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
Treehouse in Saint Cloud
4.97 out of 5 average rating, 793 reviewsTreeHouse in the Cloud, (Close toTheme Parks
19–26 Mar
€ 180 per night
Superhost
Guest house in Winter Park
4.92 out of 5 average rating, 266 reviewsTiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks
13–20 Jul
€ 119 per night
Guest favourite
Guest house in Orlando
5.0 out of 5 average rating, 155 reviewsThe Sacred Space Downtown Orlando Milk District
15–22 Aug
€ 121 per night
Guest favourite
Guest house in Orlando
4.93 out of 5 average rating, 161 reviewsPrivate Backyard Cottage in Mills50
13–20 Aug
€ 111 per night
Guest favourite
Guest house in Orlando
4.91 out of 5 average rating, 145 reviews8th Green Cottage - A relaxing oasis in the city
11–18 Oct
€ 153 per night
Guest favourite
Guest suite in Winter Park
4.96 out of 5 average rating, 245 reviewsAtmospheric Studio in the Garden
15–22 Jun
€ 131 per night
Guest favourite
Guest house in Orlando
4.98 out of 5 average rating, 149 reviewsThe Loft in College Park
19–26 Sep
€ 91 per night
Guest favourite
Loft in Orlando
4.87 out of 5 average rating, 1103 reviewsDowntown (Ivanhoe Village) Loft Apartment
9–16 Aug
€ 105 per night
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
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- Rentals with a patio Winter Park
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- Rentals with a hot tub Winter Park
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- Family-friendly rentals Winter Park
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