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.

Winter Haven Holidays 2026 from £897

Top Winter Haven Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.

Saddlebrook Resort

Wesley Chapel South

£897

per person

30 Sept - 7 Oct

found 1 day ago

Return flight included

London (LHR) to Tampa (TPA)

8/10 Very good! (142 reviews)

SkyBeach Resort

Greater Pinellas Point

£1,058

per person

3 Oct - 10 Oct

found 1 day ago

Return flight included

London (LHR) to Tampa (TPA)

8.6/10 Excellent! (842 reviews)

The Barrymore Hotel Tampa Riverwalk

Downtown Tampa

£1,086

per person

30 Sept - 7 Oct

found 1 day ago

Return flight included

London (LHR) to Tampa (TPA)

8.6/10 Excellent! (2,722 reviews)

Very friendly staff, good restaurant in the lobby

Reviewed on 30 Jul 2026

Hilton St. Petersburg Bayfront

Downtown St. Petersburg

£978

per person

3 Oct - 10 Oct

found 1 day ago

Return flight included

London (LHR) to Tampa (TPA)

7.8/10 Good! (1,115 reviews)

Landing Apartments near Sun City Center and Riverview

£1,119

per person

30 Aug - 6 Sept

found 1 day ago

Return flight included

London (LHR) to Tampa (TPA)

8.6/10 Excellent! (31 reviews)

The apartment wasn’t completely ready. There was no ice, not enough towels, paper towels or toilet paper. I had to go buy our own supplies.

Reviewed on 15 Jul 2026

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	60.4°F (15.8°C)	Light Rain	Mostly Sunny	Average	Average
February	64.4°F (18.0°C)	No Rain	Mostly Sunny	Average	Average
March	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
April	72.9°F (22.7°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
May	77.2°F (25.1°C)	Light Rain	Mostly Sunny	Average	Average
June	80.6°F (27.0°C)	Moderate Rain	Mostly Sunny	Average	Average
July	81.7°F (27.6°C)	Moderate Rain	Mostly Sunny	Average	Average
August	81.9°F (27.7°C)	Moderate Rain	Mostly Sunny	Slightly Low	Slightly Low
September	79.5°F (26.4°C)	Moderate Rain	Mostly Sunny	Slightly High	Slightly Low
October	74.7°F (23.7°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	68.0°F (20.0°C)	No Rain	Mostly Sunny	Slightly Low	Slightly Low
December	64.2°F (17.9°C)	No Rain	Mostly Sunny	Average	Slightly 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.

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

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

200 Cypress Gardens Boulevard Winter Haven FL

Fully refundable

£82

30 Aug - 31 Aug

includes taxes & fees

LEGOLAND Beach Retreat

100 Legoland Way SE Winter Haven FL

£170

11 Aug - 12 Aug

includes taxes & fees

Legoland Florida Hotel

1 Legoland Way Winter Haven FL

£269

26 Aug - 27 Aug

includes taxes & fees

8.6/10 Excellent! (172 reviews)

"Nada que hacer"

Reviewed on 30 Jul 2026

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.

Stay near popular Winter Haven attractions