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Search results; Over 1,000 homes in Winter Park

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
Superhost
Hotel in Winter Park
Large marble bathroom & Julius Meinl coffeemaker
1 bedroom, 1 king bed, 1 bathroom
1–6 Jul
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
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
Guest favourite
Home in Orlando
Lake Eola Retreat + Private Hot Tub + Grill
2 bedrooms, 2 beds, 1.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 14 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
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
Top guest favourite
Home in Orlando
New Cozy & Stylish Home 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 Longwood
Central Florida Pool Home
3 bedrooms, 2 beds, 2 bathrooms
17–22 Jul
4.96 out of 5 average rating, 52 reviews
Villa in Orlando
Charming Orlando Villa with Pool & Family Fun
4 bedrooms, 6 beds, 2 bathrooms
20–25 Jul
New place to stay
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
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
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
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
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 Kissimmee
Aurora Lux| Heated Pool| Games Room| Mini Golf|BBQ
4 bedrooms, 6 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 9 reviews
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bathroom
2–9 Jul
5.0 out of 5 average rating, 3 reviews