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 Mount Dora
4.9 out of 5 average rating, 708 reviewsKey West cottage of Mt Dora
Oct 4 – 11
Guesthouse in Orlando
4.93 out of 5 average rating, 162 reviewsPrivate Backyard Cottage in Mills50
Oct 20 – 27
Guesthouse in Mount Dora
4.88 out of 5 average rating, 313 reviewsA Lakeshore Cottage vintage 1926
Nov 17 – 24
Guesthouse in Orlando
4.84 out of 5 average rating, 318 reviewsNice Brand New Studio !!
Aug 16 – 23
Guesthouse in Lakeland
4.98 out of 5 average rating, 214 reviewsModern lakeside retreat by SEU and FSC
Jun 10 – 17
Guesthouse in Winter Park
4.82 out of 5 average rating, 234 reviewsWELCOME HOME IN WINTER PARK
Oct 22 – 29
Guesthouse in Windermere
4.94 out of 5 average rating, 240 reviewsSmall Guesthouse near Orlando's Theme Parks
Jun 25 – Jul 2
Guesthouse in Maitland
4.87 out of 5 average rating, 381 reviewsChez Bienvenu
Aug 29 – Sep 5
Guest house rentals with a patio
Guesthouse in Winter Haven
4.84 out of 5 average rating, 147 reviewsAdorable 1 bedroom Guesthouse near Lego Land
Jul 31 – Aug 7
Guesthouse in Orlando
4.96 out of 5 average rating, 186 reviewsCharming 1 bedroom Casita with private entrance
Jan 6 – 13
Guesthouse in Orlando
4.95 out of 5 average rating, 133 reviewsJefferson St. Cottage
Nov 26 – Dec 3
Guesthouse in Orlando
5.0 out of 5 average rating, 155 reviewsThe Sacred Space Downtown Orlando Milk District
Jan 28 – Feb 4
Guesthouse in Maitland
4.98 out of 5 average rating, 118 reviewsPrivate 1-bd Mid-Century Guesthouse
Oct 10 – 17
Guesthouse in Mount Dora
4.93 out of 5 average rating, 136 reviewsEnjoy downtown: modern studio w/ kitchenette
Jun 23 – 28
Guesthouse in Orlando
4.88 out of 5 average rating, 133 reviews“The Clementine” Quaint Boho Home in Local Orlando
Apr 4 – 11
Guesthouse in Lakeland
4.95 out of 5 average rating, 105 reviewsHidden Emerald-Apartment with Kitchen and Laundry
Mar 20 – 27
Guest house rentals with a washer and dryer
Guesthouse in Davenport
4.93 out of 5 average rating, 153 reviewsWinsome Farm Guest House
Oct 4 – 11
Guesthouse in Orlando
4.85 out of 5 average rating, 133 reviews☼BohoBungalow ☼ Close to EVERYTHING! Work frm home
Dec 15 – 22
Guesthouse in Orlando
4.9 out of 5 average rating, 50 reviewsKyle's Place - No Cleaning Fee + Laundry Room
Apr 10 – 17
Guesthouse in Davenport
4.87 out of 5 average rating, 39 reviewsCozy Getaway Studio APT near Disney & Attractions
Oct 17 – 24
Guesthouse in Kissimmee
4.9 out of 5 average rating, 91 reviewsCozy 1BR apt-Pool/Tennis/Gym/Near attractions
Jul 4 – 11
Guesthouse in Four Corners
4.93 out of 5 average rating, 15 reviewsBeachGuyDave's Reunion Guesthome
Apr 6 – 13
Guesthouse in Orlando
4.97 out of 5 average rating, 67 reviewsThe Cottage (Pets stay for free)
Sep 8 – 15
Guesthouse in Orlando
5.0 out of 5 average rating, 20 reviewsModern Private Studio
Jun 24 – Jul 1
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
- Guesthouse rentals United States
- House rentals United States
- Guesthouse rentals Orlando
- House rentals Orlando
- Hotel rentals Kissimmee
- Monthly Rentals Kissimmee
- Rentals with a washer and dryer Kissimmee
- Private suite rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Family-friendly rentals Kissimmee
- Kid-friendly rentals Kissimmee
- Rentals with breakfast Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Rentals with a fire pit Kissimmee
- Fitness-friendly rentals Kissimmee
- Tiny house rentals Kissimmee
- Villa rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Cabin rentals Kissimmee
- Rentals with lake access Kissimmee
- Rentals with a kayak Kissimmee
- Rentals with a patio Kissimmee
- Rentals with an EV charger Kissimmee
- Townhouse rentals Kissimmee
- Rentals with beach access Kissimmee
- Rentals with a home theater Kissimmee
- Rentals with a sauna Kissimmee
- Beachfront rentals Kissimmee
- Condo rentals Kissimmee
- Smoking-friendly rentals Kissimmee
- Wheelchair accessible rentals Kissimmee
- Rentals with an accessible height bed Kissimmee
- Cottage rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Rentals with pools Kissimmee
- Rentals with outdoor seating Kissimmee
- Waterfront rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Apartment rentals Kissimmee
- House rentals Kissimmee
- Guesthouse rentals Florida
- House rentals Florida
- Guesthouse rentals Florida
- House rentals Florida
- House rentals Tampa
- Guesthouse 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