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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
27 May — 28 May2
Winter Park, FL, United States
Mon 27/5
Tue 28/5
...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 20 May 2024.
Cheapest month:September
Most expensive month:April
Average price in Winter Park:$301/night
Cheapest price found:$143/night
Cheapest day:Tuesday
Most expensive day:Friday
$207 - $833
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
$147 - $908
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 20 May 2024.
Use the map to find holiday rentals in Winter Park that are close to the points of interest you'll be frequenting. More information on a given holiday rental can be accessed by clicking the holiday rental's name within the map.

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 20 May 2024.

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

    $301/night is a typical cost for a holiday rental in Winter Park throughout the year. Rental prices do vary though, and you’ll find that April is the most expensive month to book, and March is the cheapest month to book. HotelsCombined users recently found Winter Park holiday rentals for as low as $144/night. In general, any Winter Park rental for $287 or less is a good deal.

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

    Florida Center is the most popular area of Winter Park to stay in. In the past year, 98% of HotelsCombined users looking for Winter Park holiday rentals searched within Florida Center. Based on user data, the Westgate Palace a Two Bedroom Condo Resort is one of the most popular holiday rentals in Florida Center.

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