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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Home in Winter Park
Top 1% Modern Japandi Retreat - Jacuzzi No Fee
4 bedrooms, 6 beds, 3 private bathrooms
7–12 Sept
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4.95 out of 5 average rating, 78 reviews
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
2–7 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 214 reviews
Top guest favourite
Guest house in Orlando
Amazing New Pool House!
1 bedroom, 2 beds, 1 bathroom
2–7 Oct
4.98 out of 5 average rating, 111 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
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
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
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 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
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 Altamonte Springs
Lake Marion Apt w/ Canoe in Altamonte Springs!
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.89 out of 5 average rating, 93 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
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 141 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 41 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
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
Flat in Orlando
Modern 2BR Escape | King Bed • Pets • Epic U10 min
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Guest suite in Orlando
~Chic Oasis • 6-Guest Suite • Pool Heat • Near All
2 bedrooms, 3 beds, 1 bathroom
14–19 Nov
4.97 out of 5 average rating, 449 reviews