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 suite in Orlando
4.93 out of 5 average rating, 560 reviewsCharming Comfortable Cottage in College Park
9–16 Nov
₹8,288 per night
Guest favourite
Guest house in Orlando
4.89 out of 5 average rating, 607 reviewsThornton Park's Historic Guest House - private
15–22 Aug
₹6,662 per night
Guest favourite
Guest suite in Altamonte Springs
4.97 out of 5 average rating, 300 reviewsSt. Hemingway Suite
27 Jul – 3 Aug
₹7,528 per night
Guest favourite
Guest house in Orlando
4.93 out of 5 average rating, 160 reviewsPrivate Backyard Cottage in Mills50
13–20 Aug
₹8,111 per night
Guest favourite
Treehouse in Saint Cloud
4.97 out of 5 average rating, 789 reviewsTreeHouse in the Cloud, (Close toTheme Parks
13–20 Apr
₹14,242 per night
Guest favourite
Guest house in Orlando
4.96 out of 5 average rating, 488 reviewsPrivate Luxurious Apt. - Historic Downtown Orlando
3–10 Oct
₹10,098 per night
Guest favourite
Guest house in Orlando
4.95 out of 5 average rating, 40 reviewsNew Mid Century-Modern Studio
8–15 Jul
₹7,135 per night
Superhost
Apartment in Winter Park
4.81 out of 5 average rating, 58 reviewsLovely Winter Park Home close to Hospitals !
11–18 Jan
₹9,056 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
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
- Rentals with outdoor seating Winter Park
- Rentals with a patio Winter Park
- Rentals with an EV charger Winter Park
- Private suite rentals Winter Park
- Fitness-friendly rentals Winter Park
- Apartment rentals Winter Park
- Rentals with a washing machine and dryer Winter Park
- Rentals with a fireplace Winter Park
- Rentals with a hot tub Winter Park
- House rentals Winter Park
- Pet-friendly rentals Winter Park
- Rentals with lake access Winter Park
- Flat rentals Winter Park
- Guest house rentals Winter Park
- Family-friendly rentals Winter Park
- Rentals with pools Winter Park
- Rentals with a firepit Winter Park
- Family-friendly rentals Winter Park
- Monthly Rentals Winter Park
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