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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
21–26 Aug
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4.95 out of 5 average rating, 466 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 6 reviews
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, 30 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds
24–29 Aug
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds
25–30 Aug
5.0 out of 5 average rating, 39 reviews
Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds
21–26 Aug
New place to stay
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds
11–16 Oct
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
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds
23–30 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Orlando
5 Min- Epic Universe+KingBed+Disney
3 bedrooms, 5 beds
21–26 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
30 Nov – 5 Dec
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Guest house in Orlando
1924 Spanish Carriage House Lower
1 bedroom, 2 beds
29 Aug – 3 Sept
4.98 out of 5 average rating, 149 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
Superhost
Home in Orlando
Colorful little lakefront cottage on 5 acres.
3 bedrooms, 4 beds
21–26 Aug
4.66 out of 5 average rating, 85 reviews
Superhost
Home in Four Corners
8BR house with private pool and game room
8 bedrooms, 8 beds
24–29 Aug
New place to stay