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
May 23 – 30
Guesthouse in Windermere
4.94 out of 5 average rating, 240 reviewsSmall Guesthouse near Orlando's Theme Parks
Mar 21 – 28
Guesthouse in Orlando
4.84 out of 5 average rating, 318 reviewsNice Brand New Studio !!
Sep 25 – Oct 2
Guesthouse in Orlando
4.96 out of 5 average rating, 370 reviewsThe Coach House- 2 bedroom/3 bath Orlando Getaway!
Mar 3 – 10
Guesthouse in Orlando
4.83 out of 5 average rating, 18 reviewsLakefront Guest House by downtown :Boat, Fishing…
May 13 – 20
Guesthouse in Orlando
4.96 out of 5 average rating, 82 reviewsBungalow Guesthouse Downtown Orlando
Jan 23 – 30
Guest house rentals with a patio
Guesthouse in Orlando
4.9 out of 5 average rating, 108 reviewsDowntown private pool house. Two blocks from ORMC
Jun 21 – 28
Guesthouse in Orlando
5.0 out of 5 average rating, 155 reviewsThe Sacred Space Downtown Orlando Milk District
Nov 12 – 19
Guesthouse in Orlando
4.96 out of 5 average rating, 138 reviewsStylish Private Guest Suite in Downtown Orlando
Jul 1 – 8
Guesthouse in Orlando
4.94 out of 5 average rating, 140 reviewsHidden Luxury Gem w/ private porch
Jun 10 – 17
Guesthouse in Orlando
4.88 out of 5 average rating, 133 reviews“The Clementine” Quaint Boho Home in Local Orlando
Oct 5 – 12
Guesthouse in Orlando
4.92 out of 5 average rating, 38 reviewsCozy new guesthouse to yourself.
Aug 17 – 24
Guesthouse in Orlando
4.94 out of 5 average rating, 34 reviewsDowntown Cozy/Modern Studio
Aug 3 – 10
Guesthouse in Winter Garden
4.94 out of 5 average rating, 53 reviewsBlue Heron Bungalow
Jul 14 – 21
Guest house rentals with a washer and dryer
Guesthouse in Orlando
4.9 out of 5 average rating, 383 reviewsBungalow Close to Attractions and Downtown Orlando
Mar 18 – 25
Guesthouse in Orlando
4.84 out of 5 average rating, 201 reviewsLovely Spacious Guesthouse in Mills 50 District
Dec 1 – 8
Guesthouse in Davenport
4.93 out of 5 average rating, 153 reviewsWinsome Farm Guest House
Jan 7 – 14
Guesthouse in Orlando
4.85 out of 5 average rating, 133 reviews☼BohoBungalow ☼ Close to EVERYTHING! Work frm home
Aug 1 – 8
Guesthouse in Orlando
4.99 out of 5 average rating, 240 reviewsBlack House- Private Cottage in Thornton Park!
Jun 29 – Jul 6
Guesthouse in Kissimmee
4.9 out of 5 average rating, 91 reviewsCozy 1BR apt-Pool/Tennis/Gym/Near attractions
Sep 14 – 21
Guesthouse in Orlando
4.9 out of 5 average rating, 50 reviewsKyle's Place - No Cleaning Fee + Laundry Room
Apr 17 – 24
Guesthouse in Orlando
4.95 out of 5 average rating, 59 reviewsTiny house downtown orlando
May 15 – 22
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