filters

Search results; Over 1,000 homes in Winter Park

Top guest favourite
Flat in Winter Park
Apt D -Modern Elegance in the Heart of Winter Park
2 bedrooms, 2 queen beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 232 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, 3 reviews
Superhost
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.99 out of 5 average rating, 78 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 63 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, 24 reviews
Home in Orlando
Hidden Oasis House - Pool, Gameroom in DT Orlando!
3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
22–29 Jul
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 101 reviews
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, 37 reviews
Top guest favourite
Bungalow in Orlando
Den on Daniels
1 bedroom, 1 bed, 1 bathroom
25–30 Jul
4.98 out of 5 average rating, 139 reviews
Top guest favourite
Guest house in Orlando
The Sacred Space Downtown Orlando Milk District
1 bedroom, 1 queen bed, 1 bathroom
6–11 Aug
5.0 out of 5 average rating, 266 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
26–31 Jul
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
17–22 Oct
4.98 out of 5 average rating, 44 reviews
Superhost
Home in Kissimmee
5 BD/ 4 BA/ Terra Verde (4669 GB)
5 bedrooms, 7 beds, 4 bathrooms
30 Jul – 4 Aug
Superhost
Home in Clermont
2026 NEW! Stunning 09 Bedroom at Windsor Cay
9 bedrooms, 12 beds, 6 bathrooms
28 Aug – 2 Sept
New place to stay