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Search results; Over 1,000 homes in Winter Park

Guest favourite
Home in Winter Park
Stylish newly updated home in Winter Park
3 bedrooms, 4 beds, 2 private bathrooms
7–12 Sept
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4.98 out of 5 average rating, 205 reviews
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Winter Park
Walk to Park Ave & The WP Village!
3 bedrooms, 3 beds, 2.5 bathrooms
10–15 Sept
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 214 reviews
Top guest favourite
Bungalow in Orlando
Den on Daniels
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 145 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
30 Nov – 5 Dec
4.98 out of 5 average rating, 52 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Winter Park
2BR 2BA Near Park Ave & Rollins
2 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Guest house in Orlando
Location, Location, Location!
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 135 reviews
Top guest favourite
Home in Orlando
4BR: Lakefront Retreat with Harry Potter Game Loft
4 bedrooms, 3 bathrooms
12–17 Oct
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Flat in Orlando
Modern Oasis | King Bed • Pool & Gym • Near Epic U
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 70 reviews
Guest favourite
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest suite in Altamonte Springs
Guest Suite! Key West in Altamonte Springs!
1 bedroom, 1 queen bed, 1 bathroom
22–27 Sept
4.96 out of 5 average rating, 448 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
9–16 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 65 reviews
Room in Orlando
Orlando Comfort
2 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
4.98 out of 5 average rating, 481 reviews
Top guest favourite
Flat in Orlando
Spacious 2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds, 2.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 8 reviews