How much does a holiday rental in Winter Park cost?

Winter Park holiday rentals are £195/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 holiday rental in Winter Park, and July is often the cheapest month to book. Recently, our users found rentals for £21/night - which is currently the cheapest price. Keep in mind that anything £195/night or less is still considered a good deal.

What part of Winter Park is best to stay in?

Consider staying in Downtown when looking for Winter Park holiday rentals. Downtown is the most popular neighbourhood in the city according to our users. In fact, out of all users who looked for holiday rentals in Winter Park in the past year, 67% of them searched for rentals in Downtown. If it’s available, we recommend staying at the Charming 2-bedroom apartment with AC and WiFi in enchanting Winter Park, a HotelsCombined favourite when it comes to holiday rentals in Winter Park’s Downtown neighbourhood.

Holiday rentals in Winter Park, Florida

Search and compare Winter Park, Florida holiday rentals from hundreds of travel sites on HotelsCombined and save.

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 28 1월 2026.

Whether you're visiting Winter Park for leisure or business, utilise the map to find holiday rentals close to your ideal location. As an added benefit, users can click a holiday rental they're interesting in to find helpful information and deals for that holiday 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 28 1월 2026.

How much does a holiday rental in Winter Park cost?

What part of Winter Park is best to stay in?

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