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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, 76 reviews
Top guest favourite
Apartment in Winter Park
Walk to Park Ave & The WP Village!
3 bedrooms, 3 beds
1–6 Sept
4.97 out of 5 average rating, 66 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds
6–11 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Winter Park
Luxurious 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds
6–11 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds
20–25 Sept
5.0 out of 5 average rating, 64 reviews
Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 queen beds
7–13 Nov
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds
8–13 Sept
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds
5–10 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Kissimmee
4BR house with private pool in Magic Village
4 bedrooms, 6 beds
1–6 Sept
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Orlando
Modern 2BR Escape | King Bed • Pets • Epic U10 min
2 bedrooms, 3 beds
2–7 Sept
5.0 out of 5 average rating, 44 reviews
Guest suite in Orlando
God’s Peaceful Christian Private Studio w/Bathroom
1 bedroom, 1 queen bed
1–6 Sept
New place to stay
Room in Winter Park
Quiet, comfortable room in Orlando (Winter Park)
1 bed
1–6 Sept
Flat in Orlando
Private Bamboo Oasis Apartment in College Park
1 bedroom, 1 bed
1–6 Sept
Top guest favourite
Home in Orlando
4BR: Lakefront Retreat with Harry Potter Game Loft
4 bedrooms
22–27 Sept
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
18–23 Oct
5.0 out of 5 average rating, 106 reviews
Guest favourite
Home in Kissimmee
Amazing Home Near Parks w/ Pool & Spa
4 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 8 reviews