House vacation rentals in Winter Park
Find and book unique houses on Airbnb
Top-rated house rentals in Winter Park
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation 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
4.92 out of 5 average rating, 127 reviewsLakefront presidential suite / resort pool
Home in Orlando
4.95 out of 5 average rating, 131 reviewsThe Orlando Retreat.
Home in Maitland
4.94 out of 5 average rating, 149 reviewsOrlando area pool home in Maitland
Home in Winter Park
4.87 out of 5 average rating, 104 reviewsComfy 3 Bedrooms - 2 Bathrooms home with pool.
Home in Delaney Park
4.91 out of 5 average rating, 103 reviews3,000 Sqft Historic Home with Pool near Downtown
Home in Edgewood
4.93 out of 5 average rating, 157 reviewsTropical Paradise in the heart of Orlando
Home in Apopka
4.87 out of 5 average rating, 100 reviewsCountry Pool home on 2 acres-30 minutes to Disney
Home in Sanford
4.87 out of 5 average rating, 219 reviewsPrivate Pool at Flamingo Cottage
Weekly house rentals
Home in Sanford
4.97 out of 5 average rating, 216 reviewsClean, cozy home in a GREAT location
Home in Orlando
4.92 out of 5 average rating, 103 reviewsI'm On Vacation - Vibey, Fun, & Bright Dtown Spot
Home in Orlando
4.97 out of 5 average rating, 105 reviewsModern 3/1 in Ivanhoe Village - TrendyHome
Home in Orlando
4.9 out of 5 average rating, 109 reviewsSODO Mid Century Modern Cottage
Home in Orlando
4.83 out of 5 average rating, 162 reviewsKing suite , Modern house perfect for vacation
Home in Orlando
4.84 out of 5 average rating, 567 reviewsQuiet and Comfy Orlando Home - Close To It All
Home in Winter Park
4.82 out of 5 average rating, 107 reviewsMills House @WP. Sleeps 11 Renovated. Queen beds
Home in Orlando
4.94 out of 5 average rating, 107 reviews★Modern DT 2/1👑King Bed✔Long Stays⚡️WiFi📺Netflix★
Private house rentals
Home in Winter Park
5 out of 5 average rating, 11 reviewsNewly Renovated 2 Bed/2Bath, Fully Furnished Home
Home in Maitland
5 out of 5 average rating, 25 reviewsFern Park Retreat
Home in Winter Park
5 out of 5 average rating, 19 reviewsMillion Dollar View on the Lake
Home in Baldwin Park
4.93 out of 5 average rating, 42 reviewsCity Charmer
Home in Maitland
5 out of 5 average rating, 33 reviewsFlorida Poolside Paradise a Great Place to Unwind!
Home in Winter Park
4.98 out of 5 average rating, 43 reviewsSpacious & lovely 3 bedroom Winter Park home
Home in Orlando
4.98 out of 5 average rating, 59 reviewsLuxe House
Home in Casselberry
5 out of 5 average rating, 53 reviewsSpacious 3 BR Home Perfect for Orlando Getaway
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
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