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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 September ($100). Conversely, the most expensive month to stay in Winter Haven is May ($668).

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

The cheapest day to stay in Winter Haven is Tuesday ($260). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $552.

How far ahead should you book a vacation rental in Winter Haven?

Save money by booking a vacation rental at least 7 days before your trip to Winter Haven. The lowest price found when booking 7 days ahead was $181 per night.
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Other accommodations in Winter Haven

Find the perfect holiday rental for your stay in Winter Haven. There are 214 hotels in Winter Haven and price data was last updated on 9 September 2025. The average price for a hotel in Winter Haven is $210/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
$115
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
$438
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 September 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 9 September 2025.

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

    $211 per night is how much a holiday rental in Winter Haven costs, on average. $37 per night was the cheapest price recently found by our users, though anything for $192 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 September.

  • 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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Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under $76 and Hotels Under $152. Discover hotel discounts now and make your hotel reservation today.