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Search results; Over 1,000 homes in Winter Park

Home in Winter Park
Gem. Downtown Winter park, walk to Park av/Rollins
3 bedrooms, 6 beds, 2 private bathrooms
2–7 Oct
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4.9 out of 5 average rating, 143 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 7 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
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 41 reviews
Home in Orlando
Luxury 2BR Home | Private Patio & Stylish Stay
2 bedrooms, 2 king beds, 1 bathroom
25–30 Sept
New place to stay
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Tiny home in Orlando
Tiny Home w/ Parking & Laundry, near UCF & Airport
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Orlando
The Saphire, Milk District Gem! Unit 1
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Orlando
Spacious 2BR Oasis, Sleeps 8 Near Orlando Parks
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Orlando
Updated 2 Bdr • Close to Downtown + Advent Health
2 bedrooms, 2 king beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Home in Kissimmee
Bloom & Roam — Where Comfort Meets Vacation
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
New place to stay
Home in Orlando
Fern Haven at Baldwin | Cozy Urban Retreat
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Flat in Orlando
Private 2-Queen Apt Near MCO with Patio
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 4 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, 112 reviews
Top guest favourite
Guest house in Orlando
Guest Home| Orlando Airport & Florida Mall 15 min
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Guest house in Orlando
College Park Villa Oasis w/ Botanical Courtyard
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 171 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