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Holiday Rentals in Winter Park, FL

Search and compare Winter Park, FL vacation rentals from hundreds of travel sites and save.

Winter Park, FL, United States
21 May — 22 May2
Winter Park, FL, United States
Tue 21/5
Wed 22/5
...and more

Tips for booking holiday rentals in Winter Park, FL

Gain useful insights and advice for booking the perfect stay in Winter Park, FL. Price data is based on averages over the past 12 months and was last updated on 14 May 2024.
Cheapest month:September
Most expensive month:April
Average price in Winter Park:$279/night
Cheapest price found:$133/night
Cheapest day:Tuesday
Most expensive day:Friday
$192 - $774
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
$137 - $843
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Where to stay in Winter Park, FL

Explore different neighbourhoods and areas within Winter Park to find the perfect location for your stay. Map data was last updated on 14 May 2024.
Utilise the map to find properties close to the Winter Park area(s) or attractions you plan on visiting. Users can click on a holiday rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

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 14 May 2024.

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

    $280 per night is how much a holiday rental in Winter Park costs, on average. $134 per night was the cheapest price recently found by our users, though anything for $266 per night or less is a good deal. Keep in mind that Winter Park holiday rental prices fluctuate throughout the year: the most expensive month to book is April, and the cheapest time to book is March.

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

    Florida Center is the best part of the city to stay in if you’re looking for a holiday rental in Winter Park. The Westgate Palace a Two Bedroom Condo Resort is our most popular holiday rental in this neighbourhood. While there are other neighbourhoods throughout Winter Park, 96% of HotelsCombined users searched for rentals in Florida Center in the past 12 months, making it a popular choice.

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