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