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

Chateau Bungalow

3 beds
1 bath
4 guests
Average Price:  
$108
12% Cheaper
than normal
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

Balfour Palms

studio
1 bath
2 guests
Average Price:  
$95
21% Cheaper
than normal
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

Joe''s Grotto

1 bed
1 bath
2 guests
Average Price:  
$105
14% More
than normal
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