Vacation rentals in Winter Park, FL

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Travel insights for vacation rentals in Winter Park

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What is the cheapest day to stay in a vacation rental in Winter Park?

The cheapest day to stay in Winter Park is Monday ($111). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $580.
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Other accommodations in Winter Park

Find the perfect vacation rental for your stay in Winter Park, FL. There are 93 hotels in Winter Park, FL and price data was last updated on August 14, 2025. The average price for a hotel in Winter Park, FL is .
The Alfond Inn
The Alfond Inn

The Alfond Inn

300 East New England Avenue, Winter Park, FL, United States
0.6 mi from city centre
Free Wi-Fi
$299
Avg. per night
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Where to stay in Winter Park

Explore different neighborhoods and areas within Winter Park, FL to find the perfect location for your stay. Map data was last updated on August 14, 2025.
Navigate to the areas in Winter Park you plan to visit to find vacation rentals that are close by. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

Facts about staying in Winter Park, FL

Find useful tips and insights about staying in Winter Park to help you make the most of your experience. FAQs were last updated on August 14, 2025.

  • How much does a vacation rental in Winter Park cost?

    $323 per night is how much a vacation rental in Winter Park costs, on average. $29 per night was the cheapest price recently found by our users, though anything for $308 per night or less is a good deal. Keep in mind that Winter Park vacation rental prices fluctuate throughout the year: the most expensive month to book is November, and the cheapest time to book is July.

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