Holiday rentals in Winter Park, Florida

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Travel insights for holiday rentals in Winter Park

Use these up-to-date, data-driven insights about booking a holiday 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 (S$ 182). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is S$ 953.
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Other accommodations in Winter Park, FL

Find the perfect holiday 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
S$ 384
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.
Scroll to and zoom in on the areas in Winter Park you plan on visiting to find nearby properties. Clicking a property's name will unlock more information and allow you to book that particular vacation rental.

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 holiday rental in Winter Park cost?

    On average, it costs S$ 414 per night for a Winter Park holiday rental, but S$ 395 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Winter Park was for S$ 37 per night. If you can, try to avoid booking your rental November (as this is the most expensive month). Booking July (the cheapest month) may end up saving you money.

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