Winter Haven Holidays from £758

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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.
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
per person
4 Oct - 11 Oct
found 16 hours ago
Return direct flight included
London (LHR) to Tampa (TPA)
9/10 Wonderful! (1,009 reviews)
Excellent property! It was clean, affordable, and very close to the beach.

Reviewed on 15 Jul 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
per person
4 Oct - 11 Oct
found 1 day ago
Return direct flight included
London (LHR) to Tampa (TPA)
9.4/10 Exceptional! (2,352 reviews)
The hotel is very nice.There are a lot of activities for the guests. We wished the pool was bigger. We were a party of three with two full-size beds in the room and we had to request for an additional robe an additional bottle of water. Everything is for two people. The hotel gives at the beach one umbrella and two chairs per room booked. It shouldn’t be this way. It should be by how many people are in the room. There could be four people in the room so we have to pay an additional amount for the umbrella and for additional chairs and that isn’t right. Also, the bathroom needs more hooks for towels and robes. I like that the shower had a bar in the bottom so I can shave my legs. It was a nice detail. We also thought that the staff at the front desk wasn’t very friendly. Also, the staff at the desk on the side where I think you can book things weren’t friendly either.

Reviewed on 15 Jul 2025

The Avalon Club

The Avalon Club

4 out of 5
per person
23 Aug - 28 Aug
found 8 hours ago
Return direct flight included
London (LON) to Tampa (TPA)
9.4/10 Exceptional! (430 reviews)
Beautiful property I would highly recommend this place to anyone looking for clean,friendly,convenience with a beautiful view.

Reviewed on 10 Jul 2025

The Hotel Zamora

The Hotel Zamora

4 out of 5
per person
23 Aug - 28 Aug
found 8 hours ago
Return direct flight included
London (LON) to Tampa (TPA)
8.2/10 Very Good! (109 reviews)
Great place for a weekend getaway. Will definitely be back!

Reviewed on 7 Jul 2025

Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
per person
4 Oct - 11 Oct
found 16 hours ago
Return direct flight included
London (LHR) to Tampa (TPA)
8.8/10 Excellent! (1,164 reviews)
The elevator didn’t work on my floor or section so you had to walk across the parking lot to get in the elevator. The ice machine didn’t work on our floor and the vending machine didn’t work on our floor. Everybody was nice and polite and professional in the room was beautiful just minor inconvenience

Reviewed on 11 Jul 2025

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

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 £105 per night from 3 Aug to 4 Aug
£105
3 Aug - 4 Aug
includes taxes & fees
9.4/10 Exceptional! (886 reviews)
"Good"

Reviewed on 14 Jul 2025

Best Western Plus Winter Haven Inn & Suites 
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 £106 per night from 20 Jul to 21 Jul
£106
20 Jul - 21 Jul
includes taxes & fees
9.6/10 Exceptional! (424 reviews)
"Amazing stay! Clean and amazing rooms. AC that will rock your socks off lol Will be coming back"

Reviewed on 13 Jul 2025

Staybridge Suites Winter Haven Auburndale by IHG
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way, Winter Haven, FL
The price is £265 per night from 10 Aug to 11 Aug
£265
10 Aug - 11 Aug
includes taxes & fees
10/10 Exceptional! (3 reviews)
"I had six grandkids and they all love playing with the Legos! Very convenient having the theme park next-door. We were disappointed some of the things were closed, but overall, it was a good experience."

Reviewed on 2 Jul 2025

Legoland Florida Hotel
See all 38,444 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

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

£62
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.