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
$100/night
winter park rollins area priv. garden 1 mo. min.
studio
1 bath
3 guests
Average Price:
$145
31% Cheaper
than normal
AirDNA Score: 86
$110/night
Winter Park Charm (Close proximity to Park Ave)
2 beds
1 bath
4 guests
Average Price:
$135
19% Cheaper
than normal
AirDNA Score: 83
$95/night
AirDNA Score: 79
$150/night
Great Winter Park Location Walk 2 Park Ave/Rollins
2 beds
1 bath
4 guests
Average Price:
$159
6% Cheaper
than normal
AirDNA Score: 79
$350/night
Lounge on Blue Velvet Couches at a Charming Hideaway
4 beds
2 baths
8 guests
Average Price:
$389
10% Cheaper
than normal
AirDNA Score: 76
$120/night
Winter Park Pearl 6 min drive to historic Park Ave
3 beds
1.5 baths
4 guests
Average Price:
$192
37% 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:
$419
6% Cheaper
than normal
AirDNA Score: 71
$50/night
Turquoise Paradise: Tiny House & Garden
1 bed
1 bath
2 guests
Average Price:
$82
39% Cheaper
than normal
AirDNA Score: 71
$99/night
3 bedroom Family Home on Quiet Historic Street
3 beds
1 bath
6 guests
Average Price:
$188
47% Cheaper
than normal
AirDNA Score: 71
$75/night
AirDNA Score: 69
$118/night
Chic Lake & Poolside Retreat in Winter Park
2 beds
1 bath
3 guests
Average Price:
$132
11% Cheaper
than normal
AirDNA Score: 68
$290/night
Greatest Location in Winter Park! (2)
2 beds
2 baths
5 guests
Average Price:
$345
16% Cheaper
than normal
AirDNA Score: 64
$120/night
AirDNA Score: 63
$199/night
Luxury Downtown Winter Park Guesthouse
1 bed
1 bath
2 guests
Average Price:
$226
12% Cheaper
than normal
AirDNA Score: 53
$325/night
Relax on a private lake in Winter Park!
2 beds
2 baths
4 guests
Average Price:
$347
6% Cheaper
than normal
AirDNA Score: 48
$299/night
As close as you can stay to Rollins College!
2 beds
2 baths
5 guests
Average Price:
$337
11% Cheaper
than normal
AirDNA Score: 45
$60/night
Laid back & Private in lovely Winter Park Orlando
1 bed
1 bath
4 guests
Average Price:
$61
2% Cheaper
than normal
AirDNA Score: 44
$139/night
Executive Rental - Private Ranch Style Home
3 beds
2 baths
5 guests
Average Price:
$152
9% 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: 35
$345/night
Welcome anyone visiting Rollins College!
2 beds
2 baths
5 guests
Average Price:
$368
6% Cheaper
than normal