filters

Search results; Over 1,000 homes in Winter Park

Photo 1 of 29
Top guest favourite
Cottage in Winter Park
Winter Park Pearl 6 min drive to historic Park Ave
3 bedrooms, 3 beds, 1.5 private bathrooms
19–24 Sept
,
4.95 out of 5 average rating, 467 reviews
Photo 1 of 10
Guest house in Winter Park
Private Winter Park Studio with Parking
1 bed, 1 bathroom
20–25 Sept
New place to stay
Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 11
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Top guest favourite
Guest house in Winter Park
Vibrant cottage in charming, unique Florida town
1 bedroom, 1 queen bed, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 10 reviews
Photo 1 of 29
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
Photo 1 of 12
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 143 reviews
Photo 1 of 22
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
Photo 1 of 20
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 Nov
4.98 out of 5 average rating, 482 reviews
Photo 1 of 17
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 215 reviews
Photo 1 of 24
Guest house in Orlando
The Serene Suite Orlando
1 bedroom, 1 queen bed, 1 bathroom
30 Sept – 5 Oct
New place to stay
Photo 1 of 29
Guest favourite
Home in Orlando
College Park • 2 Kings • WorkSpace • AdventHealth
2 bedrooms, 2 king beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 6 reviews
Photo 1 of 8
Top guest favourite
Home in Orlando
The Saphire, Milk District Gem! Unit 1
1 bedroom, 1 bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 30 reviews
Photo 1 of 10
Superhost
Flat in Orlando
Modern 2 bed Near Downtown & Attractions
2 bedrooms, 2 queen beds, No bathroom
20–25 Sept
New place to stay
Photo 1 of 29
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 42 reviews
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Guest house in Orlando
1924 Spanish Carriage House Lower
1 bedroom, 2 beds, 1 bathroom
8–13 Oct
4.98 out of 5 average rating, 155 reviews
Photo 1 of 19
Home in Orlando
Cozy Orlando Getaway
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews