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Vacation 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 month to book a vacation rental in Winter Haven?

The cheapest month to book a vacation rental in Winter Haven is September ($43). Conversely, the most expensive month to stay in Winter Haven is May ($289).

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

The cheapest day to stay in Winter Haven is Tuesday ($113). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $239.

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 $119 per night.
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Other accommodations in Winter Haven

Find the perfect holiday rental for your stay in Winter Haven. There are 213 hotels in Winter Haven and price data was last updated on 14 September 2025. The average price for a hotel in Winter Haven is $138/night.
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
$72
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
$86
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
$86
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 14 September 2025.
Utilize the map to find properties close to the Winter Haven 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 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 14 September 2025.

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

    The average cost for a holiday rental in Winter Haven is $139/night. A good holiday rental deal in Winter Haven would be for $126/night or less. The cheapest rental deal found recently by our users was $24/night. If you’re flexible with your travel dates, then try to avoid booking May, the most expensive month of the year. Booking September is the cheapest month to book a holiday rental in Winter Haven.

  • Are there any Motel holiday rentals in Winter Haven?

    Yes, there are 13 Motel holiday rentals in Winter Haven. According to our data, Howard Johnson by Wyndham Winter Haven FL is currently the most popular Motel rental in the city.

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