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Search results; Over 1,000 homes in Winter Park

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
1–6 Aug
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4.95 out of 5 average rating, 463 reviews
Guest favourite
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 bedroom, 1 queen bed
2–7 Aug
4.97 out of 5 average rating, 474 reviews
Top guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom, 1 queen bed
1–6 Aug
4.97 out of 5 average rating, 175 reviews
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
2 bedrooms, 4 beds
3–8 Aug
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds
11–16 Aug
4.99 out of 5 average rating, 80 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
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed
1–6 Aug
5.0 out of 5 average rating, 134 reviews
Superhost
Flat in Orlando
Luxury 1BR & Resort Amenities + 6min to Epic-Unive
1 bedroom, 2 beds
2–7 Aug
New place to stay
Top guest favourite
Place to stay in Orlando
Handicap Accessible Master room
1 bedroom, 1 king bed
27 Jan – 1 Feb
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Orlando
2 King Beds • Minutes to AdventHealth + Downtown
2 bedrooms, 2 king beds
1–6 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Orlando
Sunny Oasis: Downtown Orlando with Suburban feel
2 bedrooms, 2 double beds
4–9 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest house in Orlando
Amazing New Pool House!
1 bedroom, 2 beds
17–22 Aug
4.98 out of 5 average rating, 110 reviews
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed
1–6 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds
3–8 Aug
5.0 out of 5 average rating, 212 reviews
Top guest favourite
Flat in Orlando
Modern Oasis | King Bed • Pool & Gym • Near Epic U
1 bedroom, 2 beds
2–7 Aug
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Guest house in Orlando
Cozy Modern Retreat | Patio | Self Check-In
1 queen bed
5–10 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest suite in Orlando
LAKEFRONT STUDIO APARTMENT (private entrance)
1 bedroom, 1 king bed
1–6 Aug
5.0 out of 5 average rating, 485 reviews