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Search results; Over 1,000 places in Winter Park

Superhost
Flat in Maitland
At Mine | Elegant Double Suite in North Orlando
2 double beds
21–26 Apr
4.82 out of 5 average rating, 250 reviews
Guest favourite
Room in Winter Park
Stay with AdamAerospace engineer,
Pura Vida Home 1
9–14 Oct
4.93 out of 5 average rating, 264 reviews
Superhost
Flat in Maitland
At Mine | King Suite In North Orlando
1 king bed
21–26 Apr
4.76 out of 5 average rating, 106 reviews
Superhost
Apartment in Winter Park
Lovely Winter Park Home close to Hospitals !
2 beds
26 Apr – 1 May
4.81 out of 5 average rating, 57 reviews
Room in Winter Park
Stay with Gustavo
Cozy apartment in Winter Park
18–23 Apr
New place to stay
Guest favourite
Home in Winter Park
Comfy 3 Bedrooms - 2 Bathrooms home with pool.
4 beds
20–25 Apr
4.87 out of 5 average rating, 103 reviews
Guest favourite
Home in Winter Park
Cozy Winter Park Cottage
7 beds
26–31 May
5.0 out of 5 average rating, 20 reviews
Villa in Winter Park
Balfour Villa
22–27 Apr
4.75 out of 5 average rating, 75 reviews
Superhost
Home in Maitland
Bonheur Ala Maison - Boasts beauty comfort extras
4 beds
18–23 Apr
4.82 out of 5 average rating, 85 reviews
Apartment in Winter Park
2 bedr condo close to Winter Park, UCF, Full Sail
4 beds
27 May – 1 Jun
4.69 out of 5 average rating, 108 reviews
Guest favourite
Townhouse in Casselberry
Gorgeous Lake Howell Townhouse
3–8 Jun
4.94 out of 5 average rating, 16 reviews
Home in Maitland
Cheerful 3 Bed home with pool Winter Park/Maitland
4 beds
12–17 May
4.74 out of 5 average rating, 47 reviews
Guest favourite
Home in Winter Park
Winter Park Citrus Escape
6 beds
13–18 May
4.94 out of 5 average rating, 34 reviews
Guest favourite
Home in Maitland
Orlando Tropical Oasis
21–26 Apr
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Orlando
Modern Home w/ Beautiful Pool - 3 Bed/2.5 Bath
3 beds
19–24 Apr
5.0 out of 5 average rating, 3 reviews
Home in Orlando
Casa Lago - Downtown Orlando
8 beds
12–17 May
New place to stay
Guest favourite
Home in Orlando
The Orlando Retreat.
4 beds
9–14 Jun
4.94 out of 5 average rating, 122 reviews
Superhost
Home in Orlando
Villa Pilar | KingBed • Outdoor Kitchen & Dining
4 beds
22–28 Apr
5.0 out of 5 average rating, 18 reviews