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 Windermere
4.94 out of 5 average rating, 239 reviewsSmall Guesthouse near Orlando's Theme Parks
21–28 Mar
Guesthouse in Orlando
4.84 out of 5 average rating, 318 reviewsNice Brand New Studio !!
5–12 Sep
Guesthouse in Orlando
4.83 out of 5 average rating, 18 reviewsLakefront Guest House by downtown :Boat, Fishing…
8–15 May
Guesthouse in Kissimmee
4.92 out of 5 average rating, 51 reviewsBird Watchers Delight - home close to Disney WIFI
3–10 Aug
Guesthouse in Orlando
4.96 out of 5 average rating, 82 reviewsBungalow Guesthouse Downtown Orlando
2–9 Nov
Guesthouses with a patio
Guesthouse in Orlando
4.93 out of 5 average rating, 138 reviewsHidden Luxury Gem w/ private porch
7–14 Jun
Guesthouse in Orlando
4.8 out of 5 average rating, 56 reviewsVintage Florida Vibes House
9–16 Oct
Guesthouse in Orlando
4.92 out of 5 average rating, 59 reviewsThe Cottage
17–24 Nov
Guesthouse in Orlando
4.92 out of 5 average rating, 37 reviewsCozy new guesthouse to yourself.
13–20 Jan
Guesthouse in Orlando
4.95 out of 5 average rating, 37 reviewsPalm Suite at Bliss House
7–14 Jan
Guesthouse in Orlando
4.99 out of 5 average rating, 79 reviewsKing Bed 👑 Fire Pit 🔥 Private ⭐️ Grill 🍗 Location
6–13 Sep
Guesthouse in Orlando
4.95 out of 5 average rating, 60 reviewsGlamorous guesthouse City Center! 10 min Downtown
21–28 Jun
Guesthouse in Orlando
4.97 out of 5 average rating, 32 reviewsDowntown Cozy/Modern Studio
21–28 Feb
Guest house rentals with a washing machine and dryer
Guesthouse in Orlando
4.9 out of 5 average rating, 381 reviewsBungalow Close to Attractions and Downtown Orlando
8–15 Mar
Guesthouse in Orlando
4.98 out of 5 average rating, 350 reviewsLakefront Seclusion modern guesthouse+Pool+Hot tub
17–24 Sep
Guesthouse in Davenport
4.93 out of 5 average rating, 151 reviewsWinsome Farm Guest House
30 Jan – 6 Feb
Guesthouse in Orlando
4.99 out of 5 average rating, 239 reviewsBlack House- Private Cottage in Thornton Park!
29 Jun – 6 Jul
Guesthouse in Orlando
4.85 out of 5 average rating, 132 reviews☼BohoBungalow ☼ Close to EVERYTHING! Work frm home
17–24 Nov
Guesthouse in Orlando
4.9 out of 5 average rating, 48 reviewsKyle's Place - No Cleaning Fee + Laundry Room
11–18 Dec
Guesthouse in Orlando
5.0 out of 5 average rating, 18 reviewsModern Private Studio
17–24 Jul
Guesthouse in Four Corners
4.93 out of 5 average rating, 14 reviewsBeachGuyDave's Reunion Guesthome
1–8 Apr
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, Wi-Fi and Pool
Wi-Fi availability
20 properties include access to Wi-Fi
Total number of reviews
770 reviews
Nightly prices starting at
$50 NZD before taxes and fees
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