Winter Haven Holidays

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Top Flight + Hotel Deals in Winter Haven

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG
The Avalon Club
RumFish Beach at TradeWinds
Pelican Pointe Clearwater Beach Hotel
Landing Apartments near Sun City Center and Riverview

Things to do in and around Winter Haven

Winter Haven, Florida, is an ideal destination for families and adventure seekers alike, offering a variety of activities. Visitors can enjoy a delightful amusement park, explore a fascinating flight museum with its impressive aircraft collections, and indulge in shopping at local areas. For those seeking outdoor fun, there are also splendid golf courses and various activities to partake in, ensuring a memorable vacation experience.

Shopping

Havendale Plaza Shopping Center, located 11.3km from Winter Haven, offers a vibrant mix of business and entertainment. Southgate Shopping Center is 14.5km away, boasting a similar atmosphere. For a bit of a drive, Northgate Shopping Center is also nearby, providing delightful shopping options for all ages.

Recreation

Experience serenity at Sertoma Park, where you can unwind amidst nature's beauty. Enjoy a round of golf at Lake Henry Golf Club, embracing the outdoor spirit. For a unique twist, visit SkateWorld for a fun, relaxing skating experience, just 20.9km from Winter Haven's heart.

Adventure

Experience the thrill of freefall at Jump Florida Skydiving, located 14.5km from Winter Haven. For water enthusiasts, Chain Of Wakes offers exciting wakeboarding adventures in the heart of the city. Additionally, the Winter Haven City Tennis Center provides a fantastic venue for tennis enthusiasts seeking an active day out.

Nightlife

In Winter Haven, immerse yourself in the lively atmosphere at Indigo's Family Fun Center, a vibrant drinking pub offering romance and entertainment. Enjoy a delightful evening with friends, where laughter and good spirits create a memorable night out in this charming Florida town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Winter Haven

Winter Haven is an ideal destination for families and adventure seekers, offering a delightful mix of urban parks, lakes, and amusement parks. The area's attractions are perfect for those seeking outdoor activities, family fun, or a romantic getaway. With its charming surroundings, Winter Haven promises a memorable experience for every type of traveller.

  • LEGOLAND® Florida: Immerse yourself in a world of creativity and adventure at LEGOLAND® Florida. This family-friendly amusement park offers thrilling rides, interactive attractions, and captivating shows, all themed around the beloved LEGO® brand, making it a perfect destination for visitors of all ages.
  • The Circle B Bar Reserve: Experience the beauty of Florida's natural landscapes at The Circle B Bar Reserve, located 14.5km from Winter Haven. This nature preserve offers scenic trails for hiking and wildlife watching, providing a serene escape filled with opportunities for adventure and exploration.
  • Sanlan Bird and Wildlife Sanctuary: Just 16.1km from Winter Haven, Sanlan Bird and Wildlife Sanctuary is an eco-friendly haven where families can enjoy peaceful walks amidst diverse wildlife. This park promotes conservation and offers a unique chance to observe various bird species in their natural habitat.

Best time to go to Winter Haven

The best time to visit Winter Haven is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with moderate rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
February64.4°F (18.0°C)No RainMostly SunnyAverageAverage
March67.5°F (19.7°C)Light RainMostly SunnySlightly HighSlightly High
April72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June80.6°F (27.0°C)Moderate RainMostly SunnyAverageAverage
July81.7°F (27.6°C)Moderate RainMostly SunnyAverageAverage
August81.9°F (27.7°C)Moderate RainMostly SunnySlightly LowSlightly Low
September79.5°F (26.4°C)Moderate RainMostly SunnySlightly HighSlightly Low
October74.7°F (23.7°C)Light RainMostly SunnySlightly LowAverage
November68.0°F (20.0°C)No RainMostly SunnySlightly LowSlightly Low
December64.2°F (17.9°C)No RainMostly SunnyAverageSlightly High

Tips to save on your trip to Winter Haven

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Winter Haven during the low season (August to September and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Top hotels in Winter Haven

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
The price is €112 per night from 31 May to 1 Jun
€112
31 May - 1 Jun
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
Front staff was great

Reviewed on 9 May 2026

Holiday Inn Winter Haven by IHG
Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

3.5 out of 5
5801 Roosevelt Dr Winter Haven FL
Fully refundableReserve now, pay when you stay
The price is €122 per night from 17 May to 18 May
€122
17 May - 18 May
includes taxes & fees
9.4/10 Exceptional! (1,261 reviews)
Good for families

Reviewed on 12 May 2026

Best Western Plus Winter Haven Inn & Suites 
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
Fully refundableReserve now, pay when you stay
The price is €81 per night from 20 May to 21 May
€81
20 May - 21 May
includes taxes & fees
7.2/10 Good! (1,011 reviews)
Everything about this property was wonderful. We enjoyed our stay very much!

Reviewed on 11 May 2026

Howard Johnson by Wyndham Winter Haven FL
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.