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Holiday rentals in Winter Park, Florida

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Travel insights for holiday rentals in Winter Park

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

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

The cheapest day to stay in Winter Park is Monday ($215). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $404.

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Other accommodations in Winter Park, FL

Find the perfect holiday rental for your stay in Winter Park, FL. There are 76 hotels in Winter Park, FL and price data was last updated on 29 July 2026. The average price for a hotel in Winter Park, FL is .
Winter Park charm
Winter Park charm

Winter Park charm

1201 N Denning Drive, Winter Park, FL, United States
2.4 km from city centre
Free Wi-Fi
Parking
$136
Avg. per night
View Deal
The Alfond Inn
The Alfond Inn

The Alfond Inn

300 East New England Avenue, Winter Park, FL, United States
0.9 km from city centre
Free Wi-Fi
$408
Avg. per night
View Deal
Park Plaza Hotel
Park Plaza Hotel

Park Plaza Hotel

307 South Park Avenue, Winter Park, FL, United States
1.2 km from city centre
Free Wi-Fi
$293
Avg. per night
View Deal

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 29 July 2026.
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 29 July 2026.

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

    $270 per night is how much a holiday rental in Winter Park costs, on average. $69 per night was the cheapest price recently found by our users, though anything for $257 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 July, and the cheapest time to book is February.

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