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.
Holiday rentals for every style
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Popular amenities for Winter Park holiday rentals
Other great holiday rentals in Winter Park
Guest suite in Winter Park
4.83 out of 5 average rating, 103 reviewsModern and Gorgeous Apt Studio 1b1b at Winter Park
21–28 Jan
Guest suite in Altamonte Springs
4.97 out of 5 average rating, 300 reviewsSt. Hemingway Suite
6–13 Aug
Guest house in Orlando
4.96 out of 5 average rating, 488 reviewsPrivate Luxurious Apt. - Historic Downtown Orlando
1–8 Oct
Treehouse in Saint Cloud
4.97 out of 5 average rating, 789 reviewsTreeHouse in the Cloud, (Close toTheme Parks
26 Mar – 2 Apr
Yurt in Orlando
4.96 out of 5 average rating, 221 reviewsLakefront Sunset Yurt King Bed *A/C* Kayaks, Bikes
27 May – 1 Jun
Flat in Maitland
4.81 out of 5 average rating, 259 reviewsAt Mine | Elegant Double Suite in North Orlando
14–21 Sep
Guest house in Orlando
4.93 out of 5 average rating, 160 reviewsPrivate Backyard Cottage in Mills50
13–20 Aug
Guest house in Winter Park
4.92 out of 5 average rating, 266 reviewsTiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks
19–26 Jul
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
18T 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
- Fitness-friendly rentals Winter Park
- Rentals with a patio Winter Park
- Private suite rentals Winter Park
- Rentals with a firepit Winter Park
- Rentals with a fireplace Winter Park
- Flat rentals Winter Park
- Guest house rentals Winter Park
- Family-friendly rentals Winter Park
- Rentals with pools Winter Park
- Rentals with an EV charger Winter Park
- House rentals Winter Park
- Apartment rentals Winter Park
- Family-friendly rentals Winter Park
- Rentals with a washing machine and dryer Winter Park
- Monthly Rentals Winter Park
- Rentals with outdoor seating Winter Park
- Pet-friendly rentals Winter Park
- Rentals with a hot tub Winter Park
- Rentals with lake access Winter Park
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