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Vacation rentals in Winter Park, FL

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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 May ($82). Conversely, the most expensive month to stay in Winter Park is June ($308).

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

The cheapest day to stay in Winter Park is Saturday ($85). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $282.

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Other accommodations in Winter Park

The Alfond Inn
The Alfond Inn

The Alfond Inn

300 East New England Avenue, Winter Park, FL, United States
0.6 mi from city centre
Free Wi-Fi
$291
Avg. per night
View Deal
Park Plaza Hotel
Park Plaza Hotel

Park Plaza Hotel

307 South Park Avenue, Winter Park, FL, United States
0.8 mi from city centre
Free Wi-Fi
$181
Avg. per night
View Deal

Where to stay in Winter Park

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

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

    $170 per night is how much a vacation rental in Winter Park costs, on average. $29 per night was the cheapest price recently found by our users, though anything for $158 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 February, and the cheapest time to book is August.

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