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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 (S$ 71). Conversely, the most expensive month to stay in Winter Haven is May (S$ 475).

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

The cheapest day to stay in Winter Haven is Tuesday (S$ 185). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is S$ 392.

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 S$ 152 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 S$ 177/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
S$ 97
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
S$ 330
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
S$ 112
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
S$ 92
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.
Navigate to the areas in Winter Haven you plan to visit to find vacation rentals that are close by. As an added benefit, users can click a vacation rental they're interesting in to find helpful information and deals for that vacation 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 14 September 2025.

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

    On average, it costs S$ 178 per night for a Winter Haven holiday rental, but S$ 162 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Winter Haven was for S$ 31 per night. If you can, try to avoid booking your rental May (as this is the most expensive month). Booking September (the cheapest month) may end up saving you money.

  • Are there any Motel holiday rentals in Winter Haven?

    There are 13 holiday rentals in Winter Haven that fall under the Motel category, the most popular is Howard Johnson by Wyndham Winter Haven FL.

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