Holiday rentals in Winter Park
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Top-rated holiday rentals in Winter Park
Guests agree: these stays are highly rated for location, cleanliness and more.
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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
Guest favourite
Guest house in Orlando
4.97 out of 5 average rating, 155 reviewsThe Loft in College Park
Guest favourite
Tiny home in Orlando
4.96 out of 5 average rating, 627 reviewsQuiet Shed in Downtown
Guest favourite
Guest house in Orlando
4.92 out of 5 average rating, 166 reviewsPrivate Backyard Cottage in Mills50
Guest favourite
Home in Orlando
4.91 out of 5 average rating, 191 reviewsCozy Milk District Home | Downtown | Free Parking
Superhost
Flat in Maitland
4.82 out of 5 average rating, 289 reviewsAt Mine | Elegant Double Suite in North Orlando
Guest favourite
Guest house in Maitland
4.98 out of 5 average rating, 121 reviewsPrivate 1-bd Mid-Century Guesthouse
Guest favourite
Guest house in Winter Park
4.82 out of 5 average rating, 235 reviewsWELCOME HOME IN WINTER PARK
Guest favourite
Guest house in Orlando
4.9 out of 5 average rating, 626 reviewsThornton Park's Historic Guest House - private
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
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Tampa Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- West Palm Beach Holiday rentals
- Boca Raton Holiday rentals
- Naples Holiday rentals
- Fort Lauderdale Holiday rentals
- Miami Beach Holiday rentals
- Miami Holiday rentals
- Key West Holiday rentals
- Private suite rentals Winter Park
- Fitness-friendly rentals Winter Park
- Rentals with an EV charger Winter Park
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- Rentals with a fireplace Winter Park
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- Guest house rentals Winter Park
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- Rentals with a hot tub Winter Park
- Family-friendly rentals Winter Park
- Rentals with a washing machine and dryer Winter Park
- Rentals with lake access Winter Park
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