Vacation rentals in Winter Park, FL

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Travel insights for vacation rentals in Winter Park

Use these up-to-date, data-driven insights about booking a vacation rental in Winter Park including ideal times to book, pricing trends, and more.

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

The cheapest day to stay in Winter Park is Monday (C$ 212). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is C$ 1,107.
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Other accommodations in Winter Park, FL

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 17 August 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
0.9 km from city centre
Free Wi-Fi
C$ 414
Avg. per night
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Where to stay in Winter Park

Explore different neighbourhoods and areas within Winter Park, FL to find the perfect location for your stay. Map data was last updated on 17 August 2025.
Whether you're visiting Winter Park for leisure or business, utilize the map to find vacation rentals close to your ideal location. You can find more information on a particular vacation rental within the map by clicking on its name.

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 17 August 2025.

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

    Winter Park vacation rentals are C$ 446/night on average. However, you may find that prices fluctuate depending on the time of year. For example, November is the most expensive month to book a vacation rental in Winter Park, and July is often the cheapest month to book. Recently, our users found rentals for C$ 40/night - which is currently the cheapest price. Keep in mind that anything C$ 426/night or less is still considered a good deal.

  • What part of Winter Park is best to stay in?

    Downtown is the best part of Winter Park to stay in based on our user data. Out of all our users who looked at Winter Park vacation rentals, 0% of them looked for stays in the Downtown neighbourhood in the last year. The Charming 2-bedroom apartment with AC and WiFi in enchanting Winter Park happens to be the most popular vacation rental in the Downtown neighbourhood of Winter Park.

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