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Search results; Over 1,000 homes in Winter Park

Guest favourite
Bungalow in Winter Park
Cozy 2/2 Home - Downtown Winterpark/Orlando
2 bedrooms, 2 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.97 out of 5 average rating, 352 reviews
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
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
21–26 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, 29 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
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 63 reviews
Guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
22–27 Nov
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Treehouse in Orlando
Brand New Stylish & Unique Tree House!
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 78 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 105 reviews
Home in Orlando
Pool Home + BBQ Grill + Family Friendly
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
17–24 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Guest suite in Altamonte Springs
Guest Suite! Key West in Altamonte Springs!
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 446 reviews
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps 6, Pool&Gym
2 bedrooms, 3 beds, 2 bathrooms
22–27 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
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
11–16 Oct
Top guest favourite
Bungalow in Orlando
Den on Daniels
1 bedroom, 1 bed, 1 bathroom
22–27 Aug
4.98 out of 5 average rating, 142 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
18–23 Sept
4.97 out of 5 average rating, 477 reviews
Top guest favourite
Guest suite in Orlando
~Chic Oasis • 6-Guest Suite • Pool Heat • Near All
2 bedrooms, 3 beds, 1 bathroom
27 Nov – 2 Dec
4.98 out of 5 average rating, 445 reviews