Search results; Over 1,000 homes in Winter Park

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Superhost
Home in Winter Park
Tranquil Oasis: 4BR Pool Home
8 guests4 bedrooms6 beds2 baths
Aug 23 – 28
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Aug 23 – 28
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R19,647 ZAR for 5 nights

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Top guest favorite
Room in Winter Park
Stay with Maria
Top Floor French Style Studio.
Aug 4 – 9
R7,850 ZAR for 5 nights
4.99 out of 5 average rating, 105 reviews
Top guest favorite
Guest suite in Eatonville
Private entrance/bathroom 10 min from DT Orlando
Free cancellation
Aug 1 – 6
R7,501 ZAR for 5 nights
4.98 out of 5 average rating, 173 reviews
Top guest favorite
Room in Winter Park
Stay with NathanRetail general mngr,
CrowAsis Citrus Room - Queen Size Bed
Aug 12 – 17
R7,959 ZAR for 5 nights
5.0 out of 5 average rating, 156 reviews
Top guest favorite
Tiny home in Orlando
Rustic Chic Tiny house @College/Winter Pk. Sleep 4
3 beds
Aug 3 – 8
R11,263 ZAR for 5 nights
5.0 out of 5 average rating, 47 reviews
Superhost
Home in Orlando
Vibrant Modular Home @Lk Fairview near Hospitals
5 beds
Aug 10 – 15
R9,126 ZAR for 5 nights
5.0 out of 5 average rating, 5 reviews
Top guest favorite
Home in Maitland
Florida Poolside Paradise a Great Place to Unwind!
4 beds
Aug 11 – 16
R29,897 ZAR for 5 nights
4.99 out of 5 average rating, 81 reviews
Guest favorite
Guest suite in Orlando
Private Guest unit W/Tropical Views!
Free cancellation
Aug 1 – 6
R7,647 ZAR for 5 nights
4.93 out of 5 average rating, 176 reviews
Top guest favorite
Home in Casselberry
Wana Chill Spot *Pool *Spa *Bar *Ping Pong *BBQ
4 beds
Aug 16 – 21
R19,798 ZAR for 5 nights
5.0 out of 5 average rating, 11 reviews
Top guest favorite
Room in Orlando
Stay with Stephen
Private room with own entrance. Built in 2022.
Aug 1 – 6
R7,917 ZAR for 5 nights
4.97 out of 5 average rating, 109 reviews
Guest favorite
Loft in Orlando
UPSCALE LOFT SPACE CLOSE TO DOWNTOWN.
Free cancellation
Aug 2 – 7
R14,793 ZAR for 5 nights
4.92 out of 5 average rating, 895 reviews
Top guest favorite
Bungalow in Orlando
Cozy Cottage in College Park.
Free cancellation
Aug 4 – 9
R10,522 ZAR for 5 nights
4.98 out of 5 average rating, 108 reviews
Guest favorite
Home in Winter Park
Charming Retreat In Winter Park
4 beds
Aug 3 – 8
R21,230 ZAR for 5 nights
4.88 out of 5 average rating, 94 reviews
Guest suite in Orlando
Guest Apt near Baldwin Park. Kitchenette Laundry
Free cancellation
Aug 3 – 8
R8,334 ZAR for 5 nights
4.82 out of 5 average rating, 90 reviews
Guest favorite
Room in Orlando
Stay with DariusControls designer,
Saltlake Oasis
Jan 5 – 10
R3,726 ZAR for 5 nights
4.88 out of 5 average rating, 230 reviews
Top guest favorite
Home in Orlando
3BR Oasis DT ORL, Full Kitchen & Fenced Yard!
Free cancellation
Aug 3 – 8
R16,039 ZAR for 5 nights
5.0 out of 5 average rating, 16 reviews
Guest favorite
Loft in Orlando
Contemporary Loft Near Downtown
Free cancellation
Aug 4 – 9
R14,793 ZAR for 5 nights
4.92 out of 5 average rating, 586 reviews
Superhost
Guest suite in Orlando
Backyard Courtyard, Near Baldwin Lake & Dining
Free cancellation
Aug 4 – 9
R11,105 ZAR for 5 nights
4.75 out of 5 average rating, 28 reviews
Home in Winter Park
The Briarcliff
Free cancellation
Aug 8 – 13
R24,168 ZAR for 5 nights
5.0 out of 5 average rating, 4 reviews