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Tiny house holiday rentals in Kissimmee

Find and book unique tiny house rentals on Airbnb

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Popular amenities for Kissimmee tiny house rentals

Family-friendly tiny house rentals

Bungalow in Kissimmee
4.77 out of 5 average rating, 113 reviews

Sandcastle Cottage#51 Tropical Palms Kissimmee, FL

VirginiaRating, 5 stars3 months ago
Great Location, House is perfect for 2 people. Clean and had everything we needed. Host is very pro-active in making sure you have no trouble getting in to the Resort and House. Will be back
Guest favourite
Guesthouse in Winter Park
4.81 out of 5 average rating, 255 reviews

WELCOME HOME IN WINTER PARK

GreggRating, 5 stars2 weeks ago
I had a great stay at Muriel's place. The spot is only a block off the water, which provides great backdrops for walks. It's a private spot that's conveniently located (not walkable, but only a 5-minute drive) near to the park neighborhoods (Thornton, Audubon, Winter Park, College Park), Mills 50, and downtown. The neighborhood is very quiet and safe with easy access to I-4 and 17-92. This is a great, clean, and well-maintained spot, with a great host, that is well worth the price.
Top Guest favourite
Guesthouse in Windermere
4.94 out of 5 average rating, 269 reviews

Paradise nook near Orlando's theme parks

SarahRating, 5 stars1 month ago
We loved our stay. Beautiful place, very quiet and private. Clear instructions, easy check-in, place was very clean and comfortable. Right down the road from Yellow Dog Eats which was fantastic. Thank you Noga!
Superhost
Tiny home in Orlando
4.74 out of 5 average rating, 450 reviews

The Cottage 6 Month Lakefront Tiny House Rentals

JamesRating, 5 stars1 month ago
WOW!! We was In Orlando for a cheer comp and needed to stay an extra night and I found this place. I really got it kinda as a joke on my kids, the joke was on me. This is a beautiful place. So much to do and see, and SO peaceful.The people that live in the community are very friendly. My kids loved it. It is so peaceful and relaxing. I will definitely be renting here again in the future to be able to enjoy all the things there are to do. It was me and my 3 kids there.
Guest favourite
Cottage in Kissimmee
4.94 out of 5 average rating, 471 reviews

Entire cottage for 5, close to Disney, Universal!

RaishRating, 5 stars1 week ago
Very peaceful and beautiful! Had an excellent trip. Will try to stay here every time I go to Orlando.
Guest favourite
Cottage in Kissimmee
4.86 out of 5 average rating, 462 reviews

Yay! Cool Tiny Home Near All the Parks (98)

HeidiRating, 5 stars2 days ago
Great little place for four people if two are a couple :). The bottles of water in the fridge and the treats in the kitchen were a wonderful little surprise, and they were greatly appreciated. The neighborhood amenities are a bonus!
Cottage in Kissimmee
4.73 out of 5 average rating, 292 reviews

Cute Sandcastle Cottage near Disney

JamieRating, 5 stars1 month ago
Great place in a quiet, beautiful community and in an outstanding location. Highly recommend!
Top Guest favourite
Guesthouse in Orlando
4.94 out of 5 average rating, 415 reviews

Garden House near Orlando's cultural hub

RyanRating, 5 stars2 days ago
Terry was a great host, and very responsive to messages. Very easy to check in and out of with very clear instructions. The place was clean and tidy, and very quiet. It was a great place to stay! It's also very close to everything downtown!

Tiny house rentals with a patio

Top Guest favourite
Tiny home in Kissimmee
5 out of 5 average rating, 36 reviews

Private Tiny Home @ Disney Parks

JacquelineRating, 5 stars3 days ago
The house is super cute and clean perfect for a couple to stay in for a week! The pool was very nice. Joe is very responsive if you need anything and he left snacks! The description of the property was spot-on, as well as a very close to restaurants and shopping. Definitely recommend!
Guest favourite
Tiny home in Kissimmee
4.86 out of 5 average rating, 137 reviews

Surfer Mickey's Tiny House !

TamarahRating, 5 stars4 months ago
The house and amenities were just as described. They even left us some welcome snacks! The owner was easy to communicate with and responsive to any needs and questions
Guest favourite
Tiny home in Kissimmee
4.9 out of 5 average rating, 63 reviews

Private Tiny Home for Your Vaca!

MarelyRating, 5 stars2 weeks ago
Terre’s place was terrific ! It’s the perfect little house for a solo traveler or with small children as well . My 3 year old and I went and had fun by the pool & play area . Terre also left a mini snack bar with popcorn , cookies & bottles of water in the fridge . The place is perfect for even just relaxing in the front porch and it’s walking distance to a Mexican restaurant called “CALACAS”. I would definitely return to Terre’s place ! I couldn’t ask for more .
Top Guest favourite
Tiny home in Orlando
4.98 out of 5 average rating, 218 reviews

“La Casita” Tiny home with private yard

VirginiaRating, 5 stars2 days ago
Staying at this tiny house has been an absolute delight. From the moment we arrived, it truly felt like a home away from home. Every detail has been thoughtfully designed and carefully selected — from the cozy furniture and tasteful decor to the well-chosen appliances that make the space not only beautiful but also incredibly functional. You can tell a lot of heart went into creating this space. The layout makes the most of every inch, offering comfort without ever feeling cramped. One of the sweetest touches was the complimentary snacks such a kind and thoughtful gesture that made us feel especially welcome. We’ll be sure to recommend and hope to return to!
Guest favourite
Tiny home in Kissimmee
4.95 out of 5 average rating, 37 reviews

Tiny Treasure

JonnyRating, 5 stars3 weeks ago
Debra’s house was perfect fit for what we needed! We were only twenty five minutes from Orange County Convention Center, but right outside of Sea World and just south of Universal Studios and many other attractions! I really liked pulling into the private road, from the main street. We noticed all the fun things to do around the house; swimming, miniature golf, tennis, & very peaceful while going for morning walks. Waking up every morning was such a beautiful site to see from the front porch! The house was very clean and felt very comfortable. I will say for a Tiny House, it didn’t feel that way inside; amazing job! There are tons of restaurants and much needed stores within walking distance, or if you prefer driving it’s only within a mile or two! Jase and I had a fabulous time, we expect to be back for next year’s Collect-A-Con, or perhaps sooner to enjoy an amusement park or two! Thank you again Debra and hope to see you again💕
Guest favourite
Cottage in Kissimmee
4.8 out of 5 average rating, 87 reviews

Chic Cottage near Disney - Lots of Amenities!

Emma-GraceRating, 5 stars2 weeks ago
We stayed at Hernans place for a weekend and it was great for what we needed it for. To give an honest review I must say, upon entering it is important to note that this is very clearly an older building so some things are a little worn, no problem! We had a housekeeping issue and contacted Hernan and within 3 hours, the housekeeping team came and corrected all issues for us. Truly such an accommodating and kind host. We weren’t in the house much but when we were there we felt safe and comfortable. One thing I will note, there were 3 of us staying for a weekend with 1 roll of toilet paper. That was the only thing I forgot to mention to the host but I am sure if I did mention it, he would have corrected it. Great stay, great host!
Top Guest favourite
Tiny home in Kissimmee
5 out of 5 average rating, 22 reviews

Cozy Tiny Home Near Disney & Universal

EdnaleeRating, 5 stars3 weeks ago
Let me start by saying, all other AirBnB’s will have to step their game up! Robyn truly went above and beyond to make our time in her home as special as can be. Her communication was great, providing details for all things necessary and inquired. The space is even better in person! It has everything you will need and some for a weekend or more. The neighborhood is super cute and very close to restaurants, shopping, and attractions. My family and I did not want to leave! We really did feel right at home. We cannot wait to come back, and hopefully for longer. Thank you SO much Robyn. May God bless you and your home 🫶🏽
Top Guest favourite
Tiny home in Kissimmee
4.93 out of 5 average rating, 41 reviews

Butterfly Creek, serenity & joy of nature's beauty

MegRating, 5 stars1 month ago
Amazing property, amazing host, amazing stay! Nancy was so thoughtful and communicative. Had everything I needed and more. Tons of things to do in the area and this was the perfect place to wind down in the evening and wake up to in the mornings. Highly recommend staying on this property. Location was spot on, close enough to everything but felt very private and calming. Looking forward to coming back in the future.

Tiny house rentals with outdoor seating

Guest favourite
Guesthouse in Orlando
5 out of 5 average rating, 11 reviews

Lakeside Palm Escape

VerenaRating, 5 starstoday
5 sterren! Perfecte balans tussen rust en pretparkplezier 🌴🎢 Ons tweede verblijf hier in Orlando en opnieuw echt fantastisch! Op amper 20 à 30 minuten van de drukte van de pretparken, maar zodra je “thuis” komt, zit je meteen middenin de rust aan het meer. Zalig wakker worden met uitzicht op het water en genieten van de stilte — pure ontspanning. De woning is supermooi ingericht en heel goed onderhouden. Het zwembad is heerlijk en biedt verfrissing na een lange dag in de parken. Alles wat je nodig hebt is aanwezig, van keuken tot comfortabele bedden. We zouden deze plek zó opnieuw boeken. Echt een pareltje als je het beste wil van beide werelden: avontuur én rust!
Superhost
Tiny home in Davenport
4.65 out of 5 average rating, 17 reviews

Cozy Tiny Home with Bbq & Terrace near Disney Park

LindaRating, 5 stars2 months ago
Leticia’s place was cute and cozy. The outdoor spaces were perfect for our morning coffee and to sit and soak in some sun or unwind at night. We loved the little touches and snacks! Exactly what we needed for a short stay in Davenport!
Guest favourite
Tiny home in Kissimmee
4.86 out of 5 average rating, 21 reviews

Charming gem with lake views near Airport & Disney

KristopherRating, 5 stars1 week ago
Super cool. Fun theme. Easy in and out. Simple
Top Guest favourite
Tiny home in Davenport
4.96 out of 5 average rating, 49 reviews

Tiny home dream house with private entrance

BlaiseRating, 5 stars2 months ago
I really enjoyed my stay here! Super cozy and clean. Has everything you need during your stay, and Vane was extremely helpful with check in and answering all my questions
Tiny home in Kissimmee
4.75 out of 5 average rating, 24 reviews

No Cleaning Fee- Jedi cottage 4 miles to Disney

Maria CeciliaRating, 5 stars3 months ago
El apartamento es tal cual las fotos y descripción! Muy cómodo, limpio y en un barrio tranquilo y lindo! La casa tenía todo lo necesario para nuestra comodidad. Kathryn fue siempre muy amable en la comunicación. Realmente nos sentimos como en nuestra casa, volveríamos a hospedarnos allí, sin dudas!
Guest favourite
Tiny home in Kissimmee
4.84 out of 5 average rating, 45 reviews

Cottage near Disney World

LidianeRating, 5 stars1 month ago
A experiência foi ótima! Megan sempre prestativa e atenciosa, nos ofereceu todas as informações que precisávamos, sempre nos respondeu prontamente e foi solicita ao nos oferecer late check-out. A casa é organizada e bem equipada, exatamente como nas fotos. A localização é excelente, próxima aos parques e centros de compra, bem segura também! O único ponto de atenção é que a casa pode receber até 4 hóspedes, somos uma família de 4 adultos e a casa ficou muito apertada para nós, o sofá cama não é nem um pouco confortável e toma todo o espaço da sala, além disso, por ser trabalhoso de abrir, acabamos deixando a cama montada durante toda a estadia o que limitava ainda mais nosso espaço. Acredito que a experiência indo com apenas 2 pessoas seria muito melhor. Por fim, reforço que o custo benefício é ótimo, o atendimento é impecável e a casa, apesar de pequena, é muito charmosa e exatamente como nas fotos! Recomendo muito a hospedagem com a Megan ;)
Top Guest favourite
Tiny home in Kissimmee
4.97 out of 5 average rating, 68 reviews

!A Young Fun Tiny Home @ Disney!

StevenRating, 5 stars3 weeks ago
Jennifer was always quick to respond to messages and was super friendly and caring. She is a great host! The listing was extremely clean and a great place to stay for our family. We were definitely lucky to book this gem and will stay again in the future. We had an amazing stay! Thank you Jennifer!
Guest favourite
Tiny home in Kissimmee
4.9 out of 5 average rating, 279 reviews

Tiny House Fun - Near Parks and Airport!!

JonathanRating, 5 stars3 weeks ago
Great place to stay. I’ll be coming back soon for sure. 🤌🏻

Quick stats about tiny house rentals in Kissimmee

  • Total rentals

    40 properties

  • Nightly prices starting at

    $77 AUD before taxes and fees

  • Total number of reviews

    3K reviews

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 properties include access to Wi-Fi

Destinations to explore

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