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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Flat in Winter Park
Apt C -Modern Elegance in the Heart of Winter Park
2 bedrooms, 2 beds, 2 private bathrooms
24–29 Jul
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4.96 out of 5 average rating, 227 reviews
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
2 bedrooms, 4 beds, 2 bathrooms
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, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 61 reviews
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 77 reviews
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bathroom
2–9 Jul
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Orlando
Pet friendly pool home in milk district!
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Orlando
3BR Stylish King Family• Pets • Pool • Gym Near Ep
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
5.0 out of 5 average rating, 37 reviews
Hotel in Altamonte Springs
Minutes to Kia Center + Breakfast. Kitchen. Pool.
2 bedrooms, 2 king beds, 2 bathrooms
4–9 Jul
New place to stay
Top guest favourite
Home in Orlando
New Cozy & Stylish Home sleep5/2bath primelocation
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed, 1 bathroom
17–22 Jul
5.0 out of 5 average rating, 133 reviews
Top guest favourite
Tiny home in Orlando
Renovated cozy efficiency with kitchenette
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Longwood
Central Florida Pool Home
3 bedrooms, 2 beds, 2 bathrooms
17–22 Jul
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Guest house in Orlando
The Cottage A Pet Friendly Guesthouse
1 bedroom, 1 king bed, 1 bathroom
23–28 Jul
4.98 out of 5 average rating, 130 reviews
Flat in Orlando
Cozy 2BR Apt | Near Universal & International Dr
2 bedrooms, 4 beds, 2 bathrooms
11–16 Aug
New place to stay
Superhost
Home in Orlando
Orlando Home Near Boombah Sports Plex & Universal
3 bedrooms, 5 beds, 2 bathrooms
1–6 Jul
Superhost
Flat in Kissimmee
Disneys Hot Tub & Themed Home! Only mins to Disney
2 bedrooms, 3 beds, 2.5 bathrooms
1–6 Jul
New place to stay