Guesthouse vacation rentals in Kissimmee
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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
4.96 out of 5 average rating, 141 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, 136 reviewsβThe Clementineβ Quaint Boho Home in Local Orlando
Guesthouse in Orlando
4.94 out of 5 average rating, 35 reviewsDowntown Cozy/Modern Studio
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, 39 reviewsCozy new guesthouse to yourself.
Guesthouse in Orlando
4.99 out of 5 average rating, 81 reviewsKing Bed π Fire Pit π₯ Private βοΈ Grill π Location
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
4.98 out of 5 average rating, 352 reviewsLakefront Seclusion modern guesthouse+Pool+Hot tub
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
4.99 out of 5 average rating, 240 reviewsBlack House- Private Cottage in Thornton Park!
Guesthouse in Orlando
4.85 out of 5 average rating, 134 reviewsβΌBohoBungalow βΌ Close to EVERYTHING! Work frm home
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
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