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Holiday rentals in Winter Park, Florida

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Cheapest holiday rentals in Winter Park, FL

Discover affordable stays in Winter Park, FL that provide a quality experience without breaking the bank. Hotels in Winter Park, FL can be found for as low as $109 per night. There is currently one property in Winter Park, FL that can be booked for this price. Orlando Lakefront Tiny Houses is one of the hotels that can be booked for the lowest price in Winter Park, FL. Price data was last updated on 1 May 2025
These are the lowest prices we've found on vacation rentals in Winter Park at the moment. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
Show all 76 holiday rentals
Orlando Lakefront Tiny Houses
Orlando Lakefront Tiny Houses

Orlando Lakefront Tiny Houses

Orlando, FL, United States
5.5 km from city centre
Air conditioning
$109
Avg. per night
View Deal

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 1 May 2025. The average price for a hotel in Winter Park, FL is .
Show all 76 stays
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
$294
Avg. per night
View Deal

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 1 May 2025.
Utilize the map to find properties close to the Winter Park area(s) or attractions you plan on visiting. More information on a given vacation rental can be accessed by clicking the vacation 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 1 May 2025.

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

    The average cost for a holiday rental in Winter Park is $218/night. A good holiday rental deal in Winter Park would be for $199/night or less. The cheapest rental deal found recently by our users was $48/night. If you’re flexible with your travel dates, then try to avoid booking February, the most expensive month of the year. Booking March is the cheapest month to book a holiday rental in Winter Park.

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