House vacation 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.
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
4.95 out of 5 average rating, 129 reviewsThe Orlando Retreat.
Home in Winter Park
4.87 out of 5 average rating, 104 reviewsComfy 3 Bedrooms - 2 Bathrooms home with pool.
Home in Orlando
4.92 out of 5 average rating, 124 reviewsLakefront presidential suite / resort pool
Home in Mount Dora
4.95 out of 5 average rating, 114 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
Home in Edgewood
4.93 out of 5 average rating, 154 reviewsTropical Paradise in the heart of Orlando
Home in Sanford
4.87 out of 5 average rating, 217 reviewsPrivate Pool at Flamingo Cottage
Home in Kissimmee
4.85 out of 5 average rating, 209 reviews3 bedroom Villa in Kissimmee
Home in Orlando
4.88 out of 5 average rating, 171 reviews*Lakefront Pool Home *paddleboard*kayak*game room*
Weekly house rentals
Home in Orlando
4.95 out of 5 average rating, 180 reviewsStylish New 1 Bed + Office βΌ In Downtown Orlando
Home in Orlando
4.9 out of 5 average rating, 107 reviewsSODO Mid Century Modern Cottage
Home in Orlando
4.92 out of 5 average rating, 102 reviewsI'm On Vacation - Vibey, Fun, & Bright Dtown Spot
Home in Orlando
4.94 out of 5 average rating, 105 reviewsβ Modern DT 2/1πKing BedβLong Staysβ‘οΈWiFiπΊNetflixβ
Home in Winter Garden
4.92 out of 5 average rating, 170 reviewsCozy Winter Garden Home 20 MINUTES FROM DISNEY
Home in Winter Park
4.85 out of 5 average rating, 105 reviewsModern 4 Bed Home in Winter Park (FullSail/UCF)
Home in Orlando
4.82 out of 5 average rating, 276 reviewsCharming Central Orlando Home w Private Yard Porch
Home in Orlando
4.82 out of 5 average rating, 160 reviewsLUXURY ππ πππ£π π½ππ£πππ π¦π€π π²ππππππ π π·ππ± near DOWNTOWN
Private house rentals
Home in Orlando
5.0 out of 5 average rating, 17 reviewsThe Studio in the Heart of Orlando
Home in Maitland
5.0 out of 5 average rating, 23 reviewsFern Park Retreat
Home in Orlando
4.98 out of 5 average rating, 56 reviewsLuxe House
Home in Casselberry
5.0 out of 5 average rating, 50 reviewsSpacious 3 BR Home Perfect for Orlando Getaway
Home in Winter Park
4.97 out of 5 average rating, 38 reviewsCozy Winter Park Home
Home in Winter Park
4.98 out of 5 average rating, 43 reviewsSpacious & lovely 3 bedroom Winter Park home
Home in Orlando
5.0 out of 5 average rating, 10 reviewsUptown Orlando Mid-Century Hub
Home in Winter Park
4.91 out of 5 average rating, 33 reviewsCharming Retreat In Winter Park
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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- Family travel hubΒ Tips and inspiration
- Family budget travelΒ Get there for less
- Vacation ideas for any budgetΒ Make it special without making it spendy
- Travel Europe on a budgetΒ How to take the kids to Europe for less
- Outdoor adventureΒ Explore nature with the family
- Bucket list national parksΒ Must-see parks for family travel
- Kid-friendly state parksΒ Check out these family-friendly hikes