Guesthouse vacation rentals in Kissimmee
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Kissimmee
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Kissimmee guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Orlando
4.94 out of 5 average rating, 389 reviewsGarden House near Orlando's cultural hub
Guesthouse in Windermere
4.94 out of 5 average rating, 241 reviewsSmall Guesthouse near Orlando's Theme Parks
Guesthouse in Orlando
4.84 out of 5 average rating, 318 reviewsNice Brand New Studio !!
Guesthouse in Orlando
4.96 out of 5 average rating, 370 reviewsThe Coach House- 2 bedroom/3 bath Orlando Getaway!
Guesthouse in Orlando
4.96 out of 5 average rating, 82 reviewsBungalow Guesthouse Downtown Orlando
Guest house rentals with a patio
Guesthouse in Orlando
4.9 out of 5 average rating, 108 reviewsDowntown private pool house. Two blocks from ORMC
Guesthouse in Orlando
5.0 out of 5 average rating, 156 reviewsThe Sacred Space Downtown Orlando Milk District
Guesthouse in Orlando
4.94 out of 5 average rating, 140 reviewsHidden Luxury Gem w/ private porch
Guesthouse in Orlando
4.88 out of 5 average rating, 136 reviews“The Clementine” Quaint Boho Home in Local Orlando
Guesthouse in Winter Garden
4.94 out of 5 average rating, 53 reviewsBlue Heron Bungalow
Guesthouse in Orlando
4.92 out of 5 average rating, 38 reviewsCozy new guesthouse to yourself.
Guesthouse in Orlando
4.94 out of 5 average rating, 34 reviewsDowntown Cozy/Modern Studio
Guesthouse in Orlando
4.95 out of 5 average rating, 38 reviewsPalm Suite at Bliss House
Guest house rentals with a washer and dryer
Guesthouse in Orlando
4.84 out of 5 average rating, 201 reviewsLovely Spacious Guesthouse in Mills 50 District
Guesthouse in Orlando
4.9 out of 5 average rating, 384 reviewsBungalow Close to Attractions and Downtown Orlando
Guesthouse in Davenport
4.94 out of 5 average rating, 154 reviewsWinsome Farm Guest House
Guesthouse in Orlando
4.85 out of 5 average rating, 133 reviews☼BohoBungalow ☼ Close to EVERYTHING! Work frm home
Guesthouse in Orlando
4.99 out of 5 average rating, 240 reviewsBlack House- Private Cottage in Thornton Park!
Guesthouse in Kissimmee
4.9 out of 5 average rating, 92 reviewsCozy 1BR apt-Pool/Tennis/Gym/Near attractions
Guesthouse in Orlando
4.9 out of 5 average rating, 51 reviewsKyle's Place - No Cleaning Fee + Laundry Room
Guesthouse in Four Corners
4.93 out of 5 average rating, 15 reviewsBeachGuyDave's Reunion Guesthome
Quick stats about guesthouse rentals in Kissimmee
Total rentals
20 properties
Local attractions
Star Island Resort & Club, Silver Spurs Arena, and FantasyWorld Resort
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Total number of reviews
770 reviews
Nightly prices starting at
$30 before taxes and fees
Destinations to explore
- St Petersburg Vacation rentals
- Anna Maria Island Vacation rentals
- Sarasota Vacation rentals
- Tampa Vacation rentals
- Key West Vacation rentals
- Naples Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- West Palm Beach Vacation rentals
- Orlando Vacation rentals
- House rentals United States
- Guesthouse rentals United States
- House rentals Orlando
- Guesthouse rentals Orlando
- House rentals Kissimmee
- Cottage rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with a home theater Kissimmee
- Rentals with an EV charger Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Beachfront rentals Kissimmee
- Rentals with a fire pit Kissimmee
- Townhouse rentals Kissimmee
- Apartment rentals Kissimmee
- Family-friendly rentals Kissimmee
- Villa rentals Kissimmee
- Cabin rentals Kissimmee
- Rentals with breakfast Kissimmee
- Tiny house rentals Kissimmee
- Rentals with a sauna Kissimmee
- Waterfront rentals Kissimmee
- Rentals with a kayak Kissimmee
- Serviced apartment rentals Kissimmee
- Rentals with pools Kissimmee
- Rentals with a fireplace Kissimmee
- Rentals with beach access Kissimmee
- Rentals with outdoor seating Kissimmee
- Pet-friendly rentals Kissimmee
- Private suite rentals Kissimmee
- Monthly Rentals Kissimmee
- Rentals with a washer and dryer Kissimmee
- Rentals with an accessible height bed Kissimmee
- Condo rentals Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Kid-friendly rentals Kissimmee
- Hotel rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with lake access Kissimmee
- Wheelchair accessible rentals Kissimmee
- Guesthouse rentals Florida
- House rentals Florida
- Guesthouse rentals Florida
- House rentals Florida
- Guesthouse rentals Tampa
- House rentals Tampa
- House rentals Osceola County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes