Vacation rentals in Winter Park
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Top-rated vacation rentals in Winter Park
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Vacation rentals for every style
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Popular amenities for Winter Park vacation rentals
Other great vacation rentals in Winter Park
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Tiny homes in Orlando
4.94 out of 5 average rating, 158 reviewsSunset Lakefront View King Bed, Free Bikes Kayaks
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Guesthouse in Orlando
4.93 out of 5 average rating, 229 reviewsBungalow Near Downtown Orlando - No Cleaning Fee!
Guest favourite
Guest suite in Orlando
4.98 out of 5 average rating, 307 reviewsA SUITE RETREAT with a Garden View in the City
Guest favourite
Guesthouse in Orlando
4.84 out of 5 average rating, 202 reviewsLovely Spacious Guesthouse in Mills 50 District
Guest favourite
Guesthouse in Maitland
4.98 out of 5 average rating, 119 reviewsPrivate 1-bd Mid-Century Guesthouse
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Tiny homes in Orlando
4.96 out of 5 average rating, 623 reviewsQuiet Shed in Downtown
Guest favourite
Guesthouse in Orlando
4.96 out of 5 average rating, 491 reviewsPrivate Luxurious Apt. - Historic Downtown Orlando
Guest favourite
Guest suite in Orlando
4.96 out of 5 average rating, 245 reviewsUnique Place! East End Market! Baldwin/Winter Park
Quick stats about vacation rentals in Winter Park
Total rentals
410 properties
Rentals with dedicated workspaces
240 properties have a dedicated workspace
Rentals with a pool
110 properties have a pool
Pet-friendly rentals
140 properties allow pets
Family-friendly rentals
200 properties are a good fit for families
Total number of reviews
18K reviews
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- Rentals with a fireplace Winter Park
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