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

The English Shed

1 bed
1 bath
3 guests
Average Price:  
$237
16% Cheaper
than normal
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

Winter Park Bungalow

1 bed
1 bath
2 guests
Average Price:  
$79
13% More
than normal
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

Joe''s Grotto

1 bed
1 bath
2 guests
Average Price:  
$104
9% Cheaper
than normal
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