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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, 464 reviews
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
2 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 26 reviews
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds, 1 bathroom
11–16 Aug
4.98 out of 5 average rating, 81 reviews
Guest favourite
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 63 reviews
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
New place to stay
Top guest favourite
Home in Orlando
Sunny Oasis: Downtown Orlando with Suburban feel
2 bedrooms, 2 double beds, 2 bathrooms
4–9 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 45 reviews
Home in Orlando
Hidden Oasis House - Pool, Gameroom in DT Orlando!
3 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Home in Orlando
Walk to Epic Universe | New! 3BR/3.5BA | Vista cay
3 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 103 reviews
Top guest favourite
Bungalow in Orlando
Den on Daniels
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 139 reviews
Top guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 474 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
New place to stay
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