Guesthouse holiday rentals in Kissimmee
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Top-rated Guesthouses in Kissimmee
Guests agree: These guesthouses 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 Kissimmee guesthouses
Family-Friendly guesthouses
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, 240 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
4.83 out of 5 average rating, 18 reviewsLakefront Guest House by downtown :Boat, Fishing…
Guesthouse in Orlando
4.96 out of 5 average rating, 82 reviewsBungalow Guesthouse Downtown Orlando
Guesthouses 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, 155 reviewsThe Sacred Space Downtown Orlando Milk District
Guesthouse in Orlando
4.96 out of 5 average rating, 139 reviewsStylish Private Guest Suite in Downtown Orlando
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, 135 reviews“The Clementine” Quaint Boho Home in Local Orlando
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 Winter Garden
4.94 out of 5 average rating, 53 reviewsBlue Heron Bungalow
Guest house rentals with a washing machine and dryer
Guesthouse in Orlando
4.9 out of 5 average rating, 383 reviewsBungalow Close to Attractions and Downtown Orlando
Guesthouse in Orlando
4.84 out of 5 average rating, 201 reviewsLovely Spacious Guesthouse in Mills 50 District
Guesthouse in Davenport
4.93 out of 5 average rating, 153 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, 91 reviewsCozy 1BR apt-Pool/Tennis/Gym/Near attractions
Guesthouse in Orlando
4.9 out of 5 average rating, 50 reviewsKyle's Place - No Cleaning Fee + Laundry Room
Guesthouse in Orlando
4.95 out of 5 average rating, 60 reviewsTiny house downtown orlando
Destinations to explore
- St Petersburg Holiday rentals
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- Rentals with a kayak Kissimmee
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