Guesthouse holiday rentals in Winter Park
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in Winter Park
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 Winter Park guesthouses
Family-Friendly guesthouses
Guesthouse in Orlando
4.94 out of 5 average rating, 388 reviewsGarden House near Orlando's cultural hub
5–12 Jun
Guesthouse in Orlando
4.96 out of 5 average rating, 366 reviewsThe Coach House- 2 bedroom/3 bath Orlando Getaway!
31 Dec – 7 Jan
Guesthouse in Mount Dora
4.9 out of 5 average rating, 705 reviewsKey West cottage of Mt Dora
13–20 Jul
Guesthouse in Windermere
4.94 out of 5 average rating, 239 reviewsSmall Guesthouse near Orlando's Theme Parks
21–28 Mar
Guesthouse in Mount Dora
4.88 out of 5 average rating, 313 reviewsA Lakeshore Cottage vintage 1926
17–24 Jul
Guesthouse in Orlando
4.99 out of 5 average rating, 199 reviewsYour Home Away From Home
11–18 Jul
Guesthouse in Sanford
4.95 out of 5 average rating, 329 reviewsBungalow Steps to Downtown Sanford and Lake Monroe
28 Jun – 5 Jul
Guesthouse in Orlando
4.84 out of 5 average rating, 318 reviewsNice Brand New Studio !!
5–12 Sep
Guesthouses with a patio
Guesthouse in Orlando
4.88 out of 5 average rating, 218 reviewsCouples Oasis *Heated Pool* and Lake View
22–29 Aug
Guesthouse in Orlando
4.91 out of 5 average rating, 106 reviewsDowntown private pool house. Two blocks from ORMC
17–24 Jul
Guesthouse in Orlando
4.95 out of 5 average rating, 133 reviewsStylish Private Guest Suite in Downtown Orlando
13–20 Jun
Guesthouse in Orlando
4.88 out of 5 average rating, 131 reviews“The Clementine” Quaint Boho Home in Local Orlando
3–10 Apr
Guesthouse in Orlando
4.96 out of 5 average rating, 185 reviewsCharming 1 bedroom Casita with private entrance
19–26 Jul
Guesthouse in Orlando
4.93 out of 5 average rating, 138 reviewsHidden Luxury Gem w/ private porch
7–14 Jun
Guesthouse in Mount Dora
4.93 out of 5 average rating, 136 reviewsEnjoy downtown: modern studio w/ kitchenette
14–19 Aug
Guesthouse in Longwood
5.0 out of 5 average rating, 66 reviews"Winnie's Place" A Peaceful Guesthouse with Pool.
15–22 Dec
Guest house rentals with a washing machine and dryer
Guesthouse in Orlando
4.97 out of 5 average rating, 251 reviewsPeculiar newly built one bedroom Studio.
21–28 Sep
Guesthouse in Orlando
4.98 out of 5 average rating, 350 reviewsLakefront Seclusion modern guesthouse+Pool+Hot tub
17–24 Sep
Guesthouse in Orlando
4.9 out of 5 average rating, 381 reviewsBungalow Close to Attractions and Downtown Orlando
30 Mar – 6 Apr
Guesthouse in Orlando
4.98 out of 5 average rating, 105 reviewsLuxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF
30 Jun – 7 Jul
Guesthouse in Sanford
4.95 out of 5 average rating, 226 reviewsPalmetto Pool Retreat
27 Feb – 6 Mar
Guesthouse in Orlando
4.94 out of 5 average rating, 212 reviewsModern Guest Studio (Private) Pool / Spa available
26 Dec – 2 Jan
Guesthouse in Orlando
4.99 out of 5 average rating, 239 reviewsBlack House- Private Cottage in Thornton Park!
29 Jun – 6 Jul
Guesthouse in Mount Dora
4.97 out of 5 average rating, 167 reviewsThe Carriage House - Walk to Downtown!!!!
3–10 Oct
Quick stats about guesthouse rentals in Winter Park
Total rentals
30 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
30 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
2.6K reviews
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