Question 1

What types of vacation packages are available in Winter Haven?

Accepted Answer

Winter Haven, known for its family-friendly attractions and outdoor activities, offers several vacation package styles:

Family-friendly package: A package built around a stay at Legoland Florida Hotel, rated 8 out of 10 by travelers, is ideal for families thanks to its family rooms and on-site waterpark.
Budget-friendly package: For value, consider a package with a stay at Howard Johnson by Wyndham Winter Haven FL, where travelers often note the cozy rooms. This hotel offers free breakfast and an outdoor pool.
Breakfast-included package: Staybridge Suites Winter Haven Auburndale by IHG, rated 9.5 out of 10 by travelers, is a great choice for packages that include breakfast, with guests frequently praising the excellent staff and great overall experience.
Pet-friendly package: Home2 Suites By Hilton Winter Haven, rated 9.2 out of 10 by travelers, welcomes pets and features kitchens in its rooms, with guests highlighting the awesome staff and clean facilities.

Question 2

How can I save money on a Winter Haven vacation package?

Accepted Answer

When you bundle, you can save up to 30%*. To save money on a Winter Haven package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

Question 3

How much does a Winter Haven vacation package cost?

Accepted Answer

A Winter Haven vacation package typically costs around $950 per adult for a weekend trip. Lower-priced options start around $550 per adult, while premium packages can reach up to $1,800.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

Question 4

How do I find cheap Winter Haven vacation package deals?

Accepted Answer

The cheapest Winter Haven vacation package deals can be as low as around $520 per adult for weekend trips. Separately, January typically has the lowest average monthly prices, around $720 per adult, for a 3-day trip, and October follows at around $900 per adult, also for a 3-day trip. Bundling flights and hotel together also typically saves money — nearly all Winter Haven packages include some savings versus booking separately, typically around $30 per adult for weekend trips. Week-long trips can save even more, often around $90 per adult. Browse cheap vacation packages in Winter Haven on Expedia for current deals.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

Question 5

What is the best time to go to Winter Haven?

Accepted Answer

The best time to go to Winter Haven for a pleasant climate is during the cooler months, particularly from December through February. Winters are mild, with daytime highs typically in the 70s°F and lows in the 50s°F, offering comfortable conditions for exploring the area's outdoor attractions.

While March, June, and July are peak booking months, the summer months are hot and humid, with highs around 95°F and a higher chance of thunderstorms. For those seeking a more budget-friendly Winter Haven vacation package, January, October, and February tend to offer lower prices, though January and February still benefit from the mild winter weather.

Question 6

What's included in a Winter Haven vacation package?

Accepted Answer

A Winter Haven vacation package lets you combine round-trip flights, a hotel stay, and a rental car. Many hotels here offer free breakfast, providing a convenient start to your day, and some also offer airport shuttle service to and from Orlando International Airport (MCO). These packages are ideal for exploring Winter Haven's family-friendly attractions.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

Question 7

What's the best vacation package for Winter Haven?

Accepted Answer

Families looking for the best Winter Haven vacation package can consider a stay at Legoland Florida Hotel, rated 8 out of 10 by travelers. This hotel is about a 5-minute walk from LEGOLAND® Florida and features family rooms and an on-site waterpark, making it a convenient base for theme park adventures.

For couples, a package with a stay at Courtyard by Marriott Winter Haven offers a comfortable experience. Rated 8.5 out of 10, this hotel includes a bar/lounge and an outdoor pool, and travelers often highlight the spacious rooms and friendly staff. Nightly rates here are around $200.

Travelers seeking a budget-friendly Winter Haven vacation package might choose Howard Johnson by Wyndham Winter Haven FL. With nightly rates around $100, this hotel provides free breakfast and an outdoor pool, and travelers often note the cozy rooms.

*Package availability and prices may change depending on dates and demand.

Question 8

Is Winter Haven a good choice for a family vacation package?

Accepted Answer

Winter Haven is a strong choice for family vacation packages, with most bookings being family trips. The destination is primarily known for its family-friendly attractions and outdoor activities, making it well-suited for travelers with children.

Many hotels cater to families, offering amenities like family rooms, outdoor pools, and even waterparks. For instance, Legoland Florida Hotel, rated 8 out of 10 by travelers, is designed with families in mind, featuring family rooms, an outdoor pool, and a waterpark, and is conveniently located about a 5-minute walk from LEGOLAND® Florida.

Beyond the hotels, families can enjoy attractions such as LEGOLAND® Florida and Peppa Pig Theme Park Florida, both about 5 miles from central Winter Haven, providing ample entertainment for all ages.

Question 9

What is the best time to book a Winter Haven vacation package?

Accepted Answer

Book your Winter Haven vacation package around 4 weeks in advance. This gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 2 and 9 weeks out.

March, from June to July are the most popular months for Winter Haven packages, so booking earlier is advisable if you're traveling during those times.

Question 10

What are the top things to do in Winter Haven?

Accepted Answer

A Winter Haven vacation offers plenty of family-friendly attractions and outdoor activities, making it a great spot for adventure and entertainment. You can easily fill your days with these popular sights:

Browse and book things to do in Winter Haven on Expedia.

Question 11

How many days do you need for a Winter Haven vacation?

Accepted Answer

Most Winter Haven vacation packages last around 3 days, which is ideal for a focused trip. This allows enough time to visit key attractions like LEGOLAND® Florida and Peppa Pig Theme Park Florida, or to enjoy the natural beauty of Chain of Lakes Park.

Most travelers opt for weekend trips, while nearly a third choose week-long trips to explore more of the area's outdoor activities and family-friendly attractions. A longer stay could allow for day trips to nearby Orlando theme parks or more time enjoying Winter Haven's lakes.

Question 12

Is Winter Haven a good destination for a weekend vacation?

Accepted Answer

Winter Haven is an excellent choice for a weekend vacation package, with most travelers opting for 1 to 3-day trips. A typical Winter Haven vacation package lasts around 3 days, which is perfect for experiencing the main attractions.

During a weekend, you can easily visit family-friendly spots like LEGOLAND® Florida or Peppa Pig Theme Park Florida. You could also spend time enjoying the outdoors at Chain of Lakes Park, making it a fulfilling short getaway.

Question 13

Do you need to rent a car in Winter Haven, or is public transport enough?

Accepted Answer

For a Winter Haven vacation package, a rental car is generally the easiest way to get around and explore the area. While local commuter bus services like Winter Haven Area Transit and the Citrus Connection operate within the city, attractions and points of interest can be spread out, making a car more flexible for sightseeing.

If you're flying into the region, you'll likely arrive at Orlando International Airport (MCO) or Tampa International Airport (TPA), both of which are a drive away. Rental cars are readily available from major providers like Avis, Budget Car & Truck Rental, Enterprise Rent A Car, and Hertz Rent A Car, allowing you to easily reach your hotel and venture out to nearby family-friendly attractions.

Question 14

Are Winter Haven vacation package hotels conveniently located?

Accepted Answer

Winter Haven vacation package hotels offer a range of convenient locations, from central areas to those closer to major attractions. Many properties are situated to provide easy access to both the town's amenities and its popular theme parks.

For example, Staybridge Suites Winter Haven Auburndale by IHG is about a 5-minute walk from central Winter Haven, placing you close to downtown, while still being about 3 miles from LEGOLAND® Florida. The Holiday Inn Winter Haven by IHG is also well-located, about 1 mile from central Winter Haven and about 2 miles from LEGOLAND® Florida. If you prefer to be closer to the theme park, Home2 Suites By Hilton Winter Haven is about a 10-minute walk from LEGOLAND® Florida, though it's about 4 miles from central Winter Haven. This variety allows you to choose a hotel that best suits your itinerary, whether you prioritize downtown access or proximity to the parks.

Question 15

Can I change or cancel my Winter Haven vacation package if my plans change?

Accepted Answer

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Question 16

Do One Key members get extra savings when booking Winter Haven vacation packages?

Accepted Answer

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Question 17

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

Accepted Answer

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Winter Haven vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

Question 18

How do I find last-minute vacation packages to Winter Haven?

Accepted Answer

To find last-minute vacation packages to Winter Haven, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

Question 19

How does free cancellation work on Winter Haven vacation packages?

Accepted Answer

Free cancellation on a Winter Haven vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Question 20

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

Accepted Answer

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Winter Haven getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Question 21

Why should I book my Winter Haven vacation package with Expedia?

Accepted Answer

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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

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

Winter Haven Vacations from $368

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Winter Haven Vacation

The Latest Winter Haven vacation packages

Blue Wave Suites

Ocean Club Treasure Island Hotel

Hibiscus Suites - Gateway to Siesta Key

Cedar Cove Resort and Cottages

ChartHouse Clearwater Beach Marina Hotel

Stay near popular Winter Haven attractions

LEGOLAND® Florida

What to do in Winter Haven

LEGOLAND® Florida Tickets

LEGOLAND Florida FasTrack Pass

Ladies Luncheon Pontoon Tour (Gentleman welcome)

Winter Haven Hotel Deals

Holiday Inn Winter Haven by IHG

Best Western Plus Winter Haven Inn & Suites

Staybridge Suites Winter Haven Auburndale by IHG

Find the Best Winter Haven Vacation Packages

Things to do in and around Winter Haven

Find the best attractions in and around Winter Haven

Best time to go to Winter Haven

Tips to save on your trip to Winter Haven

Winter Haven Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app