House holiday rentals in Winter Park
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Top-rated house rentals in Winter Park
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Park house rentals
House rentals with a pool
Home in Orlando
4.91 out of 5 average rating, 117 reviewsLakefront presidential suite / resort pool
9–16 Jun
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
20–27 Dec
Home in Orlando
4.94 out of 5 average rating, 123 reviewsThe Orlando Retreat.
21–28 Aug
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
22–29 Jul
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
16–23 Jun
Home in Sanford
4.86 out of 5 average rating, 214 reviewsPrivate Pool at Flamingo Cottage
22–29 Jan
Home in Oviedo
4.92 out of 5 average rating, 283 reviews4 bedroom Modern pool home, close to UCF&Boombah
7–14 Mar
Home in Orlando
4.85 out of 5 average rating, 131 reviewsYear around Heated Pool 7 min from Airport!
9–16 Jan
Weekly house rentals
Home in Orlando
4.92 out of 5 average rating, 102 reviewsSODO Mid Century Modern Cottage
17–24 Jul
Home in Orlando
4.81 out of 5 average rating, 151 reviewsKing suite , Modern house perfect for vacation
6–13 Dec
Home in Orlando
4.94 out of 5 average rating, 374 reviewsPet Welcome/Fully Fenced Backyard/Washer & Dryer
30 Nov – 7 Dec
Home in Orlando
4.87 out of 5 average rating, 131 reviewsHot Tub, Fire Pit, Private Backyard, King Bed
7–14 Aug
Home in Orlando
4.81 out of 5 average rating, 270 reviewsCharming Central Orlando Home w Private Yard Porch
11–18 Jul
Home in Winter Park
4.84 out of 5 average rating, 102 reviewsModern 4 Bed Home in Winter Park (FullSail/UCF)
4–11 Jun
Home in Leesburg
4.97 out of 5 average rating, 221 reviewsPeace and Quiet
27 Jun – 4 Jul
Home in Orlando
4.97 out of 5 average rating, 138 reviewsDowntown Orlando -The Modern Zen Studio w/Hot Tub
4–11 Aug
Private house rentals
Home in Winter Park
4.8 out of 5 average rating, 40 reviewsNEW! ☀Bungalow+Patio+FirePit! Close to Everything!
12–19 Jun
Home in Orlando
4.95 out of 5 average rating, 19 reviewsColonialtown Bungalow
25 Jan – 1 Feb
Home in Winter Park
4.96 out of 5 average rating, 25 reviewsCharming Retreat In Winter Park
19–26 Aug
Home in Orlando
4.98 out of 5 average rating, 49 reviewsMaison Luxe
9–16 Oct
Home in Orlando
4.91 out of 5 average rating, 34 reviewsCity Charmer
14–21 Jun
Home in Orlando
4.96 out of 5 average rating, 27 reviewsCharming 2BR Cottage, Downtown Orlando
9–16 Jul
Home in Maitland
5.0 out of 5 average rating, 22 reviewsFern Park Retreat
8–15 Aug
Home in Orlando
4.92 out of 5 average rating, 64 reviewsCozy Home near Dtwn w/ Parking
20–27 Jul
Quick stats about house rentals in Winter Park
Total rentals
190 properties
Rentals with dedicated workspaces
120 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
130 properties are a good fit for families
Total number of reviews
4.6K reviews
Destinations to explore
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