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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, 79 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
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
Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 queen beds, 2 bathrooms
7–13 Nov
4.96 out of 5 average rating, 27 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 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
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
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
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bathroom
5–10 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Orlando
AirPort & Downtown Orlando 15 min| Disney 30 min
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 20 reviews
Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds, 1 bathroom
4–9 Sept
New place to stay
Top guest favourite
Home in Orlando
The Saphire, Milk District Gem! Unit 1
1 bedroom, 1 bed, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 30 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, 46 reviews
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
4–9 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps6, Pool & Gym
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 5 reviews
Flat in Orlando
Private 2-Queen Apt Near MCO with Patio
1 bedroom, 3 beds, 1 bathroom
7–12 Sept
New place to stay
Apartment in Casselberry
Cozy Private Apartment in Casselberry
2 bedrooms, 2 queen beds, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 4 reviews