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Vacation rentals in Winter Haven

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Travel insights for vacation rentals in Winter Haven

Use our HotelsCombined data-powered tips to help you find your next vacation rental in Winter Haven.

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 $243.

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 vacation rental for your stay in Winter Haven. There are 213 hotels in Winter Haven and price data was last updated on septiembre 11, 2025. The average price for a hotel in Winter Haven is $138/night.
Lake Ida Beach Resort
Lake Ida Beach Resort

Lake Ida Beach Resort

2524 Lake Alfred Road, Winter Haven, FL, United States
1.9 mi from city centre
Free Wi-Fi
Air Conditioning
$75
Avg. per night
View Deal
LEGOLAND Florida Resort
LEGOLAND Florida Resort

LEGOLAND Florida Resort

1 Legoland Way, Winter Haven, FL, United States
3.2 mi from city centre
Free Wi-Fi
$269
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
2.2 mi from city centre
Free Wi-Fi
Parking
$88
Avg. per night
View Deal
Economy Suites
Economy Suites

Economy Suites

1901 Cypress Gardens Boulevard, Winter Haven, FL, United States
2.3 mi 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
0.3 mi 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
0.9 mi from city centre
Free Wi-Fi
Parking
$86
Avg. per night
View Deal

Where to stay in Winter Haven

Explore different neighborhoods and areas within Winter Haven to find the perfect location for your stay. Map data was last updated on septiembre 11, 2025.
Scroll to and zoom in on the areas in Winter Haven you plan on visiting to find nearby properties. 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 septiembre 11, 2025.

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

    $139 per night is how much a vacation rental in Winter Haven costs, on average. $24 per night was the cheapest price recently found by our users, though anything for $126 per night or less is a good deal. Keep in mind that Winter Haven vacation 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 vacation rentals in Winter Haven?

    At the moment, there are 13 properties listed as a Motel vacation 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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