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Search results; Over 1,000 homes in Winter Park

Guest favourite
Bungalow in Winter Park
Charming Farmhouse Bungalow
3 bedrooms, 3 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.82 out of 5 average rating, 113 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Winter Park
Luxurious 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 28 reviews
Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 queen beds, 2 bathrooms
7–13 Nov
4.96 out of 5 average rating, 27 reviews
Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds, 4 bathrooms
16–21 Aug
New place to stay
Guest favourite
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 11 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, 10 reviews
Townhouse in Kissimmee
Magical Family Retreat 4B, 3.5B, Spa, 4M Disney!
4 bedrooms, 8 beds, 3.5 bathrooms
28 Aug – 2 Sept
New place to stay
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
12–17 Aug
5.0 out of 5 average rating, 213 reviews
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps 6, Pool&Gym
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
New place to stay
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds, 2.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Orlando
Spacious 2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
5.0 out of 5 average rating, 135 reviews
Guest favourite
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 4 reviews
Home in Orlando
Pool Home + BBQ Grill + Family Friendly
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 39 reviews