The Best Airbnb Deals in
Winter Park, Florida
Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Winter Park, Florida. Enter your travel dates to find the best deals!
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AirDNA Score: 86
$95/night
winter park rollins area priv. garden cabana style
1 bed
1 bath
3 guests
Average Price:
$140
32% Cheaper
than normal
AirDNA Score: 86
$125/night
Lakefront Apartment W/ Pool & Spa -Great Location!
1 bed
1 bath
4 guests
Average Price:
$116
8% More
than normal
AirDNA Score: 79
$115/night
Get a Little Glam in a Retro Palm Beach-Style Boudoir
1 bed
1 bath
2 guests
Average Price:
$146
21% Cheaper
than normal
AirDNA Score: 76
$150/night
Winter Park Pearl 6 min drive to historic Park Ave
3 beds
1.5 baths
4 guests
Average Price:
$201
25% Cheaper
than normal
AirDNA Score: 75
$395/night
A Rare Jewel in the heart of Winter park. Can walk
3 beds
2 baths
6 guests
Average Price:
$427
7% Cheaper
than normal
AirDNA Score: 73
$110/night
AirDNA Score: 72
$89/night
Orlando Winter Park Guest Room 0.5 mi to Hospital
1 bed
1 bath
1 guest
Average Price:
$104
14% Cheaper
than normal
AirDNA Score: 71
$125/night
Private & Secluded Poolside Cottage in Winter Park
1 bed
1 bath
4 guests
Average Price:
$189
34% Cheaper
than normal
AirDNA Score: 68
$375/night
Greatest Location in Winter Park! (2)
2 beds
2 baths
5 guests
Average Price:
$332
13% More
than normal
AirDNA Score: 64
$69/night
Butterfly Garden Cozy Cottage -Winter Park Orlando
1 bed
1 bath
2 guests
Average Price:
$92
25% Cheaper
than normal
AirDNA Score: 64
$89/night
Quaint Key West Pool Home
1 bed
1 bath
2 guests
Average Price:
$156
43% Cheaper
than normal
AirDNA Score: 64
$120/night
AirDNA Score: 60
$118/night
𝕎𝕚𝕟𝕥𝕖𝕣 ℙ𝕒𝕣𝕜 𝔹𝕒𝕞𝕓𝕠𝕠 𝕃𝕠𝕗𝕥
1 bed
1 bath
4 guests
Average Price:
$94
26% More
than normal
AirDNA Score: 58
$499/night
Luxury Home in Downtown Winter Park
2 beds
2 baths
4 guests
Average Price:
$554
10% Cheaper
than normal
AirDNA Score: 53
$145/night
Modern, Quiet & Cozy - Entire house /Winter park
2 beds
2 baths
4 guests
Average Price:
$170
15% Cheaper
than normal
AirDNA Score: 49
$345/night
On Campus without being on Campus Rollins College!
2 beds
2 baths
5 guests
Average Price:
$344
0% Cheaper
than normal
AirDNA Score: 46
$205/night
No Cleaning fee - Winter Park 3br 2bath home
3 beds
2 baths
6 guests
Average Price:
$229
10% Cheaper
than normal
AirDNA Score: 45
$159/night
WeLive Winter Park / Spacious Enclave W/ Patio!
4 beds
1 bath
10 guests
Average Price:
$156
2% More
than normal
AirDNA Score: 43
$155/night
Walk to Park Ave & The WP Village!
3 beds
2.5 baths
6 guests
Average Price:
$203
24% Cheaper
than normal
AirDNA Score: 43
$69/night
Private entrance/pool/bike trails!
1 bed
1 bath
2 guests
Average Price:
$74
7% Cheaper
than normal
AirDNA Score: 37
$89/night
Private Winter Park Apartment, Pool, Bike Trails!
1 bed
1 bath
3 guests
Average Price:
$95
6% Cheaper
than normal
AirDNA Score: 33
$180/night
Comfy 3 Bedrooms - 2 Bathrooms home with pool.
3 beds
2 baths
8 guests
Average Price:
$209
14% Cheaper
than normal
AirDNA Score: 23
$298/night
Large, Beautiful Winter Park Home Available now!
4 beds
3 baths
8 guests
Average Price:
$370
19% Cheaper
than normal