Winter Haven Holidays from £963

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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.
Captiva Beach Resort

Captiva Beach Resort

South Village
£963
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
London (LHR) to Tampa (TPA)
9/10 Wonderful! (1,303 reviews)
Stayed 09/18/2026 and as usual... it was perfect! Always clean, comfortable and affordable. Thank you for a wonderful stay.

Reviewed on 20 Sept 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
Save 100% on your flight
£1,153
per person
21 Nov - 28 Nov
found 15 hours ago
Return direct flight included
Manchester (MAN) to Tampa (TPA)
9.6/10 Exceptional! (1,190 reviews)
Won’t Be Staying Here Again! Very disappointing experience. We were told over the phone around 1 PM that our room was available for early check-in and that we could go to the hotel. The man I spoke with was not particularly helpful and initially told me that the only way to find out was to come to the hotel. I specifically explained that I didn’t want to drive there just to find out that we had to wait and asked if he could simply check whether a room was available. He then told me that our room was available and that we could come. We left the beach specifically to go to the hotel (4 adults, a kid, and a dog), only to arrive around 2:15 PM and be told the room wasn’t ready yet but would be soon. No one followed up with us, and we ended up waiting for almost **2 hours** until I had to go back to the front desk at 4 PM (our official check-in time) to ask about the room. Also, we had an extra car and were told parking was completely full, forcing us to park elsewhere and pay a significant amount. However, we noticed many empty spaces throughout the night (up to 1 am), which made it feel like the front desk simply didn’t want to help. On top of that, the $80/day pet fee seemed very unreasonable. The property itself was nice, but the poor communication, parking situation, and extra fees made the stay frustrating. **We would not stay here again.**

Reviewed on 20 Sept 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

Save 100% on your flight
£1,364
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
London (LHR) to Tampa (TPA)
9.2/10 Wonderful! (591 reviews)
A place to relax and enjoy the beach.

Reviewed on 20 Sept 2026

Landing Tampa Westshore

Landing Tampa Westshore

Port Tampa City
Save 100% on your flight
£1,351
per person
23 Nov - 30 Nov
found 1 day ago
Return flight included
London (LHR) to Tampa (TPA)
9/10 Wonderful! (197 reviews)
All was wonderful. We had a problem with the concrete curbs. The curb grabbed our bumper and pulled the front end of our bumper off when we had to back out. It has cost us several thousand dollars for the repairs. Otherwise it was a beautiful facility.

Reviewed on 21 Sept 2026

Inn on the Beach - 18+ only

Inn on the Beach - 18+ only

Pass-a-Grille
£1,284
per person
21 Nov - 28 Nov
found 15 hours ago
Return direct flight included
Manchester (MAN) to Tampa (TPA)
9.8/10 Exceptional! (444 reviews)
Fantastic property! The Inn on the Beach is right on the beach. Staff is amazing. Loved the access to beach chairs and towels. Highly recommend!

Reviewed on 16 Sept 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.

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

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
£92
27 Sept - 28 Sept
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Room with king size bed. Comfortable and clean. Nice desk but I didn’t really have a chance to use it since I was only there overnight. Breakfast was included. It was ok. Nothing special,"

Reviewed on 20 Sept 2026

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

Best Western Plus Winter Haven Inn & Suites 

5801 Roosevelt Dr Winter Haven FL
Fully refundableReserve now, pay when you stay
£102
23 Sept - 24 Sept
includes taxes & fees
Best Western Plus Winter Haven Inn & Suites 
Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

305 5th St NW and Avenue D NW Winter Haven FL
Fully refundable
£105
23 Sept - 24 Sept
includes taxes & fees
Staybridge Suites Winter Haven Auburndale by IHG
See all 38,501 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
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Holiday in Month
Where to go when
Where to go when

Stay near popular Winter Haven attractions

The entrance to LEGO Florida with colorful LEGO structures and a large LEGO sign.

LEGOLAND® Florida

9.0/10 (2,150 reviews)
LEGOLAND Florida Resort captivates families with 50+ rides and attractions for children aged 2-12. Explore themed worlds with interactive adventures, family-friendly coasters, and impressive LEGO replicas.
See properties
A narrow water channel surrounded by lush greenery and tall trees.

Chain of Lakes Park

8.2/10 (185 reviews)
Navigate through 22 interconnected lakes in this serene Florida park, a haven for water enthusiasts. Rent a boat to explore the unique canal system connecting these diverse aquatic environments.
See properties

Peppa Pig Theme Park Florida

The world's first Peppa Pig theme park offers rides and play areas designed for preschoolers. Families can enjoy Daddy Pig's Roller Coaster and meet beloved characters in this colourful, interactive environment.
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Theatre Winter Haven

7.4/10 (56 reviews)
Theatre Winter Haven delivers captivating community productions in an intimate setting with excellent acoustics. Secure tickets in advance to experience classic plays and musicals in this cultural cornerstone.
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Indigo's Family Fun Center

6.6/10 (19 reviews)
This laid-back entertainment venue combines bowling, billiards, and arcade games under one roof. Spend an evening challenging friends to friendly competition while enjoying drinks from the bar area.
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Inman Park

7.4/10 (14 reviews)
Inman Park is just one of the places to see in Winter Haven, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
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Cypresswood Golf and Country Club

6.4/10 (25 reviews)
Designed by Ron Garl, this championship golf course challenges players amid Florida's natural landscape. Enjoy a round followed by live music and dining at the clubhouse on Thursday through Saturday evenings.
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Willowbrook Golf Course

6.8/10 (15 reviews)
Enjoy a round of golf in Winter Haven at Willowbrook Golf Course. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
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What to do in Winter Haven

LEGOLAND Florida FasTrack Pass

LEGOLAND Florida FasTrack Pass

£64
per traveller
LEGOLAND Florida FasTrack Pass
Ladies Luncheon Pontoon Tour

Ladies Luncheon Pontoon Tour (Gentleman welcome)

£73
per adult
Ladies Luncheon Pontoon Tour (Gentleman welcome)
Winter Haven: Coffee, Tea & Dessert Food Tour

Winter Haven: Coffee, Tea & Dessert Food Tour

£98
per adult
Winter Haven: Coffee, Tea & Dessert Food Tour
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.

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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.