Best price vacation rentals in Winter Park, FL, USA • 150 Listings
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Winter Park, FL, USA Vacation Rentals | 

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5.0 (200)
The Blue Heron - Lakefront Getaway
Up to 4 guests
Airbnb$89
Vrbo$101
Average Nightly Rate
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5.0 (148)
Just 3 blocks to Park Ave shops / restaurants, 2 from Winter Park Village!
Up to 6 guests
Airbnb$171
Vrbo$189
Average Nightly Rate
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5.0 (389)
The Ritz - Just because it’s a tiny house, doesn't mean you have to skimp on ...
Up to 5 guests
Airbnb$103
Vrbo$115
Average Nightly Rate
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5.0 (369)
The Cottage - Quaint tiny home filled with charm!
Up to 3 guests
Airbnb$89
Vrbo$120
Average Nightly Rate
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5.0 (10)
Elegant College Park Cottage w/ Patio & Gas Grill!
Up to 4 guests
Vrbo$104
Airbnb$108
Average Nightly Rate
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5.0 (201)
Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths
Up to 4 guests
Airbnb$130
Vrbo$130
Average Nightly Rate
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5.0 (122)
Cozy comfort in the heart of the winter park!
Up to 4 guests
Vrbo$109
Airbnb$114
Average Nightly Rate

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5.0 (351)
The Little Treehouse 2 at The Country Club of Orlando
Up to 2 guests
Vrbo$113
Airbnb$123
Average Nightly Rate
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5.0 (363)
The Venice - Trendy tiny home with panoramic views of beautiful Lake Fairview!
Up to 3 guests
Airbnb$103
Vrbo$113
Average Nightly Rate

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5.0 (62)
Mid-Century Modern Gem Near Downtown/Winter Park/Baldwin Park
Up to 6 guests
Airbnb$158
Vrbo$170
Average Nightly Rate
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5.0 (436)
The Little Tree House at the Country Club of Orlando
Up to 2 guests
Vrbo$113
Airbnb$123
Average Nightly Rate
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5.0 (38)
Updated Historic bungalow in Lake Eola Heights
Up to 4 guests
Vrbo$134
Airbnb$141
Average Nightly Rate
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5.0 (217)
The Universal - Stylish tiny home perfect for a family vacation
Up to 4 guests
Airbnb$99
Vrbo$112
Average Nightly Rate
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5.0 (46)
Private & Quiet Apartment in East Orlando, Near 408/417
Up to 2 guests
Vrbo$67
Airbnb$67
Average Nightly Rate
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5.0 (70)
Beautiful Peaceful fenced yard home !
Up to 10 guests
Airbnb$248
Vrbo$277
Average Nightly Rate
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5.0 (3)
Sonder Wellborn | Queen Room
Up to 2 guests
Vrbo$155
Airbnb$164
Average Nightly Rate
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5.0 (132)
First-Class Crash Pad!
Up to 2 guests
Airbnb$68
Vrbo$68
Average Nightly Rate
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5.0 (19)
Modern 3/2.5 DT Home - King Bed- Patios - Long Stays - WiFi
Up to 8 guests
Airbnb$340
Vrbo$368
Average Nightly Rate
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5.0 (10)
Peaceful, Highrise Loft
Up to 5 guests
Airbnb$124
Vrbo
Average Nightly Rate
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5.0 (7)
Fully renovated 1905 Victorian
Up to 6 guests
Airbnb$179
Vrbo$187
Average Nightly Rate
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5.0 (6)
Lovely 2/2 Apartment in Downtown Orlando with parking
Up to 4 guests
Vrbo$195
Airbnb$206
Average Nightly Rate
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5.0 (38)
Large beautiful very comfortable one bedroom on small lake
Up to 2 guests
Airbnb$165
Vrbo$168
Average Nightly Rate
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5.0 (221)
The View - Waterfront tiny home with incredible panoramic views
Up to 4 guests
Airbnb$109
Vrbo$113
Average Nightly Rate
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5.0 (148)
WeLive Winter Park / Spacious Enclave W/ Patio!
Up to 10 guests
Vrbo$182
Airbnb$190
Average Nightly Rate
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5.0 (87)
Luxurious 2/2 Penthouse in downtown Orlando with a billiard room&oversized patio
Up to 4 guests
Vrbo$215
Airbnb$231
Average Nightly Rate
  1. United States
  2. Florida
  3. Winter Park Vacation Rental Price Comparison

Compare Airbnb vs. Booking.com vs. Vrbo prices for vacation rentals in Winter Park, FL, USA

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