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Holiday rentals in Winter Park, Florida

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Winter Park, United States
2 May — 3 May2
...and more

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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 $183 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 25 April 2025
For those on a budget, these are the cheapest holiday rentals available in Winter Park for the selected dates. Consider alternative dates if you're able to compare prices.
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
$183
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 25 April 2025. The average price for a hotel in Winter Park, FL is .
Show all 76 stays
Winter Park charm
Winter Park charm

Winter Park charm

1201 North Denning Drive, Winter Park, FL, United States
2.4 km from city centre
Free Wi-Fi
Parking
$293
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 25 April 2025.
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 25 April 2025.

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

    $377/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 February 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 $80/night. In general, any Winter Park rental for $332 or less is a good deal.

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