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, 559 reviewsCharming Comfortable Cottage in College Park
23–30 Oct
$191 NZD per night
Guest favourite
Guesthouse in Maitland
4.98 out of 5 average rating, 114 reviewsPrivate 1-bd Mid-Century Guesthouse
1–8 Jan
$202 NZD per night
Guest favourite
Guesthouse in Orlando
4.98 out of 5 average rating, 145 reviewsThe Loft in College Park
14–21 Aug
$163 NZD per night
Guest favourite
Guesthouse in Orlando
4.83 out of 5 average rating, 197 reviewsLovely Spacious Guesthouse in Mills 50 District
28 Jan – 4 Feb
$142 NZD per night
Guest favourite
Guest suite in Orlando
4.94 out of 5 average rating, 146 reviewsGuesthouse in Mills 50 w backyard walking to bars
26 May – 2 Jun
$212 NZD per night
Guest favourite
Loft in Orlando
4.86 out of 5 average rating, 1096 reviewsDowntown (Ivanhoe Village) Loft Apartment
4–11 Mar
$188 NZD per night
Guest favourite
Guest suite in Altamonte Springs
4.97 out of 5 average rating, 299 reviewsSt. Hemingway Suite
20–27 Aug
$178 NZD per night
Guest favourite
Guesthouse in Orlando
4.97 out of 5 average rating, 286 reviewsOasis Garden Cottage -cozy, chic, near everything!
19–26 Sep
$227 NZD 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
- 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 a fireplace Winter Park
- Apartment rentals Winter Park
- House rentals Winter Park
- Rentals with an EV charger Winter Park
- Rentals with a washing machine and dryer Winter Park
- Rentals with a patio Winter Park
- Pet-friendly rentals Winter Park
- Rentals with outdoor seating Winter Park
- Rentals with a hot tub Winter Park
- Guesthouse rentals Winter Park
- Rentals with lake access Winter Park
- Condo rentals Winter Park
- Rentals with a fire pit Winter Park
- Family-friendly rentals Winter Park
- Rentals with pools Winter Park
- Kid-friendly rentals Winter Park
- Private suite rentals Winter Park
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- Monthly Rentals Winter Park
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