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.
Jul 27 – Aug 3
Home in Orlando
4.94 out of 5 average rating, 125 reviewsThe Orlando Retreat.
Mar 19 – 26
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
Mar 16 – 23
Home in Mount Dora
4.94 out of 5 average rating, 109 reviewsModern Farmhouse & Pool in Mount Dora by Lake Ola
Aug 12 – 19
Home in Oviedo
4.92 out of 5 average rating, 284 reviews4 bedroom Modern pool home, close to UCF&Boombah
Oct 21 – 28
Home in Orlando
4.87 out of 5 average rating, 166 reviews*Lakefront Pool Home *paddleboard*kayak*game room*
Jul 7 – 14
Home in Orlando
4.83 out of 5 average rating, 137 reviewsPrivate Luxury Pool / Swim up bar / Smart-home
Sep 13 – 20
Home in Edgewood
4.93 out of 5 average rating, 150 reviewsTropical Paradise in the heart of Orlando
Nov 17 – 24
Weekly house rentals
Home in Orlando
4.97 out of 5 average rating, 139 reviewsDowntown Orlando -The Modern Zen Studio w/Hot Tub
Oct 7 – 14
Home in Orlando
4.82 out of 5 average rating, 156 reviewsKing suite , Modern house perfect for vacation
Jan 16 – 23
Home in Orlando
4.82 out of 5 average rating, 273 reviewsCharming Central Orlando Home w Private Yard Porch
May 22 – 29
Home in Winter Park
4.84 out of 5 average rating, 102 reviewsModern 4 Bed Home in Winter Park (FullSail/UCF)
Jun 23 – 30
Home in Orlando
4.82 out of 5 average rating, 157 reviewsLUXURY 𝕄𝕠𝕕𝕖𝕣𝕟 𝔽𝕒𝕣𝕞𝕙𝕠𝕦𝕤𝕖 𝙲𝚁𝚎𝚊𝚃𝚒𝚅𝚎 𝙷𝚞𝙱 near DOWNTOWN
Aug 13 – 20
Home in Sanford
4.97 out of 5 average rating, 212 reviewsClean, cozy home in a GREAT location
Apr 28 – May 5
Home in Orlando
4.94 out of 5 average rating, 376 reviewsPet Welcome/Fully Fenced Backyard/Washer & Dryer
Sep 29 – Oct 6
Home in Winter Park
5.0 out of 5 average rating, 11 reviewsNewly Renovated 2 Bed/2Bath, Fully Furnished Home
Aug 14 – 21
Private house rentals
Home in Orlando
4.98 out of 5 average rating, 50 reviewsLuxe House
Sep 11 – 18
Home in Winter Park
4.91 out of 5 average rating, 43 reviewsꜱʟᴇᴇᴘꜱ 4, ᴡɪɴᴛᴇʀ ᴘᴀʀᴋ & ᴅᴏᴡɴᴛᴏᴡɴ
Oct 15 – 22
Home in Orlando
4.91 out of 5 average rating, 35 reviewsCity Charmer
Aug 7 – 14
Home in Orlando
4.93 out of 5 average rating, 59 reviewsYale House in College Park 2 mi from Downtown
Aug 22 – 29
Home in Orlando
5.0 out of 5 average rating, 34 reviewsLuxurious and modern cottage near UCF
Oct 4 – 11
Home in Orlando
4.97 out of 5 average rating, 31 reviewsCharming 2BR Cottage, Downtown Orlando
Jul 8 – 15
Home in Casselberry
5.0 out of 5 average rating, 46 reviewsSpacious 3 BR Home Perfect for Orlando Getaway
Oct 21 – 28
Home in Maitland
5.0 out of 5 average rating, 27 reviewsFlorida Poolside Paradise a Great Place to Unwind!
Sep 6 – 13
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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