( many beginning supplies were provided). Otherwise, we enjoyed walking to many restaurants. The owners were very communicative during the whole process. Very relaxing time.
Top guest favorite
Cottage in Kissimmee
4.99 out of 5 average rating, 74 reviews

Getaway Cottage Near Disney

YuhanRating, 5 stars1 week ago
We had a wonderful stay at Sue’s lovely cottage! The home was clean, cozy, beautiful, and had everything we needed for a comfortable visit. Sue provided very clear and detailed instructions, which made our arrival and stay so easy. The neighborhood felt safe and peaceful — a perfect spot to relax after spending time at the parks. We appreciated all the little touches in the home, and Sue was always responsive and kind whenever we had questions. We would love to stay again in the future.
Cottage in Kissimmee
4.74 out of 5 average rating, 150 reviews

Sherwood Forest Vacation Home Near Disney

CarolRating, 5 stars6 days ago
This is a great location to stay. close by all the attractions. it isconly about an hour away from the Kennedy Space Center and Cocoa Beach.
Cottage in Kissimmee
4.75 out of 5 average rating, 138 reviews

Hidden Lake View Cottage 4 miles from Disney!

CelesteRating, 5 stars1 week ago
This place was the perfect quiet spot to return to after a long day at Disney! It was cozy and quiet, and that back porch is spectacular!
Top guest favorite
Cottage in Kissimmee
4.98 out of 5 average rating, 176 reviews

2/2 Condo with Patio- Epic Universe, Magic Kingdom

GenevieveRating, 5 stars1 week ago
We really enjoyed our stay at this appartment. Melanie responded quickly to our messages and the place is perfect for a small family. We appreciated the proximity to a big Walmart (13 minutes walk). We also enjoyed the many pools available, the mini golf and the gym (24h). Nice little spot also to sit outside and enjoy the view. It is also very close to Disney sites (about 15 minutes), and we often used the free shuttle. We will certainly come back to this place when we return to Disney or Universal.
Guest favorite
Cottage in Kissimmee
4.8 out of 5 average rating, 80 reviews

Chic Cottage near Disney - Lots of Amenities!

MattRating, 5 stars1 week ago
Hernan’s home was cozy and the development was very peaceful. Any questions we had were quickly answered and Hernan made sure to do whatever he could to make the stay as enjoyable as possible! Development pools and clubhouses were clean and comfortable. We were traveling with our small child, and Hernan made sure that we had what we needed ahead of time. No complaints about noise or disruption from the neighbors. Very decent location, close to stores, theme parks and local attractions. Definitely bookmarking this one for future trips!
Guest favorite
Cottage in Kissimmee
4.89 out of 5 average rating, 45 reviews

Beautiful Cottage 2 Bedroom

JoRating, 5 stars1 month ago
Would recommend. Very cute park.
Cottage in Kissimmee
4.76 out of 5 average rating, 135 reviews

"Beautiful Resort Cottage Near All Attractions!!"

AliciaRating, 5 stars3 weeks ago
Giovanny was very responsive, respectful and responded quickly. The place was roomy for 3 of us, and it was peaceful. We enjoy the rest!! Thank you!

Pet-friendly cottage rentals

Superhost
Cottage in Four Corners
4.84 out of 5 average rating, 45 reviews

Amazing! 4BD Cottage in Margaritaville near Disney

CameronRating, 5 stars3 months ago
The unit was very clean and felt new. The photos accurately show what the place looks like. Host Daniel was friendly and very responsive, always answering my inquiries quickly and efficiently! Would stay there again for sure.
Guest favorite
Cottage in Kissimmee
4.94 out of 5 average rating, 65 reviews

Rare 2 Bed + Hot Tub nr Disney in Margaritaville

LucyRating, 5 stars1 month ago
Thank you Daniel once again for hosting our stay. We come down every 3 months for Scoliosis Treatment and it makes it so easy and relaxing after such a long day in Celebration Florida. love the cottages.
Guest favorite
Cottage in Kissimmee
5 out of 5 average rating, 69 reviews

2BD Cottage w/spa near Disney! in Margaritaville

MattRating, 5 stars2 weeks ago
Fantastic place. 2 king beds 2 bathrooms. Local to a lot of great restaurants and attractions. Outstanding communication from Daniel! Would recommend!
Top guest favorite
Cottage in Kissimmee
4.99 out of 5 average rating, 70 reviews

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

EricRating, 5 stars3 weeks ago
Daniel’s place is outstanding and looks just like the photos. We had a great stay and can’t wait to come back!
Guest favorite
Cottage in Kissimmee
5 out of 5 average rating, 38 reviews

Tropical 4BD Cottage in Margaritaville nr Disney!

ChrisRating, 5 stars2 weeks ago
We had a great stay! Quiet community. Great for the pups. The house had a lot of space and was very comfortable. Close proximity to the parks.
Guest favorite
Cottage in Kissimmee
5 out of 5 average rating, 12 reviews

2 Bed Hot Tub Cottage in Margaritaville Phase 1!

JorgeRating, 5 stars4 months ago
Place is beautiful and well located. Nearby you will find plenty of restaurants, grocery store, and entertainment. Place was clean and had all the amenities you need. Unfortunately we were not able to use the hot tub after a full day of walking through parks, as it seems it was not properly sanitized. We communicated with Daniel and he responded immediately. Aside from this hiccup, we had a pleasant stay. We would stay there again.
Cottage in Davenport
4.67 out of 5 average rating, 39 reviews

Free parking Full house lake view and king Bed

JasmynnRating, 5 stars1 week ago
The house was very clean and the beds were comfortable. The location was very quiet! Highly recommend will definitely be back!
Cottage in Orlando
4.73 out of 5 average rating, 107 reviews

Twigy's Cozy Studio in Downtown Orlando

JessicaRating, 5 stars4 days ago
Twigy, thank you for allowing me to experience your little piece of paradise. It was quiet and the location was just what I needed for the wknd. The back yard was so serene. I was visited by a black racer who was passing through but other than that, I enjoyed the privacy and peaceful surroundings. My stay over all was 10/10! Thank you again. I will definitely try to rebook when I’m in town.

Quick stats about cottage rentals in Kissimmee

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    2.8K reviews

  • Rentals with a pool

    10 properties have a pool

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee
  6. Cottage rentals