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Search results; Over 1,000 homes in Winter Park

Guest favourite
Apartment in Winter Park
Charming 2/1 Condo on a Lake in Winter Park
2 bedrooms, 2 beds, 1 private bathroom
29 Oct – 3 Nov
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4.95 out of 5 average rating, 39 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
Home in Orlando
Luxury 2BR Home | Private Patio & Stylish Stay
2 bedrooms, 2 king beds, 1 bathroom
25–30 Sept
New place to stay
Apartment in Orlando
4114-306 Spacious 3bd condo at Vista Cay Resort
3 bedrooms, 7 beds, 2 bathrooms
6–11 Oct
New place to stay
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
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
Superhost
Home in Kissimmee
Luxe Family Escape | Pool Oasis Near Disney
4 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
New place to stay
Home in Orlando
Cozy Orlando Getaway
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 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
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
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
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
Room in Oviedo
Modern Oviedo Stay | Cozy & Peaceful Nature Suite
1 queen bed, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 3 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
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Storey Lake (4887 Rc)
4 bedrooms, 6 beds, 3 bathrooms
18–23 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 Kissimmee
Close to everything, spacious, and comfortable
3 bedrooms, 5 beds, 2 bathrooms
31 Oct – 5 Nov
New place to stay