Holiday houses 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
$1,209 AUD total
Guest favourite
Guesthouse in Orlando
4.89 out of 5 average rating, 607 reviewsThornton Park's Historic Guest House - private
15 – 22 Aug
$1,054 AUD total
Guest favourite
Guest suite in Altamonte Springs
4.97 out of 5 average rating, 300 reviewsSt. Hemingway Suite
27 July – 3 Aug
$1,122 AUD total
Guest favourite
Guesthouse in Orlando
4.93 out of 5 average rating, 160 reviewsPrivate Backyard Cottage in Mills50
13 – 20 Aug
$1,276 AUD total
Guest favourite
Treehouse in Saint Cloud
4.97 out of 5 average rating, 789 reviewsTreeHouse in the Cloud, (Close toTheme Parks
13 – 20 Apr
$2,071 AUD total
Guest favourite
Guesthouse in Orlando
4.96 out of 5 average rating, 488 reviewsPrivate Luxurious Apt. - Historic Downtown Orlando
3 – 10 Oct
$1,489 AUD total
Guest favourite
Guesthouse in Orlando
4.95 out of 5 average rating, 40 reviewsNew Mid Century-Modern Studio
8 – 15 July
$1,046 AUD total
Superhost
Condo in Winter Park
4.81 out of 5 average rating, 58 reviewsLovely Winter Park Home close to Hospitals !
11 – 18 Jan
$1,560 AUD total
Quick stats about accommodation 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 Accommodation & holiday rentals
- Sarasota Holiday rentals
- West Palm Beach Holiday rentals
- Boca Raton Accommodation & holiday rentals
- Naples Accommodation & holiday rentals
- Fort Lauderdale Accommodation & holiday rentals
- Miami Beach Accommodation & 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
- Condo 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
- Apartment rentals Winter Park
- Guesthouse rentals Winter Park
- Family-friendly rentals Winter Park
- Rentals with pools Winter Park
- Rentals with a fire pit Winter Park
- Kid-friendly rentals Winter Park
- Monthly Rentals Winter Park
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