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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Apartment in Winter Park
Winter Park Studio: On the River~ Walk Downtown!
Studio, 2 beds, 1 private bathroom
6–11 Jul
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4.98 out of 5 average rating, 421 reviews
Superhost
Home in Winter Park
Ramble Retreat I Downtown Winter Park w/Hot Tub
4 bedrooms, 7 beds, 4.5 bathrooms
11–16 Jul
New place to stay
Top guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds, 4 bathrooms
5–10 Jul
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Winter Park
Downtown WP Loft 21 - Rooftop HotTub - Great Views
3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Jul
4.88 out of 5 average rating, 32 reviews
Guest favourite
Apartment in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds, 1 bathroom
2–7 Jul
4.94 out of 5 average rating, 157 reviews
Home in Fraser
Hot Tub+Forest Chalet | Walk to Town | Sleeps 10
3 bedrooms, 6 beds, 3.5 bathrooms
1–6 Jul
Guest favourite
Apartment in Winter Park
Modern condo w/ hot tub & fireplace
3 bedrooms, 7 beds, 3 bathrooms
12–17 Jul
4.92 out of 5 average rating, 37 reviews
Guest favourite
Home in Winter Park
Winter Park Home | Hot Tub Sauna Walk to Downtown
4 bedrooms, 5 beds, 3.5 bathrooms
24–29 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Fraser
Spruce Ridge Villa 714H - Great Views - Bunk Room
3 bedrooms, 5 beds, 3 bathrooms
5–10 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Winter Park
Chateau Louise • Steps From Music In The Park
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Winter Park
Downtown WP Loft 106 - Huge Hot Tub - Great Views
3 bedrooms, 8 beds, 2 bathrooms
1–6 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Winter Park
The Best Location in Downtown Winter Park!
2 bedrooms, 5 beds, 3 bathrooms
5–10 Jul
4.96 out of 5 average rating, 107 reviews
Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds, 3 bathrooms
7–12 Aug
4.92 out of 5 average rating, 71 reviews
Guest favourite
Home in Winter Park
Downtown WP Loft 206 - Large Hot Tub - Great Views
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 15 reviews
Guest favourite
Apartment in Winter Park
Summer Escape • Riverfront Stay in WP
2 bedrooms, 4 beds, 3 bathrooms
4–9 Jul
4.89 out of 5 average rating, 9 reviews
Home in Winter Park
Summit Haus
5 bedrooms, 8 beds, 5.5 bathrooms
8–13 Jul
New place to stay
Top guest favourite
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 495 reviews
Guest favourite
Apartment in Winter Park
10 min to Resort! Amazing Views & Sauna!
3 bedrooms, 3 beds, 2 bathrooms
1–6 Jul
4.95 out of 5 average rating, 153 reviews
Guest favourite
Home in Winter Park
Downtown WP Condo 1409 - Hot Tub - Views - Firepit
2 bedrooms, 4 beds, 2 bathrooms
11–16 Jul
4.93 out of 5 average rating, 28 reviews