Guesthouse vacation rentals in Winter Park
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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 Orlando
4.97 out of 5 average rating, 372 reviewsThe Coach House- 2 bedroom/3 bath Orlando Getaway!
Guesthouse in Leesburg
4.98 out of 5 average rating, 337 reviewsSilver Lake Guest Pool House
Guesthouse in Windermere
4.94 out of 5 average rating, 242 reviewsSmall Guesthouse near Orlando's Theme Parks
Guesthouse in Mount Dora
4.9 out of 5 average rating, 718 reviewsKey West cottage of Mt Dora
Guesthouse in Sanford
4.95 out of 5 average rating, 332 reviewsBungalow Steps to Downtown Sanford and Lake Monroe
Guesthouse in Mount Dora
4.87 out of 5 average rating, 316 reviewsA Lakeshore Cottage vintage 1926
Guesthouse in Orlando
4.84 out of 5 average rating, 321 reviewsNice Brand New Studio !!
Guesthouse in Orlando
4.99 out of 5 average rating, 199 reviewsYour Home Away From Home
Guest house rentals with a patio
Guesthouse in Orlando
4.95 out of 5 average rating, 135 reviewsJefferson St. Cottage
Guesthouse in Orlando
4.96 out of 5 average rating, 150 reviews*Stylish* Private Guest Suite-Downtown Orlando
Guesthouse in Orlando
4.96 out of 5 average rating, 191 reviewsCharming 1 bedroom Casita with private entrance
Guesthouse in Orlando
4.88 out of 5 average rating, 143 reviews“The Clementine” Quaint Boho Home in Local Orlando
Guesthouse in Orlando
4.89 out of 5 average rating, 112 reviewsDowntown private pool house. Two blocks from ORMC
Guesthouse in Orlando
4.88 out of 5 average rating, 227 reviewsCouples Oasis *Heated Pool* and Lake View
Guesthouse in Orlando
4.94 out of 5 average rating, 142 reviewsHidden Luxury Gem w/ private porch
Guesthouse in Mount Dora
4.93 out of 5 average rating, 140 reviewsEnjoy downtown: modern studio w/ kitchenette
Guest house rentals with a washer and dryer
Guesthouse in Orlando
4.96 out of 5 average rating, 258 reviewsPeculiar One bedroom Studio.
Guesthouse in Orlando
4.93 out of 5 average rating, 229 reviewsBungalow Near Downtown Orlando - No Cleaning Fee!
Guesthouse in Sanford
4.95 out of 5 average rating, 232 reviewsPalmetto Pool Retreat
Guesthouse in Orlando
4.9 out of 5 average rating, 388 reviewsBungalow Close to Attractions and Downtown Orlando
Guesthouse in Orlando
4.94 out of 5 average rating, 217 reviewsModern Guest Studio (Private) Pool / Spa available
Guesthouse in Orlando
4.98 out of 5 average rating, 110 reviewsLuxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF
Guesthouse in Orlando
4.99 out of 5 average rating, 240 reviewsBlack House- Private Cottage in Thornton Park!
Guesthouse in Orlando
4.85 out of 5 average rating, 135 reviews☼BohoBungalow ☼ Close to EVERYTHING! Work frm home
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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