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Holiday hires 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 month to book a vacation rental in Winter Haven?

The cheapest month to book a vacation rental in Winter Haven is October ($97). Conversely, the most expensive month to stay in Winter Haven is May ($446).

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

The cheapest day to stay in Winter Haven is Tuesday ($166). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $422.
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Other accommodations in Winter Haven

Find the perfect holiday rental for your stay in Winter Haven. There are 162 hotels in Winter Haven and price data was last updated on 23 10月 2025. The average price for a hotel in Winter Haven is $222/night.
Lake Ida Beach Resort
Lake Ida Beach Resort

Lake Ida Beach Resort

2524 Lake Alfred Road, Winter Haven, FL, United States
3.1 km from city centre
Free Wi-Fi
Air conditioning
$117
Avg. per night
View Deal
LEGOLAND Florida Resort
LEGOLAND Florida Resort

LEGOLAND Florida Resort

1 Legoland Way, Winter Haven, FL, United States
5.2 km from city centre
Free Wi-Fi
$384
Avg. per night
View Deal
Economy Suites
Economy Suites

Economy Suites

1901 Cypress Gardens Boulevard, Winter Haven, FL, United States
3.6 km from city centre
Free Wi-Fi
Parking
$113
Avg. per night
View Deal
Budget Inn Of Winter Haven
Budget Inn Of Winter Haven

Budget Inn Of Winter Haven

401 6th Street Hwy 17n, Winter Haven, FL, United States
0.4 km from city centre
Free Wi-Fi
Parking
Air conditioning
$132
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
$132
Avg. per night
View Deal
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
$147
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 23 10月 2025.
Use the map to find holiday rentals in Winter Haven that are close to the points of interest you'll be frequenting. Clicking a property's name will unlock more information and allow you to book that particular 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 23 10月 2025.

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

    $223 per night is how much a holiday rental in Winter Haven costs, on average. $32 per night was the cheapest price recently found by our users, though anything for $194 per night or less is a good deal. Keep in mind that Winter Haven holiday rental prices fluctuate throughout the year: the most expensive month to book is May, and the cheapest time to book is November.

  • Are there any Motel holiday rentals in Winter Haven?

    If you’re looking to book a Motel holiday rental in Winter Haven, then you have 13 to choose from. We recommend looking at Howard Johnson by Wyndham Winter Haven FL as it’s currently the most popular Motel rental among our users.

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