Holiday rentals in Winter Park
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Top-rated holiday rentals in Winter Park
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Park holiday rentals
Other great holiday rentals in Winter Park
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Quiet Shed in Downtown
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Tiny home in Baldwin Park
Sunset Lakefront View King Bed, Free Bikes Kayaks
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Guest house in College Park
8th Green Cottage - A relaxing oasis in the city
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Rental unit in Maitland
At Mine | Elegant Double Suite in North Orlando
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Guest suite in College Park
A SUITE RETREAT with a Garden View in the City
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Home in East Central Park
Cozy Milk District Home | Downtown | Free Parking
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Guest house in Orlando
Treehouse Inn Downtown Orlando, 2 bedrooms 2 bath
Superhost
Guest suite in Winter Park
Modern and Gorgeous Apt Studio 1b1b at Winter Park
Quick stats about holiday 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
Destinations to explore
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- Rentals with a fireplace Winter Park
- Rentals with an EV charger Winter Park
- House rentals Winter Park
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- Rentals with pools Winter Park
- Monthly Rentals Winter Park
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- Rentals with lake access Winter Park
- Rentals with a hot tub Winter Park
- Rentals with a washing machine and dryer Winter Park
- Rentals with outdoor seating Winter Park
- Family-friendly rentals Winter Park
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- Rentals with a firepit Winter Park
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- Private suite rentals Winter Park
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- Flat rentals Winter Park
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