Apartment holiday rentals in Winter Park
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Top-rated apartment rentals in Winter Park
Guests agree: These apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Winter Park apartment rentals
Weekly apartment rentals
Apartment in Winter Garden
4.97 out of 5 average rating, 225 reviewsLakeview Garden Studio
30 Jun – 7 Jul
Apartment in St. Cloud
4.97 out of 5 average rating, 388 reviewsLake Front Apartment w/ FREE use of Kayaks & Canoe
10–17 Nov
Apartment in Winter Garden
4.88 out of 5 average rating, 111 reviewsStay A While
17–24 Jul
Apartment in Orlando
4.92 out of 5 average rating, 131 reviewsLuxury & Modern Apartment
17–24 Jul
Apartment in Orlando
4.88 out of 5 average rating, 387 reviewsLittle Lulu's House
27 Mar – 3 Apr
Apartment in Orlando
4.88 out of 5 average rating, 257 reviewsCarmen Romantic Studio W/Private Beautiful Terrace
20–27 Aug
Apartment in Orlando
4.95 out of 5 average rating, 160 reviewsPrívate studio apartment
21–28 May
Apartment in Orlando
4.83 out of 5 average rating, 293 reviews✪ Fashionable ✔Location ✔Netflix ✔Parking ✔Wifi
13–20 Mar
Private apartment rentals
Apartment in Winter Park
4.79 out of 5 average rating, 28 reviewsCute and Cozy Apartment 1 Bedroom Duplex - UNIT B
5–12 Dec
Apartment in Orlando
4.89 out of 5 average rating, 18 reviewsThe Calm Blue One - Downtown
21–28 Jul
Apartment in Orlando
4.98 out of 5 average rating, 54 reviewsDT Orlando High-Rise Sunset View - Free Parking
3–10 Sep
Apartment in Orlando
4.93 out of 5 average rating, 15 reviewsModern Luxe Oasis Orlando | King Bed + Fast Wifi
8–15 Oct
Apartment in Orlando
5.0 out of 5 average rating, 71 reviewsParent's Retreat!
24–31 Mar
Apartment in Orlando
4.95 out of 5 average rating, 37 reviewsThornton Park Apartment in Historic District
11–18 Nov
Apartment in Orlando
5.0 out of 5 average rating, 27 reviews"Orlando 1BR Haven"
30 Aug – 6 Sep
Apartment in Orlando
4.8 out of 5 average rating, 50 reviewsEola Heights Hideaway *Downtown Pet Friendly*
11–18 Aug
Apartment rentals with a hot tub
Apartment in Kissimmee
4.88 out of 5 average rating, 266 reviewsKing Bed Family Condo Orlando Disney Universal
19–26 Sep
Apartment in Kissimmee
4.89 out of 5 average rating, 195 reviewsModern Great Villa near Disney & Parks
7–14 Nov
Apartment in Kissimmee
4.92 out of 5 average rating, 110 reviewsBRAND NEW 2BR Apt, 5mi to Disney - Storey Lake 401
23–30 Aug
Apartment in Orlando
4.78 out of 5 average rating, 322 reviewsWestgate Lakes+Spa Studio Sleeps 4
7–14 Nov
Apartment in Kissimmee
4.92 out of 5 average rating, 205 reviewsDisneyWorld - 10min!Perfect 3brm Family Condo
5–12 Jul
Apartment in Orlando
5.0 out of 5 average rating, 18 reviewsModern Living New 2bed 2bath Condo
29 Jan – 5 Feb
Apartment in Orlando
4.84 out of 5 average rating, 64 reviewsPool view Universal & International Dr,DisneyS40W
2–9 May
Apartment in Orlando
4.87 out of 5 average rating, 23 reviewsSuper Location
6–13 Sep
Quick stats about apartment rentals in Winter Park
Total rentals
80 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
4K reviews
Destinations to explore
- Orlando Holiday rentals
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