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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
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Guesthouse in Orlando
4.84 out of 5 average rating, 323 reviewsNice Brand New Studio !!
![](https://a0.muscache.com/im/pictures/miso/Hosting-21068544/original/58e32a5b-1147-4d3c-b462-e574f78b64b4.jpeg?im_w=720)
Guesthouse in Orlando
4.99 out of 5 average rating, 199 reviewsYour Home Away From Home
![](https://a0.muscache.com/im/pictures/4bb123c6-95d2-48fd-9a6c-a1f87bd0a1e7.jpg?im_w=720)
Guesthouse in Mount Dora
4.87 out of 5 average rating, 317 reviewsA Lakeshore Cottage vintage 1926
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Guesthouse in Windermere
4.94 out of 5 average rating, 242 reviewsSmall Guesthouse near Orlando's Theme Parks
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Guesthouse in Clermont
4.85 out of 5 average rating, 149 reviewsDiscover Tranquility at Our Charming Guest House
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Guesthouse in Mount Dora
4.9 out of 5 average rating, 723 reviewsKey West cottage of Mt Dora
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Guesthouse in College Park
4.97 out of 5 average rating, 379 reviewsThe Coach House- 2 bedroom/3 bath Orlando Getaway!
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Guesthouse in Clear Lake
4.74 out of 5 average rating, 19 reviewsLakefront Guest House by downtown :Boat, Fishing…
Guest house rentals with a patio
![](https://a0.muscache.com/im/pictures/miso/Hosting-33711939/original/c93596fc-dc68-4f88-8e66-bc9f8bbdd9c7.jpeg?im_w=720)
Guesthouse in Orlando
4.89 out of 5 average rating, 149 reviews“The Clementine” Boho Home in Orlando’s Food Scene
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Guesthouse in Delaney Park
4.96 out of 5 average rating, 156 reviewsStylish Private Guest Suite in heart of Orlando
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Guesthouse in Orlando
4.88 out of 5 average rating, 231 reviewsCouples Oasis *Heated Pool* and Lake View
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Guesthouse in Delaney Park
4.89 out of 5 average rating, 114 reviewsDowntown private pool house. Two blocks from ORMC
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Guesthouse in Orlando
4.96 out of 5 average rating, 196 reviewsCharming 1 bedroom Casita with private entrance
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Guesthouse in Orlando
4.94 out of 5 average rating, 148 reviewsHidden Luxury Gem w/ private porch
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Guesthouse in Mount Dora
4.93 out of 5 average rating, 140 reviewsEnjoy downtown: modern studio w/ kitchenette
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Guesthouse in Orlando
5 out of 5 average rating, 30 reviewsLocation, Location, Location!
Guest house rentals with a washer and dryer
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Guesthouse in Orlando
4.96 out of 5 average rating, 259 reviewsPeculiar One bedroom Studio.
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Guesthouse in Sanford
4.95 out of 5 average rating, 234 reviewsPalmetto Pool Retreat
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Guesthouse in Orlando
4.98 out of 5 average rating, 115 reviewsLuxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF
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Guesthouse in College Park
4.93 out of 5 average rating, 231 reviewsBungalow Near Downtown Orlando - No Cleaning Fee!
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Guesthouse in Orlando
4.94 out of 5 average rating, 222 reviewsModern Guest Studio (Private) Pool / Spa available
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Guesthouse in Orlando
4.9 out of 5 average rating, 392 reviewsBungalow Close to Attractions and Downtown Orlando
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Guesthouse in Thornton Park
4.99 out of 5 average rating, 241 reviewsBlack House- Private Cottage in Thornton Park!
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Guesthouse in Mount Dora
4.96 out of 5 average rating, 175 reviewsWalk to Downtown! - The Carriage House
Quick stats about guesthouse rentals in Winter Park
Total rentals
30 properties
Total number of reviews
2.6K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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