Winter Haven Holidays from £905

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Your Winter Haven Holiday

When a city getaway is calling, answer it with a Winter Haven holiday package. The neighbourhood of Fussels Corner, which is great for golfing, nature and walking, makes a fantastic base for your adventures. You'll want to take in some sights during your trip to Winter Haven. Carve out some time for popular attractions like LEGOLAND® Florida, Chain of Lakes Park and Auburndale City Park. Don't put off visiting this destination any longer. The perfect Winter Haven holiday is just a few clicks away with Expedia.

Top Winter Haven Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Family Home Tampa
Hotel Tampa Riverwalk
Saddlebrook Resort
The Barrymore Hotel Tampa Riverwalk
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

Things to do in and around Winter Haven

Winter Haven is perfect for families seeking outdoor adventures and leisure activities. Visitors can enjoy a variety of attractions, including a resort, an amusement park, and vibrant shopping areas. Key highlights include a renowned golf course and a fascinating flight museum showcasing impressive aircraft collections, ensuring a memorable experience for all. Whether you're seeking relaxation or excitement, Winter Haven has something to offer for everyone.

Shopping

In Winter Haven, you can enjoy shopping at Northgate Shopping Center, which offers a vibrant mix of entertainment and family-friendly options. Havendale Plaza, located 11.3km away, is another great spot. If you're up for a drive, Southgate Shopping Center, 14.5km away, also features a variety of shops and activities.

Recreation

At Lake Henry Golf Club, enjoy a round of golf amidst serene surroundings, perfect for relaxation and outdoor activity. Baytree Golf Club offers a similarly invigorating experience with its lush greens. Southern Dunes Golf and Country Club, located 16.1km away, boasts remarkable views and a challenging course for golf enthusiasts.

Adventure

Experience the thrill of freefall with Jump Florida Skydiving, located 14.5km from Winter Haven. For water enthusiasts, Chain Of Wakes offers exhilarating water sports right in the heart of Winter Haven. Enjoy family fun at Indigo's Billiards, Bowling & Games, where adventure meets entertainment in a vibrant atmosphere.

Nightlife

Winter Haven boasts a lively nightlife scene, perfect for unwinding after a day of exploration. Visit Indigo's Family Fun Center, a delightful drinking pub offering entertainment and a romantic atmosphere, ideal for couples or friends looking to enjoy a fun evening together.

*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 excellent destination for families seeking outdoor adventures. With its stunning lakes, exciting amusement parks, and inviting urban parks, there's plenty to explore. Whether you're after a fun day out with the family or a relaxing beach experience, the local attractions cater to all types of travellers looking to enjoy the great outdoors in this charming Floridian city.

  • LEGOLAND® Florida: Immerse yourself in a world of creativity and adventure at LEGOLAND® Florida, where interactive rides, attractions, and shows cater to families. Explore intricately crafted LEGO landscapes and engage in hands-on experiences that spark imagination in visitors of all ages.
  • Bok Tower Gardens: Discover the tranquil beauty of Bok Tower Gardens, a historic site featuring stunning landscapes and a magnificent carillon tower. Wander through lush gardens, enjoy the melodious sounds of the bells, and appreciate the rich cultural heritage that this serene oasis offers.
  • Cypresswood Golf and Country Club: Experience family-friendly golfing at Cypresswood Golf and Country Club, where well-maintained courses and picturesque surroundings provide an enjoyable day out. Perfect for both beginners and seasoned players, it offers a welcoming atmosphere for all.

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 during the off-peak season (typically August to September and November) for more affordable package holidays to Winter Haven.
  • 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.

Winter Haven Essential Information

Language
English
Currency
U.S dollars
Population
33,900
Max Temp Winter
21ºC
Max Temp Summer
32ºC
Top Sights
LEGOLAND® Florida, Theatre Winter Haven and True Blue Winery

Top hotels in Winter Haven

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
The price is £83 per night from 15 Feb to 16 Feb
£83
15 Feb - 16 Feb
includes taxes & fees
7/10 Good! (1,016 reviews)
Decent price for pet friendly room.

Reviewed on 9 Feb 2026

Howard Johnson by Wyndham Winter Haven FL
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
The price is £174 per night from 10 Mar to 11 Mar
£174
10 Mar - 11 Mar
includes taxes & fees
9/10 Wonderful! (159 reviews)
Good

Reviewed on 2 Feb 2026

LEGOLAND Beach Retreat
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
The price is £244 per night from 2 Mar to 3 Mar
£244
2 Mar - 3 Mar
includes taxes & fees
8.8/10 Excellent! (72 reviews)
We had the absolute best time at the Legoland Pirate Island Hotel with my two little boys (5 and 7). The lobby is so much fun (they loved playing in the castle with other kids and building lego), we enjoyed the PJ Dance Party at night and a little show before that. The decor is perfect for any kid ...

Reviewed on 7 Feb 2026

Legoland Florida Hotel
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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What to do in Winter Haven

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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. Flight-inclusive packages are ATOL protected.