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
4.94 out of 5 average rating, 124 reviewsThe Orlando Retreat.
20 – 27 Apr
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
25 Aug – 1 Sept
Home in Oviedo
4.92 out of 5 average rating, 283 reviews4 bedroom Modern pool home, close to UCF&Boombah
3 – 10 Aug
Home in Orlando
4.88 out of 5 average rating, 165 reviews*Lakefront Pool Home *paddleboard*kayak*game room*
7 – 14 July
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
22 – 29 Apr
Home in Sanford
4.86 out of 5 average rating, 214 reviewsPrivate Pool at Flamingo Cottage
26 Dec – 2 Jan
Home in Orlando
4.83 out of 5 average rating, 137 reviewsPrivate Luxury Pool / Swim up bar / Smart-home
26 July – 2 Aug
Home in Orlando
4.95 out of 5 average rating, 314 reviews*HALF HOME* (read desc) Pool/Disney/Universal
4 – 11 Sept
Weekly house rentals
Home in Orlando
4.9 out of 5 average rating, 104 reviewsSODO Mid Century Modern Cottage
2 – 9 July
Home in Altamonte Springs
4.97 out of 5 average rating, 277 reviewsEclectic Home Where Luxury Meets Affordability
24 – 31 July
Home in Orlando
4.87 out of 5 average rating, 131 reviewsHot Tub, Fire Pit, Private Backyard, King Bed
3 – 10 Oct
Home in Orlando
4.82 out of 5 average rating, 272 reviewsCharming Central Orlando Home w Private Yard Porch
20 – 27 Sept
Home in Orlando
4.94 out of 5 average rating, 376 reviewsPet Welcome/Fully Fenced Backyard/Washer & Dryer
25 Aug – 1 Sept
Home in Orlando
4.82 out of 5 average rating, 153 reviewsKing suite , Modern house perfect for vacation
27 Nov – 4 Dec
Home in Orlando
4.83 out of 5 average rating, 176 reviewsWaterside Pet Friendly Lakefront
16 – 23 Apr
Home in Sanford
4.97 out of 5 average rating, 212 reviewsClean, cozy home in a GREAT location
21 – 28 Apr
Private house rentals
Home in Orlando
4.85 out of 5 average rating, 20 reviewsLuxury 3BD in Downtown Orlando
2 – 9 Sept
Home in Orlando
4.95 out of 5 average rating, 20 reviewsColonialtown Bungalow
5 – 12 Oct
Home in Winter Park
4.96 out of 5 average rating, 25 reviewsFunky Remodeled Otown Bungalow Sleeps8
4 – 11 July
Home in Winter Park
5.0 out of 5 average rating, 17 reviewsMillion Dollar View on the Lake
13 – 20 Apr
Home in Winter Park
4.84 out of 5 average rating, 19 reviewsWinter Park - Cozy retreat near Lake Killarney
2 – 9 June
Home in Orlando
4.91 out of 5 average rating, 35 reviewsCity Charmer
17 – 24 June
Home in Orlando
4.98 out of 5 average rating, 49 reviewsLuxe House
22 – 29 July
Home in Orlando
4.92 out of 5 average rating, 65 reviewsCozy Home near Dtwn w/ Parking
20 – 27 July
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
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Tampa Holiday rentals
- Anna Maria Island Accommodation & holiday rentals
- Sarasota Holiday rentals
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