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Vacation rentals in Winter Park, FL

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Winter Park, United States
Apr 8 — Apr 92
...and more

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Travel insights for vacation rentals in Winter Park

Use our HotelsCombined data-powered tips to help you find your next vacation rental in Winter Park.

What is the cheapest month to book a vacation rental in Winter Park?

The cheapest month to book a vacation rental in Winter Park is November ($108). Conversely, the most expensive month to stay in Winter Park is February ($534).

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

The cheapest day to stay in Winter Park is Tuesday ($152). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $453.

Other accommodations in Winter Park, FL

Find the perfect vacation rental for your stay in Winter Park, FL. There are 76 hotels in Winter Park, FL and price data was last updated on April 1, 2025. The average price for a hotel in Winter Park, FL is $234/night.
Show all 76 stays
300 East New England Avenue, Winter Park, FL, United States
0.6 mi from city centre
Free Wi-Fi
$282
Avg. per night
307 South Park Avenue , Winter Park, FL, United States
0.8 mi from city centre
Free Wi-Fi
$179
Avg. per night

Where to stay in Winter Park, FL

Explore different neighborhoods and areas within Winter Park to find the perfect location for your stay. Map data was last updated on April 1, 2025.
Navigate to the areas in Winter Park you plan to visit to find vacation rentals that are close by. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

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 April 1, 2025.
  • How much does a vacation rental in Winter Park cost?

    $234 per night is how much a vacation rental in Winter Park costs, on average. $31 per night was the cheapest price recently found by our users, though anything for $220 per night or less is a good deal. Keep in mind that Winter Park vacation rental prices fluctuate throughout the year: the most expensive month to book is July, and the cheapest time to book is August.

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