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
4.94 out of 5 average rating, 388 reviewsGarden House near Orlando's cultural hub
Jun 5 – 12
Guesthouse in Leesburg
4.98 out of 5 average rating, 333 reviewsSilver Lake Guest Pool House
Oct 16 – 23
Guesthouse in Mount Dora
4.9 out of 5 average rating, 707 reviewsKey West cottage of Mt Dora
Oct 22 – 29
Guesthouse in Windermere
4.94 out of 5 average rating, 240 reviewsSmall Guesthouse near Orlando's Theme Parks
Aug 15 – 22
Guesthouse in Mount Dora
4.88 out of 5 average rating, 313 reviewsA Lakeshore Cottage vintage 1926
Jul 21 – 28
Guesthouse in Sanford
4.95 out of 5 average rating, 330 reviewsBungalow Steps to Downtown Sanford and Lake Monroe
Jan 19 – 26
Guesthouse in Orlando
4.84 out of 5 average rating, 318 reviewsNice Brand New Studio !!
May 8 – 15
Guesthouse in Clermont
4.85 out of 5 average rating, 149 reviewsDiscover Tranquility at Our Charming Guest House
Jun 24 – Jul 1
Guest house rentals with a patio
Guesthouse in Orlando
4.88 out of 5 average rating, 219 reviewsCouples Oasis *Heated Pool* and Lake View
Aug 21 – 28
Guesthouse in Orlando
4.88 out of 5 average rating, 133 reviews“The Clementine” Quaint Boho Home in Local Orlando
Jan 11 – 18
Guesthouse in Orlando
4.9 out of 5 average rating, 107 reviewsDowntown private pool house. Two blocks from ORMC
Jul 18 – 25
Guesthouse in Orlando
4.96 out of 5 average rating, 136 reviewsStylish Private Guest Suite in Downtown Orlando
Jun 25 – Jul 2
Guesthouse in Orlando
4.96 out of 5 average rating, 185 reviewsCharming 1 bedroom Casita with private entrance
Jan 3 – 10
Guesthouse in Orlando
4.94 out of 5 average rating, 139 reviewsHidden Luxury Gem w/ private porch
Jul 17 – 24
Guesthouse in Mount Dora
4.93 out of 5 average rating, 136 reviewsEnjoy downtown: modern studio w/ kitchenette
Aug 14 – 19
Guesthouse in Lake Eola Heights Historic District
4.95 out of 5 average rating, 40 reviewsAdorable 1-bedroom minutes from downtown Orlando
May 2 – 9
Guest house rentals with a washer and dryer
Guesthouse in Orlando
4.96 out of 5 average rating, 252 reviewsPeculiar One bedroom Studio.
Nov 29 – Dec 6
Guesthouse in Orlando
4.9 out of 5 average rating, 382 reviewsBungalow Close to Attractions and Downtown Orlando
Dec 31 – Jan 7
Guesthouse in Orlando
4.93 out of 5 average rating, 227 reviewsBungalow Near Downtown Orlando - No Cleaning Fee!
Jul 5 – 12
Guesthouse in Sanford
4.95 out of 5 average rating, 227 reviewsPalmetto Pool Retreat
Nov 11 – 18
Guesthouse in Orlando
4.98 out of 5 average rating, 106 reviewsLuxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF
Feb 8 – 15
Guesthouse in Orlando
4.99 out of 5 average rating, 240 reviewsBlack House- Private Cottage in Thornton Park!
Jun 29 – Jul 6
Guesthouse in Mount Dora
4.97 out of 5 average rating, 168 reviewsThe Carriage House - Walk to Downtown!!!!
Jan 16 – 23
Guesthouse in Orlando
4.94 out of 5 average rating, 213 reviewsModern Guest Studio (Private) Pool / Spa available
Jul 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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