How much does a Winter Haven vacation package cost?

You'll find cheap prices from $451 on Expedia for your Winter Haven getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Winter Haven costs.

What are the cheapest months to go to Winter Haven?

January, September and October are the best times to search for cheap Winter Haven vacation packages. Opting to travel in quieter months means you can usually find reduced prices on hotels and flights.

How many days is enough for Winter Haven?

Winter Haven vacations come in various shapes and sizes, but to get a true feel for this place, we reckon 2 days is about right. This will mean you can fit in headline attractions like Indigo's Billiards, Bowling & Games and Chain of Lakes Park and seek out some hidden gems. Don't skip cool neighborhoods such as Cypress Gardens and Inwood either. If you're clever with your time, you can even allow for a day trip from Winter Haven too.

Is it worth booking a vacation package to Winter Haven?

Popular for its golfing, hiking and views, a Winter Haven vacation is a hit with all types of travelers. Be sure to visit key sights like Chain of Lakes Park and Theatre Winter Haven , and consider renting a set of wheels for day trips to experience even more.

How to find the best Winter Haven package deals?

Use Expedia's filters to find some of the best Winter Haven package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Winter Haven package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.

Is it cheaper to book a Winter Haven vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can tailor your Winter Haven trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.

When to book a vacation package to Winter Haven?

Score incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Winter Haven getaway.

How to plan a trip to Winter Haven?

Choose when to go: Check your diary and get your bags packed. Your preferred season and the type of activities available will also help you decide when to escape to Winter Haven. Figure out your budget: Make sure you have enough money to pay for everything from food and transportation to activities and airfares. Your accommodations will likely be the largest expense during your trip to Winter Haven. Use Expedia's trip planning tool to discover Winter Haven: Research every aspect of your trip to Winter Haven with this handy planner. Invite family or friends to collaborate on a group getaway, search for stays or things to do and make bookings. Decide how many days away: Start by listing all the sights and activities you want to get to in Winter Haven. Then, estimate how long you'll need at each, including any travel time. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick a Winter Haven vacation package that brings all your bookings together. Book activities and experiences in advance: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Winter Haven. Find all the exciting things to do in Winter Haven with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Winter Haven vacation packages?

If you're anything like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Winter Haven vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

Winter Haven Vacation Packages 2026 from $451

Name: Legoland Florida Hotel
Price range: $340 total
Rating: 8.8

Your Winter Haven Vacation

When a city getaway is calling, answer it with a Winter Haven vacation package. The neighborhood 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 vacation is just a few clicks away with Expedia.

The Latest Winter Haven vacation packages

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

Mar Bay Motel &Suites

Save 100% on your flight

$451

per person

Mar 14 - Mar 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (60 reviews)

Excellent customer service

Reviewed on Dec 14, 2025

Saddlebrook Resort

Wesley Chapel South

Save 100% on your flight

$519

per person

Mar 17 - Mar 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

No reviews

The resort is absolutely beautiful.We will definitely be staying here again.We actually decided to stay another night. What definitely recommended

Reviewed on Jan 1, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

$1,629

per person

Apr 2 - Apr 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (712 reviews)

Staff was very accommodating and the Jr. Suite pleasant to come back to after my little adventures.

Reviewed on Jan 10, 2026

Plaza Beach Hotel Beachfront Resort

$1,693

per person

Apr 2 - Apr 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,000 reviews)

We were pleasantly surprised with how clean the room was when we arrived and had everything we needed. The walk from our room to the beach was about 4 seconds... perfect.

Reviewed on Jan 10, 2026

The Barrymore Hotel Tampa Riverwalk

Downtown Tampa

Save 100% on your flight

$769

per person

Mar 28 - Apr 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.4/10 Very Good! (2,509 reviews)

I was not able to get breakfast, or even get a coffee. Many patrons walked out after waiting a long time, including myself. The restaurant was only about 75% full, and the wait staff was working exceptionally hard and moving fast but we’re unable to bring out any food and had exceptionally long walks to the back of the building or something. Even for people to get their check to cash out took a long time. I do not know if they’re just understaffed or the cooks were taking forever to get the food out or they had a long walk to even get the food. But I definitely do not recommend going to breakfast there. The rest of the place was OK.

Reviewed on Jan 9, 2026

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Winter Haven Hotel Deals

Best Western Plus Winter Haven Inn & Suites

5801 Roosevelt Dr Winter Haven FL

Fully refundableReserve now, pay when you stay

$145 nightly

$163 total

Jan 12 - Jan 13

Total with taxes and fees

9.4/10 Exceptional! (1,106 reviews)

Clean

Reviewed on Jan 5, 2026

Legoland Florida Hotel

1 Legoland Way Winter Haven FL

$303 nightly

$340 total

Jan 12 - Jan 13

Total with taxes and fees

8.8/10 Excellent! (58 reviews)

Location, theming, activities were amazing

Reviewed on Jan 3, 2026

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

Fully refundableReserve now, pay when you stay

$218 nightly

$245 total

Jan 12 - Jan 13

Total with taxes and fees

8/10 Very Good! (8,934 reviews)

Great property.

Reviewed on Jan 10, 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.

Things to do in and around Winter Haven

Winter Haven is perfect for family-friendly adventures, offering a variety of activities such as exciting amusement parks, a thrilling water park, and beautiful resort accommodations. Visitors can enjoy beach vacations, themed attractions, and festive holiday events, making it an ideal destination for fun and relaxation. Don't miss the chance to experience the vibrant shopping areas and exhilarating rides that Winter Haven has to offer.

Shopping

The nearest shopping spot is Northgate Shopping Center, offering a lively mix of entertainment and family-friendly options. Havendale Plaza Shopping Center, located 7 miles away, features similar vibes. If you're up for a drive, check out Eagle Ridge Mall, 9 miles from Winter Haven, for a broader selection.

Recreation

Chain of Lakes Park offers a vibrant atmosphere for sports enthusiasts, perfect for jogging or a leisurely walk. Theatre Winter Haven immerses visitors in culture with its engaging performances, ideal for family outings. For golf lovers, Lake Henry Golf Club provides a scenic outdoor experience on its well-maintained greens.

Adventure

Experience the thrill of gaming at Indigo's Billiards, Bowling & Games, perfect for family fun. Hike the scenic Fort Fraser Trail, surrounded by nature's beauty, or take to the skies with Jump Florida Skydiving for an exhilarating aerial adventure, both located a short drive from Winter Haven.

Nightlife

Winter Haven's nightlife offers a unique blend of fun and romance at Indigo's Family Fun Center. Enjoy a vibrant atmosphere with drinks and entertainment, making it the perfect spot to unwind and socialize after a long day of exploring. Experience the local charm and vibrant energy of this lively pub.

*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 family-friendly outdoor adventures. With its stunning lakes, exciting amusement parks, and beautiful urban parks, visitors can enjoy a variety of activities that cater to both adventure seekers and those looking for a relaxing beach experience. Whether you're exploring nature or having fun at local attractions, Winter Haven promises memorable experiences for travelers of all ages.

LEGOLAND® Florida: Dive into a world of creativity and imagination at LEGOLAND® Florida, where families can enjoy thrilling rides, interactive attractions, and stunning LEGO-themed displays. Perfect for kids and the young at heart, this amusement park promises a day full of adventure and fun.
Auburndale City Park: Just 5 miles from Winter Haven, Auburndale City Park offers a serene escape with lush green spaces, playgrounds, and picnic areas. It's an ideal spot for families seeking outdoor activities, walking trails, and a taste of city life in a relaxing environment.
The Circle B Bar Reserve: Located 9 miles from Winter Haven, this nature preserve invites you to explore its scenic trails and diverse wildlife. Ideal for adventure enthusiasts, it offers opportunities for hiking, birdwatching, and connecting with Florida's natural beauty.

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 to Winter Haven during the low season (August to September and November) for more affordable options.
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	70ºF
Max Temp Summer	90ºF
Top Sights	LEGOLAND® Florida, Theatre Winter Haven and True Blue Winery

Language

English

Currency

U.S dollars

Population

33,900

Max Temp Winter

70ºF

Max Temp Summer

90ºF

Top Sights

LEGOLAND® Florida, Theatre Winter Haven and True Blue Winery