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Search results; Over 1,000 homes in Winter Park

Guest favourite
Bungalow in Winter Park
Charming Farmhouse Bungalow
3 bedrooms, 3 beds, 2 private bathrooms
6–11 Aug
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4.83 out of 5 average rating, 111 reviews
Top guest favourite
Guest house in Orlando
Location, Location, Location!
1 bedroom, 1 bed
12–17 Jul
4.99 out of 5 average rating, 129 reviews
Top guest favourite
Flat in Winter Park
Apt D -Modern Elegance in the Heart of Winter Park
2 bedrooms, 2 queen beds
26–31 Jul
4.96 out of 5 average rating, 232 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds
17–22 Oct
4.98 out of 5 average rating, 41 reviews
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds
31 Jul – 5 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed
9–14 Jul
5.0 out of 5 average rating, 133 reviews
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
2 bedrooms, 4 beds
17–22 Jul
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds
19–24 Jul
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Flat in Orlando
3BR Stylish King Family• Pets • Pool • Gym Near Ep
3 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Guest house in Orlando
Amazing New Pool House!
1 bedroom, 2 beds
29 Jul – 3 Aug
4.98 out of 5 average rating, 107 reviews
Top guest favourite
Home in Orlando
Lake Eola Retreat + Private Hot Tub & Yard + Grill
2 bedrooms, 2 beds
19–24 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Orlando
Sunny Oasis: Downtown Orlando with Suburban feel
2 bedrooms, 2 double beds
13–18 Jul
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds
26–31 Jul
4.99 out of 5 average rating, 77 reviews
Superhost
Hotel in Winter Park
Large marble bathroom & Julius Meinl coffeemaker
1 bedroom, 1 king bed
10–15 Jul
Top guest favourite
Guest house in Orlando
The Cottage A Pet Friendly Guesthouse
1 bedroom, 1 king bed
23–28 Jul
4.98 out of 5 average rating, 130 reviews
Home in Orlando
Walk to Epic Universe | New! 3BR/3.5BA | Vista cay
3 bedrooms, 5 beds
19–24 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds
18–23 Jul
5.0 out of 5 average rating, 37 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds
16–21 Aug
5.0 out of 5 average rating, 96 reviews
Guest favourite
Guest house in Orlando
Cozy Guest House Near MCO & Theme Parks
1 bedroom, 2 beds
13–18 Aug
5.0 out of 5 average rating, 7 reviews