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Holiday rentals in Winter Haven

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Travel insights for holiday rentals in Winter Haven

Use these up-to-date, data-driven insights about booking a holiday rental in Winter Haven including ideal times to book, pricing trends, and more.

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

The cheapest day to stay in Winter Haven is Thursday ($172). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $474.
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Other accommodations in Winter Haven

Find the perfect holiday rental for your stay in Winter Haven. There are 159 hotels in Winter Haven and price data was last updated on 9 December 2025. The average price for a hotel in Winter Haven is .
Lake Roy Beach Inn - Winter Haven
Lake Roy Beach Inn - Winter Haven

Lake Roy Beach Inn - Winter Haven

1823 Cypress Gardens Boulevard, Winter Haven, FL, United States
3.6 km from city centre
Free Wi-Fi
Parking
$171
Avg. per night
View Deal
Budget Inn Winter Haven
Budget Inn Winter Haven

Budget Inn Winter Haven

401 6th Street Hwy 17n, Winter Haven, FL, United States
0.4 km from city centre
Free Wi-Fi
Parking
Air conditioning
$149
Avg. per night
View Deal
Howard Johnson by Wyndham Winter Haven FL
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

1300 3rd Street Southwest, Winter Haven, FL, United States
1.5 km from city centre
Free Wi-Fi
Parking
$126
Avg. per night
View Deal

Where to stay in Winter Haven

Explore different neighbourhoods and areas within Winter Haven to find the perfect location for your stay. Map data was last updated on 9 December 2025.
Navigate to the areas in Winter Haven you plan to visit to find holiday rentals that are close by. As an added benefit, users can click a holiday rental they're interesting in to find helpful information and deals for that holiday rental.

Facts about staying in Winter Haven

Find useful tips and insights about staying in Winter Haven to help you make the most of your experience. FAQs were last updated on 9 December 2025.

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

    $198/night is a typical cost for a holiday rental in Winter Haven throughout the year. Rental prices do vary though, and you’ll find that June is the most expensive month to book, and October is the cheapest month to book. HotelsCombined users recently found Winter Haven holiday rentals for as low as $42/night. In general, any Winter Haven rental for $192 or less is a good deal.

  • Are there any Motel holiday rentals in Winter Haven?

    At the moment, there are 13 properties listed as a Motel holiday rental in Winter Haven. A popular Motel in Winter Haven amongst our users is Howard Johnson by Wyndham Winter Haven FL.

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