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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
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 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
Top 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, 5 reviews
Top guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds, 1 bathroom
12–17 Aug
4.99 out of 5 average rating, 79 reviews
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
Home in Orlando
Hidden Oasis House - Pool, Gameroom in DT Orlando!
3 bedrooms, 5 beds, 2 bathrooms
2–7 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, 38 reviews
Top guest favourite
Home in Longwood
Central Florida Pool Home
3 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
4.96 out of 5 average rating, 54 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
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
New place to stay
Top guest favourite
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 12 reviews
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
New place to stay
Top guest favourite
Townhouse in Orlando
Fun Family Townhome with Pool and Game Room!
5 bedrooms, 9 beds, 5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Kissimmee
Jungle pool home w/ hot tub - close to Disney
4 bedrooms, 7 beds, 3 bathrooms
17–22 Aug
New place to stay
Home in Clermont
Orlando Most Incredible Themed 10BR Villa
10 bedrooms, 14 beds, 8 bathrooms
14–19 Aug
New place to stay
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, 102 reviews