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: 87
$245/night
Cute bungalow minutes walk from Park Ave.
2 beds
2 baths
4 guests
Average Price:
$267
8% Cheaper
than normal
AirDNA Score: 86
$200/night
AirDNA Score: 80
$189/night
Charming cottage in the heart of Winter Park
2 beds
2 baths
4 guests
Average Price:
$247
23% Cheaper
than normal
AirDNA Score: 76
$101/night
Winter Park Pearl 6 min drive to historic Park Ave
3 beds
1.5 baths
4 guests
Average Price:
$173
42% Cheaper
than normal
AirDNA Score: 73
$229/night
Stroll to Park Avenue from Vintage Lake-View home
2 beds
2 baths
6 guests
Average Price:
$318
28% Cheaper
than normal
AirDNA Score: 71
$87/night
3 bedroom Family Home on Quiet Historic Street
3 beds
1 bath
6 guests
Average Price:
$241
64% Cheaper
than normal
AirDNA Score: 71
$155/night
Private & Secluded Poolside Cottage in Winter Park
1 bed
1 bath
4 guests
Average Price:
$148
5% More
than normal
AirDNA Score: 68
$200/night
Greatest Location in Winter Park! (2)
2 beds
2 baths
5 guests
Average Price:
$270
26% Cheaper
than normal
AirDNA Score: 66
$75/night
Condo 1100sq ft close to all the fun and excitemen
2 beds
2 baths
4 guests
Average Price:
$91
18% Cheaper
than normal
AirDNA Score: 66
$89/night
AirDNA Score: 64
$92/night
Butterfly Garden Cozy Cottage -Winter Park Orlando
1 bed
1 bath
2 guests
Average Price:
$98
6% Cheaper
than normal
AirDNA Score: 64
$95/night
AirDNA Score: 64
$250/night
Historic Winter Park off Park Ave
2 beds
1 bath
4 guests
Average Price:
$265
6% Cheaper
than normal
AirDNA Score: 64
$85/night
Comfortable & Spacious 2/1 Condo in Winter Park!!
2 beds
1 bath
4 guests
Average Price:
$99
14% Cheaper
than normal
AirDNA Score: 63
$92/night
Orlando / Winter park condo with large space clean
2 beds
2 baths
4 guests
Average Price:
$89
3% More
than normal
AirDNA Score: 63
$199/night
Luxury Downtown Winter Park Guesthouse
1 bed
1 bath
2 guests
Average Price:
$210
5% Cheaper
than normal
AirDNA Score: 53
$209/night
Charming, Spanish Cottage in heart of Winter Park
2 beds
2 baths
4 guests
Average Price:
$272
23% Cheaper
than normal
AirDNA Score: 50
$55/night
Remote Work Getaway in Winter Park, Florida
1 bed
1 bath
2 guests
Average Price:
$61
10% Cheaper
than normal
AirDNA Score: 49
$315/night
On Campus without being on Campus Rollins College!
2 beds
2 baths
5 guests
Average Price:
$330
5% Cheaper
than normal
AirDNA Score: 48
$325/night
As close as you can stay to Rollins College!
2 beds
2 baths
5 guests
Average Price:
$313
4% More
than normal
AirDNA Score: 46
$190/night
#1 - Enjoy 3 Bedroom 2 Bath home Centrally Located
3 beds
2 baths
6 guests
Average Price:
$208
9% Cheaper
than normal
AirDNA Score: 39
$62/night
***VILLA LUCHIA*** WINTER PARK, FLORIDA
1 bed
1 bath
2 guests
Average Price:
$72
14% Cheaper
than normal
AirDNA Score: 37
$89/night
Private Winter Park Apartment, Pool, Bike Trails!
1 bed
1 bath
3 guests
Average Price:
$94
5% Cheaper
than normal
AirDNA Score: 35
$299/night
Welcome anyone visiting Rollins College!
2 beds
2 baths
5 guests
Average Price:
$301
1% Cheaper
than normal
AirDNA Score: 29
$997/night
Lakeside: exclusive ''olde Winter Park'' (32789)
4 beds
4 baths
8 guests
Average Price:
$884
13% More
than normal