Search results; Over 1,000 places in Winter Park

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Guest favorite
Cottage in Winter Park
Winter Park Pearl 6 min drive to historic Park Ave
2 beds
Jul 15 – 20
R14,280 ZAR for 5 nights
4.94 out of 5 average rating, 405 reviews
Superhost
Home in Winter Park
Cozy home 5min to Park Ave and Downtown Orlando
3 beds
Aug 24 – 29
R11,382 ZAR for 5 nights
4.87 out of 5 average rating, 23 reviews
Top guest favorite
Home in Winter Park
10 min to Winter Park, Games, Gym, King bd, Coffee
Free cancellation
Jul 26 – 31
R14,908 ZAR for 5 nights
5.0 out of 5 average rating, 12 reviews
Top guest favorite
Bungalow in Orlando
Cozy Cottage in College Park.
Free cancellation
Aug 4 – 9
R10,755 ZAR for 5 nights
4.98 out of 5 average rating, 107 reviews
Guest favorite
Home in Casselberry
Sunset Lake Retreat
Free cancellation
Jul 20 – 25
R22,682 ZAR for 5 nights
4.98 out of 5 average rating, 50 reviews
Top guest favorite
Guesthouse in Orlando
Location, Location, Location!
Free cancellation
Aug 10 – 15
R11,501 ZAR for 5 nights
4.99 out of 5 average rating, 70 reviews
Room in Winter Park
Stay with Wendy & The TeamBusiness owner,
Cozy & Spacious Master Ensuite w/ Private Entry
Jul 15 – 20
R7,995 ZAR for 5 nights
New place to stay
Top guest favorite
Room in Winter Park
Stay with AdamAerospace engineer,
Pura Vida Home 1
Nov 26 – Dec 1
R6,070 ZAR for 5 nights
4.93 out of 5 average rating, 300 reviews
Superhost
Home in Winter Park
Cheerful and stylish 2-bedroom with parking
3 beds
Jul 17 – 22
R19,700 ZAR for 5 nights
4.95 out of 5 average rating, 19 reviews
Superhost
Condo in Winter Park
Lovely Winter Park Home close to Hospitals !
Free cancellation
Aug 30 – Sep 4
R14,269 ZAR for 5 nights
4.82 out of 5 average rating, 102 reviews
Guest favorite
Home in Orlando
Charming Bungalow in Winter Park
Free cancellation
Aug 2 – 7
R18,617 ZAR for 5 nights
4.98 out of 5 average rating, 48 reviews
Camper/RV in Winter Park
Easy Stay Rv Suite
5 beds
Jul 24 – 29
R5,648 ZAR for 5 nights
New place to stay
Top guest favorite
Guesthouse in Orlando
Baldwin Park Guest House
Free cancellation
Jul 20 – 25
R10,436 ZAR for 5 nights
4.99 out of 5 average rating, 124 reviews
Guest favorite
Room in Orlando
Stay with RyanHosting for 7 years,
Peaceful and cozy one-bedroom near downtown
Aug 5 – 10
R4,153 ZAR for 5 nights
4.9 out of 5 average rating, 292 reviews
Guest favorite
Home in Winter Park
Charming home @wp. Patio +Gazebo. close to highwys
6 beds
Jul 20 – 25
R12,246 ZAR for 5 nights
4.89 out of 5 average rating, 92 reviews
Top guest favorite
Tiny home in Orlando
The Little Treehouse 2 at Country Club of Orlando
Free cancellation
Nov 16 – 21
R12,757 ZAR for 5 nights
4.97 out of 5 average rating, 770 reviews
Top guest favorite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 queen bed
Jul 20 – 25
R8,647 ZAR for 5 nights
4.98 out of 5 average rating, 399 reviews
Top guest favorite
Tiny home in Orlando
Shipping Container Home- College Park Neighborhood
Free cancellation
Jul 26 – 31
R15,121 ZAR for 5 nights
4.96 out of 5 average rating, 150 reviews