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
4.94 out of 5 average rating, 124 reviewsThe Orlando Retreat.
Feb 26 – Mar 5
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
Apr 17 – 24
Home in Orlando
4.92 out of 5 average rating, 118 reviewsLakefront presidential suite / resort pool
Jun 11 – 18
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
Jul 12 – 19
Home in Oviedo
4.92 out of 5 average rating, 283 reviews4 bedroom Modern pool home, close to UCF&Boombah
Apr 2 – 9
Home in Orlando
4.88 out of 5 average rating, 165 reviews*Lakefront Pool Home *paddleboard*kayak*game room*
Jul 7 – 14
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
Apr 21 – 28
Home in Sanford
4.86 out of 5 average rating, 214 reviewsPrivate Pool at Flamingo Cottage
Mar 11 – 18
Weekly house rentals
Home in Orlando
4.81 out of 5 average rating, 156 reviewsLUXURY 𝕄𝕠𝕕𝕖𝕣𝕟 𝔽𝕒𝕣𝕞𝕙𝕠𝕦𝕤𝕖 𝙲𝚁𝚎𝚊𝚃𝚒𝚅𝚎 𝙷𝚞𝙱 near DOWNTOWN
Jun 3 – 10
Home in Orlando
4.9 out of 5 average rating, 104 reviewsSODO Mid Century Modern Cottage
Jul 7 – 14
Home in Orlando
4.82 out of 5 average rating, 272 reviewsCharming Central Orlando Home w Private Yard Porch
Sep 27 – Oct 4
Home in Orlando
4.82 out of 5 average rating, 153 reviewsKing suite , Modern house perfect for vacation
Dec 2 – 9
Home in Orlando
4.83 out of 5 average rating, 176 reviewsWaterside Pet Friendly Lakefront
Jul 23 – 30
Home in Orlando
4.94 out of 5 average rating, 376 reviewsPet Welcome/Fully Fenced Backyard/Washer & Dryer
Sep 6 – 13
Home in Sanford
4.97 out of 5 average rating, 212 reviewsClean, cozy home in a GREAT location
Apr 21 – 28
Home in Orlando
4.97 out of 5 average rating, 138 reviewsDowntown Orlando -The Modern Zen Studio w/Hot Tub
Jul 16 – 23
Private house rentals
Home in Orlando
4.95 out of 5 average rating, 21 reviewsColonialtown Bungalow
Apr 9 – 16
Home in Winter Park
5.0 out of 5 average rating, 17 reviewsMillion Dollar View on the Lake
Nov 16 – 23
Home in Orlando
4.98 out of 5 average rating, 50 reviewsLuxe House
Sep 11 – 18
Home in Maitland
5.0 out of 5 average rating, 23 reviewsFern Park Retreat
Sep 27 – Oct 4
Home in Orlando
4.91 out of 5 average rating, 35 reviewsCity Charmer
Oct 22 – 29
Home in Orlando
4.97 out of 5 average rating, 30 reviewsCharming 2BR Cottage, Downtown Orlando
Jul 7 – 14
Home in Casselberry
5.0 out of 5 average rating, 46 reviewsSpacious 3 BR Home Perfect for Orlando Getaway
Oct 18 – 25
Home in Orlando
5.0 out of 5 average rating, 33 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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