Winter Haven Holidays from £685

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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.
Clearwater Beach Hotel Suites

Clearwater Beach Hotel Suites

2.5 out of 5
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
London (LON) to Tampa (TPA)
No reviews
Great Hotel, comfortable bed, nice pool

Reviewed on 26 Jul 2025

The Avalon Club

The Avalon Club

4 out of 5
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
London (LON) to Tampa (TPA)
9.4/10 Exceptional! (430 reviews)
The property was really nice! I stood in a 2 bedroom and the ocean view was spectacular. There was always someone available if I needed anything and it was a jump, skip and hop away from the beach. Everything is within walking distance of the property. Gas station was right around the corner and a cute park across the street if you have little kiddies. I would stay in this property again and very soon :)

Reviewed on 31 Jul 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
London (LON) to Tampa (TPA)
9.2/10 Wonderful! (1,040 reviews)
Everything is great. Lacking food on the property and roof top bar doesn’t exist anymore

Reviewed on 1 Aug 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
London (LON) to Tampa (TPA)
9.4/10 Exceptional! (2,352 reviews)
Fun! And great if you are traveling with children!

Reviewed on 3 Aug 2025

Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

4 out of 5
Downtown St. Petersburg
per person
22 Oct - 29 Oct
found 24 hours ago
Return flight included
London (LGW) to Tampa (TPA)
7.6/10 Good! (1,001 reviews)
Great hotel , clean , staff is friendly

Reviewed on 31 Jul 2025

Things to do in and around Winter Haven

Winter Haven is an ideal destination for families seeking adventure and outdoor activities. Enjoy a range of attractions, including a resort, an amusement park, and shopping areas. Notable experiences include visiting local golf courses, exploring fascinating aircraft collections, and delving into the flight museum. Whether you're looking for relaxation or excitement, Winter Haven offers something for everyone.

Shopping

In Winter Haven, visit Northgate Shopping Center for a vibrant atmosphere and various shops. Havendale Plaza, only 11.3km away, offers similar vibes. If you're up for a drive, Eagle Ridge Mall, 14.5km from Winter Haven, features a vast selection of stores and entertainment options.

Recreation

Willowbrook Golf Course offers a tranquil golfing experience amidst lush greenery in Winter Haven. Alternatively, Southern Dunes Golf and Country Club, located 16.1km away, provides a stunning backdrop for a round of golf. For outdoor activities, Chain of Lakes Park features a vibrant atmosphere for sports enthusiasts.

Adventure

At Chain Of Wakes, experience exhilarating water sports that offer an adrenaline rush amidst the beautiful scenery of Winter Haven. For a fun-filled day, visit Indigo's Billiards, Bowling & Games, where family-friendly arcade adventures await. Don’t miss the Winter Haven City Tennis Center for thrilling tennis matches.

Nightlife

Winter Haven's nightlife offers a vibrant atmosphere at Indigo's Family Fun Center, a lively drinking pub where you can enjoy entertainment and a romantic vibe. It's the perfect spot to unwind with friends while sipping on delicious drinks and soaking in the lively surroundings.

*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, Florida, is an ideal destination for families seeking outdoor adventures. With a variety of attractions such as picturesque lakes, amusement parks, and urban parks, there’s something for everyone. Whether you're after a day of fun at an amusement park or a relaxing experience by the water, Winter Haven offers a delightful blend of outdoor activities and family-friendly experiences that make for a memorable holiday.

  • LEGOLAND® Florida: Experience a world of creativity and adventure at LEGOLAND® Florida, where families can explore interactive rides, shows, and attractions inspired by the beloved LEGO® brick. With themed areas like Miniland USA, featuring iconic landmarks built from millions of LEGO® bricks, and thrilling rides for all ages, it's a perfect destination for family fun in the sun.
  • Bok Tower Gardens: Just 17.7km from Winter Haven, Bok Tower Gardens offers a serene escape into beautifully landscaped gardens surrounding a stunning historic tower. The gardens are rich in cultural heritage and are home to diverse flora, making it a tranquil spot for leisurely strolls and enjoying nature's beauty.
  • Grand Hotel: Located 19.3km away, the Grand Hotel is a charming monument that showcases rich history and cultural significance. Visitors can admire its impressive architecture and learn about its role in the local heritage, providing a glimpse into the past while enjoying the picturesque surroundings.

Best time to go to Winter Haven

The best time to visit Winter Haven is dependant 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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Winter Haven.
  • 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

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 £78 per night from 10 Aug to 11 Aug
£78
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Only problem I had was with the curtains closing completely in the corner windows which left us slightly exposed. We worked around it so I still gave it 5 stars."

Reviewed on 22 Jul 2025

Holiday Inn Winter Haven by IHG
Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

3 out of 5
305 5th St NW and Avenue D NW, Winter Haven, FL
Fully refundable
The price is £107 per night from 4 Aug to 5 Aug
£107
4 Aug - 5 Aug
includes taxes & fees
9.6/10 Exceptional! (474 reviews)
"It is a very brand new hotel. Nothing to complain. The room is very clean. We really like it!"

Reviewed on 1 Aug 2025

Staybridge Suites Winter Haven Auburndale 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 £107 per night from 5 Aug to 6 Aug
£107
5 Aug - 6 Aug
includes taxes & fees
9.4/10 Exceptional! (929 reviews)
"Everything"

Reviewed on 31 Jul 2025

Best Western Plus Winter Haven Inn & Suites 
See all 38,430 properties in Winter Haven
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Legoland Florida which includes a river or creek, a garden and a pond

LEGOLAND® Florida

4.5/5(7 reviews)

Take the kids to this dynamic theme park for a day full of exciting rides, LEGO® brick creations and the chance to build your own LEGO®robots.

LEGOLAND® Florida

Indigo's Family Fun Center

Enjoy a stop at Indigo's Family Fun Center, an entertaining place to visit in Winter Haven. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Indigo's Family Fun Center

Cypresswood Golf and Country Club

Enjoy a round of golf in Winter Haven at Cypresswood Golf and Country Club. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Cypresswood Golf and Country Club

What to do in Winter Haven

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

£49
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Ladies Luncheon Pontoon Tour

Ladies Luncheon Pontoon Tour (Gentleman welcome)

£74
per adult
Ladies Luncheon Pontoon Tour (Gentleman welcome)
See all activities in Winter Haven

Frequently asked questions

Why should I book my Winter Haven holiday with Expedia?
Choose Expedia to arrange your next big escape simply and all in one convenient place. Our insider tip for scoring a great deal on a Winter Haven retreat? Bundle your accommodation, flights and/or hire car into a package holiday. Then throw in a few fun tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to stress if you have to change your travel plans. Round-the-clock help with changing and cancelling your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Winter Haven?
Peak season falls in February, March and July and is an exciting time to visit — if you don't mind rubbing elbows with the crowds. January, September and October are generally quieter times of the year. Arrange your getaway to Winter Haven according to what type of holiday you're looking for. January is the coolest time of year, when daytime temperatures average 15ºC. In June, the warmest month, you will experience temperatures of around 27ºC during the day.
What are the top hotels for my holiday in Winter Haven?
Econo Lodge Winter Haven Chain Of Lakes and Courtyard by Marriott Winter Haven are some favourite getaways in the Cypress Gardens neighbourhood. If you prefer to spend time in the Inwood area, lock in a room at Holiday Inn Winter Haven, an IHG Hotel or Rodeway Inn & Suites Winter Haven Chain Of Lakes.
How do I get a cheap holiday to Winter Haven?
Booking a hotel and flight together with Expedia won't just save you time — it'll save you a tidy sum too. A Winter Haven holiday makes it simple to put together the ideal trip. With more than 400 airlines around the world to choose from, finding convenient flights that fit your schedule won't be a challenge. On top of that, we have over 321,000 properties globally to select from. Now that's what we call choice. Whatever your budget, Expedia puts the world within your reach. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Winter Haven holiday?
With major attractions like LEGOLAND® Florida and Chain of Lakes Park, a holiday in Winter Haven is packed with fun things to do and see. Winter Haven Hospital and The Circle B Bar Reserve are two other sights worth exploring.
What is the best neighbourhood to stay in when on holiday in Winter Haven?
There are loads of appealing neighbourhoods to stay in Winter Haven, but Cypress Gardens is hard to look past. LEGOLAND® Florida is just one of the reasons it's such a hit.
Do I need a visa for my Winter Haven holiday?
Visa requirements for Winter Haven vary depending on your nationality and purpose of your visit. Check official government websites to determine if you need a visa for your holiday. They'll give you the most up-to-date information, including details about application procedures or any supporting documentation you might need. Enquire about your visa requirements in advance to ensure a travel experience that's hassle free. Also make sure your passport is valid for a further six months from the date of your return.
What should I wear on my Winter Haven holiday?
Though everyone's style varies, it can be helpful to have some guidelines for what to bring during your holiday in Winter Haven. Think about browsing social media before you go for inspiration on local dress codes or fashion trends. Be sure to check the local weather forecast so you can pack appropriately. The warmest month in Winter Haven is June, with average daily temperatures of 27ºC. If you're on holiday during the coolest month of January, the mercury averages 15ºC during the day.
What does an Expedia Winter Haven holiday include?
It's up to you! Simply choose from a range of Winter Haven bundles, such as a flight, hire car and hotel. You can also book a flight with a hotel, or a flight and a car hire. Once you've made your booking, add on the fun stuff like activities and tours. Whatever your Winter Haven getaway looks like, get ready to save! Discover a wide range of property types and choose one that suits your travel needs. The most popular holiday rentals here are private holiday homes and hotel resorts. With Expedia, it's a breeze to tailor your Winter Haven escape however you want.
Does Expedia offer Book Now, Pay Later Winter Haven holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has come up with a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a fantastic getaway without exhausting your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that suit all types of budgets, so you can have that well-deserved holiday now.
  • No-deposit holidays: When you want to grab an incredible deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock it in.

Can I choose my airline with a Winter Haven Expedia holiday?
With a holiday package, you're the one in charge. Whether you're hoping to fly to Winter Haven in coach or first class, simply choose from the available airline options. Expedia has access to more than 400 partner airlines worldwide.

* 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.