Guesthouse vacation rentals in Winter Park
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Winter Park
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 Winter Park guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Sanford
4.95 out of 5 average rating, 330 reviewsBungalow Steps to Downtown Sanford and Lake Monroe
Nov 24 – Dec 1
Guesthouse in Orlando
4.84 out of 5 average rating, 318 reviewsNice Brand New Studio !!
Aug 16 – 23
Guesthouse in Orlando
4.94 out of 5 average rating, 389 reviewsGarden House near Orlando's cultural hub
May 23 – 30
Guesthouse in Mount Dora
4.88 out of 5 average rating, 313 reviewsA Lakeshore Cottage vintage 1926
Nov 21 – 28
Guesthouse in Windermere
4.94 out of 5 average rating, 240 reviewsSmall Guesthouse near Orlando's Theme Parks
Jun 25 – Jul 2
Guesthouse in Mount Dora
4.9 out of 5 average rating, 708 reviewsKey West cottage of Mt Dora
Oct 4 – 11
Guesthouse in Clermont
4.85 out of 5 average rating, 149 reviewsDiscover Tranquility at Our Charming Guest House
Jun 28 – Jul 5
Guesthouse in Orlando
4.83 out of 5 average rating, 18 reviewsLakefront Guest House by downtown :Boat, Fishing…
May 13 – 20
Guest house rentals with a patio
Guesthouse in Orlando
4.88 out of 5 average rating, 220 reviewsCouples Oasis *Heated Pool* and Lake View
Aug 18 – 25
Guesthouse in Orlando
4.88 out of 5 average rating, 133 reviews“The Clementine” Quaint Boho Home in Local Orlando
Apr 4 – 11
Guesthouse in Orlando
4.9 out of 5 average rating, 107 reviewsDowntown private pool house. Two blocks from ORMC
Jul 27 – Aug 3
Guesthouse in Orlando
4.96 out of 5 average rating, 186 reviewsCharming 1 bedroom Casita with private entrance
Jan 6 – 13
Guesthouse in Orlando
4.94 out of 5 average rating, 140 reviewsHidden Luxury Gem w/ private porch
Jun 26 – Jul 3
Guesthouse in Orlando
4.96 out of 5 average rating, 137 reviewsStylish Private Guest Suite in Downtown Orlando
Sep 5 – 12
Guesthouse in Mount Dora
4.93 out of 5 average rating, 136 reviewsEnjoy downtown: modern studio w/ kitchenette
Jun 23 – 28
Guesthouse in Orlando
5.0 out of 5 average rating, 27 reviewsLocation, Location, Location!
Nov 26 – Dec 3
Guest house rentals with a washer and dryer
Guesthouse in Orlando
4.98 out of 5 average rating, 351 reviewsLakefront Seclusion modern guesthouse+Pool+Hot tub
Apr 12 – 19
Guesthouse in Orlando
4.96 out of 5 average rating, 252 reviewsPeculiar One bedroom Studio.
Dec 11 – 18
Guesthouse in Orlando
4.9 out of 5 average rating, 383 reviewsBungalow Close to Attractions and Downtown Orlando
Mar 6 – 13
Guesthouse in Orlando
4.98 out of 5 average rating, 106 reviewsLuxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF
Sep 27 – Oct 4
Guesthouse in Sanford
4.95 out of 5 average rating, 227 reviewsPalmetto Pool Retreat
Nov 20 – 27
Guesthouse in Orlando
4.94 out of 5 average rating, 213 reviewsModern Guest Studio (Private) Pool / Spa available
Jul 28 – Aug 4
Guesthouse in Orlando
4.93 out of 5 average rating, 227 reviewsBungalow Near Downtown Orlando - No Cleaning Fee!
Oct 24 – 31
Guesthouse in Orlando
4.99 out of 5 average rating, 240 reviewsBlack House- Private Cottage in Thornton Park!
May 19 – 26
Quick stats about guesthouse rentals in Winter Park
Total rentals
30 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
30 properties include access to wifi
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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