Skip to content

Guesthouse vacation rentals in Kissimmee

Find and book unique guesthouse rentals on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.

Top-rated guesthouse rentals in Kissimmee

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Orlando
Couples Oasis Heated Pool and Lake View
Have a romantic getaway in this SODO Couples Oasis Retreat with private pool or come work alone in this peaceful oasis. Perfect for couples or the busy profesional who want privacy and quiet with lake view while relaxing in the patio chairs by the pool. Centrally located in SODO by downtown Orlando. Close to everything. Walk to great nearby eating places. Love ice cream Kelly’s Hand Made ice cream is a 5 minute walk from the house.
Apr 15 – 22
$111 per night
4.87 out of 5 average rating, 202 reviews
Guest favorite
Guesthouse in Orlando
Lakefront Seclusion modern guesthouse+Pool+Hot tub
An oasis in the city is what you will be surprised to find here at your guest house, located on a peaceful estate on the shore of Lake Hourglass. Secluded from the noises of the city, but still just minutes from everything, it's the perfect base to explore Orlando from, or perhaps to enjoy a staycation at if you're a local! For check out, please just enjoy your stay with us, you don’t need do any tidy or clean steps for us.
Dec 25 – Jan 1
$189 per night
4.96 out of 5 average rating, 339 reviews
Guest favorite
Guesthouse in Four Corners
Quiet Room Close to Disney and Attractions
Quaint and quiet retreat just minutes from attractions. Private in-law suite and bathroom, detached from main house. Features all the basic amenities of a hotel room with the feeling of home. Room is perfect for up to three persons. Queen bed and additional sleeper sofa. Located in Reunion Resort. There is a pool, gym, and spa located within the resort but not on the property and is for Reunion club members only.
Dec 14 – 21
$81 per night
4.98 out of 5 average rating, 416 reviews

Popular amenities for Kissimmee guesthouse rentals

Family-friendly guest house rentals

Superhost
Guesthouse in Dade City
Studio Zen
May 5 – 12
$58 per night
4.82 out of 5 average rating, 211 reviews
Superhost
Guesthouse in Clermont
Discover Tranquility at Our Charming Guest House
Jun 17 – 24
$200 per night
4.85 out of 5 average rating, 144 reviews
Guest favorite
Guesthouse in Orlando
Garden House near Orlando's cultural hub
Apr 5 – 12
$92 per night
4.94 out of 5 average rating, 382 reviews
Guest favorite
Guesthouse in Winter Park
WELCOME HOME IN WINTER PARK
Dec 8 – 15
$89 per night
4.81 out of 5 average rating, 227 reviews
Guest favorite
Guesthouse in Orlando
Nice Brand New Studio !!
Mar 24 – 31
$70 per night
4.84 out of 5 average rating, 313 reviews
Guest favorite
Guesthouse in Windermere
Small Guesthouse near Orlando's Theme Parks
Aug 30 – Sep 6
$117 per night
4.94 out of 5 average rating, 233 reviews
Superhost
Guesthouse in Orlando
Lakefront Guest House by downtown :Boat, Fishing…
Mar 14 – 21
$132 per night
4.82 out of 5 average rating, 17 reviews
Guest favorite
Guesthouse in Kissimmee
Bird Watchers Delight - home close to Disney WIFI
Jul 25 – Aug 1
$71 per night
4.92 out of 5 average rating, 51 reviews
Guesthouse in Orlando
Bungalow Guesthouse Downtown Orlando
Oct 30 – Nov 6
$210 per night
4.96 out of 5 average rating, 82 reviews

Guest house rentals with a patio

Guest favorite
Guesthouse in Orlando
Charming 1 bedroom Casita with private entrance
Oct 29 – Nov 5
$51 per night
4.96 out of 5 average rating, 164 reviews
Guest favorite
Guesthouse in Orlando
Stylish Private Studio in Downtown Orlando
May 6 – 13
$107 per night
4.96 out of 5 average rating, 113 reviews
Guest favorite
Guesthouse in Orlando
The Sacred Space Downtown Orlando Milk District
Jan 30 – Feb 6
$107 per night
5.0 out of 5 average rating, 144 reviews
Guest favorite
Guesthouse in Orlando
Hidden Luxury Gem w/ private porch
Apr 8 – 15
$85 per night
4.92 out of 5 average rating, 115 reviews
Guest favorite
Guesthouse in Orlando
“The Clementine” Quaint Boho Home in Local Orlando
Feb 14 – 21
$97 per night
4.87 out of 5 average rating, 110 reviews
Guest favorite
Guesthouse in Kissimmee
Kissimmee Studio
May 6 – 13
$40 per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Guesthouse in Orlando
Guesthouse hosted by Yadier
May 18 – 25
$108 per night
5.0 out of 5 average rating, 32 reviews
Guest favorite
Guesthouse in Orlando
Cozy studio Disney/Universal
Aug 20 – 27
$86 per night
4.9 out of 5 average rating, 41 reviews
Guest favorite
Guesthouse in Orlando
Downtown private pool house. Two blocks from ORMC
Apr 19 – 26
$71 per night
4.93 out of 5 average rating, 97 reviews
Superhost
Guesthouse in Lakeland
Countryside, tiny guesthouse, self checkin anytime
Jun 4 – 11
$63 per night
4.71 out of 5 average rating, 14 reviews
Guest favorite
Guesthouse in Orlando
Palm Suite at Bliss House
Oct 20 – 27
$133 per night
4.95 out of 5 average rating, 22 reviews
Guest favorite
Guesthouse in Orlando
Cozy new guesthouse to yourself.
Jun 3 – 10
$63 per night
4.94 out of 5 average rating, 32 reviews

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Orlando
Peculiar newly built one bedroom Studio.
Jul 10 – 17
$60 per night
4.97 out of 5 average rating, 240 reviews
Guest favorite
Guesthouse in Orlando
Lovely Spacious Guesthouse in Mills 50 District
Dec 29 – Jan 5
$63 per night
4.83 out of 5 average rating, 185 reviews
Guest favorite
Guesthouse in Orlando
Private Luxurious Apt. - Historic Downtown Orlando
Apr 26 – May 3
$129 per night
4.96 out of 5 average rating, 474 reviews
Guest favorite
Guesthouse in Orlando
Bungalow Close to Attractions and Downtown Orlando
Dec 8 – 15
$83 per night
4.89 out of 5 average rating, 368 reviews
Guest favorite
Guesthouse in Orlando
Oasis Garden Cottage -cozy, chic, near everything!
Aug 3 – 10
$96 per night
4.97 out of 5 average rating, 277 reviews
Guest favorite
Guesthouse in Orlando
Bungalow Central to Downtown ORL and Winter Park🦩
Apr 28 – May 5
$138 per night
4.92 out of 5 average rating, 225 reviews
Guest favorite
Guesthouse in Orlando
Black House- Private Cottage in Thornton Park!
Jul 6 – 13
$166 per night
4.99 out of 5 average rating, 236 reviews
Guest favorite
Guesthouse in Orlando
8th Green Cottage - A relaxing oasis in the city
Jul 21 – 28
$117 per night
4.9 out of 5 average rating, 136 reviews
Superhost
Guesthouse in Orlando
Cozy Guest Home 1.8 Miles from City Center
Apr 17 – 24
$84 per night
4.9 out of 5 average rating, 273 reviews
Guest favorite
Guesthouse in Orlando
Kyle's Place - No Cleaning Fee + Laundry Room
Oct 11 – 18
$73 per night
4.86 out of 5 average rating, 36 reviews
Guest favorite
Guesthouse in Kissimmee
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Apr 1 – 8
$129 per night
4.89 out of 5 average rating, 81 reviews
Superhost
Guesthouse in Orlando
Modern Private Studio
Apr 15 – 22
$88 per night
5.0 out of 5 average rating, 4 reviews

Quick stats about guesthouse rentals in Kissimmee

Total rentals

30 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

30 properties include access to wifi

Rentals with a pool

10 properties have a pool

Total number of reviews

720 reviews

Nightly prices starting at

$30 before taxes and fees

Destinations to explore

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