Best price vacation rentals in Winter Springs, FL, USA • 150 Listings
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Winter Springs, 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 (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 (72)
Fully Renovated "Old Florida" Apartment
Up to 2 guests
Airbnb$100
Vrbo$100
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 (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)
Edgewater lake house Sanford/Orlando near SFB
Up to 7 guests
Airbnb$155
Vrbo$158
Average Nightly Rate
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5.0 (16)
Peaceful ranch life! Come stay amongst the horses in your back yard
Up to 6 guests
Airbnb$190
Vrbo$190
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 (50)
Downtown Paradise
Up to 10 guests
Airbnb$226
Vrbo$267
Average Nightly Rate
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5.0 (25)
Country Quiet | 1.05 Protected Acres | All-New Interior | Gas Grill & Firepit
Up to 5 guests
Vrbo$108
Airbnb$128
Average Nightly Rate
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5.0 (11)
The Lux At Lake Mary
Up to 5 guests
Airbnb$145
Vrbo$152
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 (77)
The Ivy Cottage@Park Place Inn
Up to 4 guests
Airbnb$130
Vrbo$133
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 (39)
The Palm Cottage @ Downtown Sanford
Up to 4 guests
Airbnb$111
Vrbo$125
Average Nightly Rate
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5.0 (34)
Bungalow in Historic Sanford walk to Eatery & Bars
Up to 5 guests
Airbnb$111
Vrbo$125
Average Nightly Rate
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5.0 (196)
The Galaxy - A tiny house that is out of this world!
Up to 4 guests
Airbnb$98
Vrbo$99
Average Nightly Rate
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5.0 (158)
East Orlando Vacation Home Rental At A Great Value!
Up to 10 guests
Airbnb$164
Vrbo$169
Average Nightly Rate
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5.0 (237)
Where Luxury meets affordability
Up to 8 guests
Airbnb$166
Vrbo$175
Average Nightly Rate
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5.0 (283)
The Retreat - Adorable tiny home steps from the lake!
Up to 4 guests
Airbnb$89
Vrbo$96
Average Nightly Rate
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5.0 (69)
Magnificent Lakefront House • Swim/Fish/Relax • EV Charger
Up to 12 guests
Airbnb$572
Vrbo$572
Average Nightly Rate
  1. United States
  2. Florida
  3. Winter Springs Vacation Rental Price Comparison

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

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