Guest house holiday rentals in Kissimmee
Find and book unique guest house rentals on Airbnb
Top-rated guest house rentals in Kissimmee
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for guest house rentals in Kissimmee
Family-friendly guest house rentals
Guest house in Mount Dora
4.9 out of 5 average rating, 708 reviewsKey West cottage of Mt Dora
4–11 Oct
Guest house in Orlando
4.93 out of 5 average rating, 162 reviewsPrivate Backyard Cottage in Mills50
20–27 Oct
Guest house in Mount Dora
4.88 out of 5 average rating, 313 reviewsA Lakeshore Cottage vintage 1926
17–24 Nov
Guest house in Orlando
4.84 out of 5 average rating, 318 reviewsNice Brand New Studio !!
16–23 Aug
Guest house in Lakeland
4.98 out of 5 average rating, 214 reviewsModern lakeside retreat by SEU and FSC
10–17 Jun
Guest house in Winter Park
4.82 out of 5 average rating, 234 reviewsWELCOME HOME IN WINTER PARK
22–29 Oct
Guest house in Windermere
4.94 out of 5 average rating, 240 reviewsSmall Guesthouse near Orlando's Theme Parks
25 Jun – 2 Jul
Guest house in Maitland
4.87 out of 5 average rating, 381 reviewsChez Bienvenu
29 Aug – 5 Sep
Guest house rentals with a patio
Guest house in Winter Haven
4.84 out of 5 average rating, 147 reviewsAdorable 1 bedroom Guesthouse near Lego Land
31 Jul – 7 Aug
Guest house in Orlando
4.96 out of 5 average rating, 186 reviewsCharming 1 bedroom Casita with private entrance
6–13 Jan
Guest house in Orlando
4.95 out of 5 average rating, 133 reviewsJefferson St. Cottage
26 Nov – 3 Dec
Guest house in Orlando
5.0 out of 5 average rating, 155 reviewsThe Sacred Space Downtown Orlando Milk District
28 Jan – 4 Feb
Guest house in Maitland
4.98 out of 5 average rating, 118 reviewsPrivate 1-bd Mid-Century Guesthouse
10–17 Oct
Guest house in Mount Dora
4.93 out of 5 average rating, 136 reviewsEnjoy downtown: modern studio w/ kitchenette
23–28 Jun
Guest house in Orlando
4.88 out of 5 average rating, 133 reviews“The Clementine” Quaint Boho Home in Local Orlando
4–11 Apr
Guest house in Lakeland
4.95 out of 5 average rating, 105 reviewsHidden Emerald-Apartment with Kitchen and Laundry
20–27 Mar
Guest house rentals with a washing machine and dryer
Guest house in Davenport
4.93 out of 5 average rating, 153 reviewsWinsome Farm Guest House
4–11 Oct
Guest house in Orlando
4.85 out of 5 average rating, 133 reviews☼BohoBungalow ☼ Close to EVERYTHING! Work frm home
15–22 Dec
Guest house in Orlando
4.9 out of 5 average rating, 50 reviewsKyle's Place - No Cleaning Fee + Laundry Room
10–17 Apr
Guest house in Davenport
4.87 out of 5 average rating, 39 reviewsCozy Getaway Studio APT near Disney & Attractions
17–24 Oct
Guest house in Kissimmee
4.9 out of 5 average rating, 91 reviewsCozy 1BR apt-Pool/Tennis/Gym/Near attractions
4–11 Jul
Guest house in Four Corners
4.93 out of 5 average rating, 15 reviewsBeachGuyDave's Reunion Guesthome
6–13 Apr
Guest house in Orlando
4.97 out of 5 average rating, 67 reviewsThe Cottage (Pets stay for free)
8–15 Sep
Guest house in Orlando
5.0 out of 5 average rating, 21 reviewsModern Private Studio
24 Jun – 1 Jul
Destinations to explore
- St Petersburg Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Boca Raton Holiday rentals
- West Palm Beach Holiday rentals
- Orlando Holiday rentals
- House rentals United States
- Guest house rentals United States
- House rentals Orlando
- Guest house rentals Orlando
- Waterfront rentals Kissimmee
- Rentals with a kayak Kissimmee
- Villa rentals Kissimmee
- Rentals with breakfast Kissimmee
- Beachfront rentals Kissimmee
- Monthly Rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Cabin rentals Kissimmee
- Rentals with an EV charger Kissimmee
- Rentals with pools Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Apartment rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Rentals with beach access Kissimmee
- Cottage rentals Kissimmee
- Wheelchair-accessible rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Family-friendly rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Rentals with a cinema Kissimmee
- House rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Private suite rentals Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Flat rentals Kissimmee
- Rentals with a sauna Kissimmee
- Tiny house rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Rentals with lake access Kissimmee
- Rentals with outdoor seating Kissimmee
- Hotel rentals Kissimmee
- House rentals Florida
- Guest house rentals Florida
- House rentals Florida
- Guest house rentals Florida
- Guest house rentals Tampa
- House rentals Tampa
- House rentals Osceola County
- 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