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
5.0 out of 5 average rating, 22 reviews, 2 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
5.0 out of 5 average rating, 61 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Jul
Superhost
Hotel in Winter Park
Large marble bathroom & Julius Meinl coffeemaker
1 bedroom, 1 bed, 1 bathroom
1–6 Jul
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
4.99 out of 5 average rating, 77 reviews, 3 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Guest favourite
Home in Orlando
2 King Beds • Minutes to AdventHealth + Downtown
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Home in Orlando
Lake Eola Retreat + Private Hot Tub + Grill
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
19–24 Jul
Guest house in Orlando
Cozy Studio near to Orlando Airport
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Jul
Villa in Orlando
Charming Orlando Villa with Pool & Family Fun
New place to stay, 4 bedrooms, 6 beds, 2 bathrooms
20–25 Jul
Top guest favourite
Home in Orlando
New Cozy & Stylish Home sleep5/2bath primelocation
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
4.98 out of 5 average rating, 41 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Oct
Top guest favourite
Flat in Orlando
2BR Getaway: Pool, Gym, Pets OK! Sleeps 6 NearEpic
4.96 out of 5 average rating, 25 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–12 Jul
Top guest favourite
Bungalow in Orlando
Den on Daniels
4.98 out of 5 average rating, 135 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
5.0 out of 5 average rating, 37 reviews, 4 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
5.0 out of 5 average rating, 211 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Jul
Superhost
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Guest house in Orlando
The Cottage A Pet Friendly Guesthouse
4.98 out of 5 average rating, 130 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Jul
Home in Kissimmee
Orlando Dream Escape | Private Pool | Disney
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Home in Kissimmee
Aurora Lux| Heated Pool| Games Room| Mini Golf|BBQ
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 6 beds, 2 bathrooms
9–14 Aug