Guesthouse holiday rentals in Orlando
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Top-rated Guesthouses in Orlando
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 Orlando guesthouses
Family-Friendly guesthouses
Guesthouse in Orlando
4.99 out of 5 average rating, 199 reviewsYour Home Away From Home
11–18 Jul
Guesthouse in Windermere
4.94 out of 5 average rating, 239 reviewsSmall Guesthouse near Orlando's Theme Parks
6–13 Jan
Guesthouse in Orlando
4.84 out of 5 average rating, 318 reviewsNice Brand New Studio !!
7–14 May
Guesthouse in Maitland
4.87 out of 5 average rating, 381 reviewsChez Bienvenu
23–30 Mar
Guesthouse in Winter Park
4.82 out of 5 average rating, 234 reviewsWELCOME HOME IN WINTER PARK
31 Oct – 7 Nov
Guesthouse in Orlando
4.94 out of 5 average rating, 388 reviewsGarden House near Orlando's cultural hub
5–12 Jun
Guesthouse in Clermont
4.85 out of 5 average rating, 149 reviewsDiscover Tranquility at Our Charming Guest House
19–26 Jun
Guesthouse in Orlando
4.96 out of 5 average rating, 366 reviewsThe Coach House- 2 bedroom/3 bath Orlando Getaway!
19–26 Mar
Guesthouses with a patio
Guesthouse in Maitland
4.98 out of 5 average rating, 116 reviewsPrivate 1-bd Mid-Century Guesthouse
11–18 Jan
Guesthouse in Orlando
4.88 out of 5 average rating, 131 reviews“The Clementine” Quaint Boho Home in Local Orlando
21–28 Feb
Guesthouse in Orlando
4.93 out of 5 average rating, 138 reviewsHidden Luxury Gem w/ private porch
25 May – 1 Jun
Guesthouse in Orlando
4.8 out of 5 average rating, 56 reviewsVintage Florida Vibes House
25 Oct – 1 Nov
Guesthouse in Orlando
4.94 out of 5 average rating, 54 reviewsThe Green Room Orlando
17–24 Sep
Guesthouse in Orlando
4.94 out of 5 average rating, 36 reviewsPalm Suite at Bliss House
7–14 Jan
Guesthouse in Orlando
4.91 out of 5 average rating, 57 reviewsThe Cottage
13–20 Nov
Guesthouse in Orlando
5.0 out of 5 average rating, 26 reviewsLocation, Location, Location!
17–24 Apr
Guest house rentals with a washing machine and dryer
Guesthouse in Orlando
4.97 out of 5 average rating, 286 reviewsOasis Garden Cottage -cozy, chic, near everything!
5–12 Aug
Guesthouse in Orlando
4.98 out of 5 average rating, 346 reviewsLakefront Seclusion modern guesthouse+Pool+Hot tub
30 Sep – 7 Oct
Guesthouse in Orlando
4.83 out of 5 average rating, 198 reviewsLovely Spacious Guesthouse in Mills 50 District
28 Jan – 4 Feb
Guesthouse in Orlando
4.91 out of 5 average rating, 144 reviews8th Green Cottage - A relaxing oasis in the city
8–15 Jul
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
4.98 out of 5 average rating, 105 reviewsLuxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF
23–30 Jul
Guesthouse in Davenport
4.93 out of 5 average rating, 150 reviewsWinsome Farm Guest House
30 Jan – 6 Feb
Quick stats about guesthouse rentals in Orlando
Total rentals
230 properties
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
18K reviews
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