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
$103/night

winter park rollins area priv. garden cabana style

1 bed
1 bath
3 guests
Average Price:  
$140
26% Cheaper
than normal
AirDNA Score: 79
$244/night

Signature Barbour House Apt With King Size Bed 203

2 beds
2 baths
4 guests
Average Price:  
$348
30% Cheaper
than normal
AirDNA Score: 75
$439/night

A Rare Jewel in the heart of Winter park. Can walk

3 beds
2 baths
6 guests
Average Price:  
$423
4% More
than normal
AirDNA Score: 71
$229/night

Historic Architecturally Distinctive Apartment 520

1 bed
1 bath
2 guests
Average Price:  
$210
9% More
than normal
AirDNA Score: 64
$120/night

Joe''s Grotto

1 bed
1 bath
3 guests
Average Price:  
$130
8% Cheaper
than normal
AirDNA Score: 61
$68/night

Spacious and Private in lovely Winter Park Orlando

1 bed
1 bath
4 guests
Average Price:  
$77
12% Cheaper
than normal
AirDNA Score: 58
$650/night

Luxury Home in Downtown Winter Park

2 beds
2 baths
4 guests
Average Price:  
$565
15% More
than normal
AirDNA Score: 53
$131/night

Modern, Quiet & Cozy - Entire house /Winter park

2 beds
2 baths
4 guests
Average Price:  
$160
18% Cheaper
than normal
AirDNA Score: 49
$328/night

On Campus without being on Campus Rollins College!

2 beds
2 baths
5 guests
Average Price:  
$367
11% Cheaper
than normal
AirDNA Score: 48
$345/night

As close as you can stay to Rollins College!

2 beds
2 baths
5 guests
Average Price:  
$355
3% Cheaper
than normal
AirDNA Score: 46
$206/night

Winter Park - 3br 2bath home

3 beds
2 baths
6 guests
Average Price:  
$228
10% Cheaper
than normal
AirDNA Score: 35
$328/night

Welcome anyone visiting Rollins College!

2 beds
2 baths
5 guests
Average Price:  
$363
10% Cheaper
than normal
AirDNA Score: 23
$293/night

Large, Beautiful Winter Park Home Available now!

4 beds
3 baths
8 guests
Average Price:  
$359
18% Cheaper
than normal
AirDNA Score: 14
$110/night

Absolutely Perfect Winter Park Location!

2 beds
1 bath
4 guests
Average Price:  
$113
3% Cheaper
than normal