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 Winter Park
4.87 out of 5 average rating, 104 reviewsComfy 3 Bedrooms - 2 Bathrooms home with pool.
Oct 31 – Nov 7
Home in Orlando
4.91 out of 5 average rating, 117 reviewsLakefront presidential suite / resort pool
May 28 – Jun 4
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
Jun 10 – 17
Home in Orlando
4.94 out of 5 average rating, 123 reviewsThe Orlando Retreat.
Feb 23 – Mar 2
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
Sep 15 – 22
Home in Oviedo
4.92 out of 5 average rating, 283 reviews4 bedroom Modern pool home, close to UCF&Boombah
Mar 27 – Apr 3
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
Jun 16 – 23
Home in Sanford
4.86 out of 5 average rating, 214 reviewsPrivate Pool at Flamingo Cottage
Apr 7 – 14
Weekly house rentals
Home in Orlando
4.92 out of 5 average rating, 102 reviewsSODO Mid Century Modern Cottage
Jul 17 – 24
Home in Orlando
4.81 out of 5 average rating, 151 reviewsKing suite , Modern house perfect for vacation
Dec 23 – 30
Home in Orlando
4.81 out of 5 average rating, 270 reviewsCharming Central Orlando Home w Private Yard Porch
Dec 8 – 15
Home in Winter Park
4.84 out of 5 average rating, 102 reviewsModern 4 Bed Home in Winter Park (FullSail/UCF)
Jun 4 – 11
Home in Orlando
4.83 out of 5 average rating, 175 reviewsWaterside Pet Friendly Lakefront
Sep 18 – 25
Home in Orlando
4.97 out of 5 average rating, 138 reviewsDowntown Orlando -The Modern Zen Studio w/Hot Tub
Aug 4 – 11
Home in Leesburg
4.97 out of 5 average rating, 221 reviewsPeace and Quiet
Jun 27 – Jul 4
Home in Winter Park
5.0 out of 5 average rating, 11 reviewsNewly Renovated 2 Bed/2Bath, Fully Furnished Home
Sep 22 – 29
Private house rentals
Home in Winter Park
5.0 out of 5 average rating, 13 reviewsSpacious 1BD-3min to Winter Park 15.min to Springs
Jul 11 – 18
Home in Orlando
4.98 out of 5 average rating, 49 reviewsLuxe House
Sep 15 – 22
Home in Winter Park
4.9 out of 5 average rating, 70 reviews𝕊𝕝𝕖𝕖𝕡𝕤 𝟠| 𝕎𝕚𝕟𝕥𝕖𝕣 ℙ𝕒𝕣𝕜|ᴏʀʟᴀɴᴅᴏ
Jul 24 – 31
Home in Orlando
4.96 out of 5 average rating, 27 reviewsCharming 2BR Cottage, Downtown Orlando
Jul 7 – 14
Home in Orlando
4.91 out of 5 average rating, 35 reviewsCity Charmer
Oct 4 – 11
Home in Orlando
4.92 out of 5 average rating, 65 reviewsCozy Home near Dtwn w/ Parking
Jul 20 – 27
Home in Maitland
5.0 out of 5 average rating, 23 reviewsFern Park Retreat
Aug 8 – 15
Home in Orlando
5.0 out of 5 average rating, 31 reviewsLuxurious and modern cottage near UCF
Sep 29 – Oct 6
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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