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Search results; Over 1,000 homes in Winter Park

Guest favourite
Room in Winter Park
Winter Park, cozy small room.
1 bedroom, 1 bed, 1 shared bathroom
12–17 Aug
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4.88 out of 5 average rating, 333 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 5 reviews
Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds
10–15 Aug
New place to stay
Top guest favourite
Home in Winter Park
Luxurious 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds
2–7 Sept
5.0 out of 5 average rating, 28 reviews
Guest favourite
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed
18–23 Sept
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 queen beds
7–13 Nov
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps 6, Pool&Gym
2 bedrooms, 3 beds
14–19 Aug
New place to stay
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds
21–26 Aug
New place to stay
Home in Orlando
The Lullaby Retreat | Wekiva & Winter Park
2 bedrooms, 2 beds
13–18 Aug
New place to stay
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds
5–10 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Bungalow in Orlando
Spacious Home in Orlando 1 King 1 Queen
2 bedrooms, 2 beds
11–16 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds
20–25 Aug
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds
12–17 Aug
5.0 out of 5 average rating, 213 reviews
Guest favourite
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
3 bedrooms, 4 beds
13–18 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Orlando
Spacious 2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds
22–27 Nov
4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
22–27 Aug
5.0 out of 5 average rating, 12 reviews