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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Flat in Winter Park
Apt C -Modern Elegance in the Heart of Winter Park
2 bedrooms, 2 beds, 2 private bathrooms
24–29 Jul
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4.96 out of 5 average rating, 227 reviews
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
2 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 61 reviews
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 77 reviews
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bathroom
31 Jul – 5 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Orlando
Lake Eola Retreat + Private Hot Tub & Yard + Grill
2 bedrooms, 2 beds, 1.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Bungalow in Orlando
Den on Daniels
1 bedroom, 1 bed, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 135 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
5.0 out of 5 average rating, 37 reviews
Superhost
Hotel in Winter Park
Large marble bathroom & Julius Meinl coffeemaker
1 bedroom, 1 king bed, 1 bathroom
1–6 Jul
Guest favourite
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
22–27 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Orlando
2 King Beds • Minutes to AdventHealth + Downtown
2 bedrooms, 2 king beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Orlando
Tropical Oasis|Lounge|Putting Green|Heated Pool
3 bedrooms, 6 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
17–22 Oct
4.98 out of 5 average rating, 41 reviews
Home in Kissimmee
Orlando Dream Escape | Private Pool | Disney
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Orlando
Home New Cozy & Stylish sleep5/2bath primelocation
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
1–6 Jul
5.0 out of 5 average rating, 211 reviews
Top guest favourite
Guest house in Orlando
College Park Villa Oasis w/ Botanical Courtyard
1 bedroom, 1 queen bed, 1 bathroom
4–9 Jul
4.99 out of 5 average rating, 168 reviews
Top guest favourite
Home in Longwood
Central Florida Pool Home
3 bedrooms, 2 beds, 2 bathrooms
17–22 Jul
4.96 out of 5 average rating, 52 reviews