Winter Haven Vacations

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Find the Best Winter Haven Vacation Packages

Winter Haven Hotel Deals

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven

3 out of 5
6015 Cypress Gardens Blvd Winter Haven FL
Fully refundableReserve now, pay when you stay
The price is SAR 537 per night from Dec 7 to Dec 8
SAR 537
SAR 602 total
7 Dec - 8 Dec
includes taxes & fees
9.4/10 Exceptional! (241 reviews)
Very spacious room and clean hotel. Only issue was the water temp in shower/tub didn’t stay constant and got so hot I had to get out.

Reviewed on 23 November 2025

Home2 Suites By Hilton Winter Haven
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 SAR 521 per night from Dec 21 to Dec 22
SAR 521
SAR 584 total
21 Dec - 22 Dec
includes taxes & fees
9.6/10 Exceptional! (655 reviews)
Room was clean and very roomy. Quiet and very friendly staff.

Reviewed on 26 November 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 SAR 916 per night from Dec 7 to Dec 8
SAR 916
SAR 1,173 total
7 Dec - 8 Dec
includes taxes & fees
9/10 Wonderful! (47 reviews)
Staff was great. Very accommodating.

Reviewed on 24 November 2025

Legoland Florida Hotel
See all 39,528 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.

Discover the most popular places to visit in Winter Haven

Legoland Florida which includes a pond, a river or creek and rides

LEGOLAND® Florida

Have a fun-filled day at LEGOLAND® Florida and find out why this is a popular theme park in Winter Haven. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

LEGOLAND® Florida

Chain of Lakes Park

Catch an event at Chain of Lakes Park during your trip to Winter Haven. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Chain of Lakes Park

Theatre Winter Haven

You can enjoy a show at Theatre Winter Haven during your trip to Winter Haven. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Theatre Winter Haven

Frequently asked questions

How do I find cheap flights to Winter Haven that have flexible change policies?
When it comes to flying these days, flexibility is important. That's why we've added a "No change fee" search function to help you find flexible and cheap flights to Winter Haven. It's to the left of your screen directly underneath the "Flexible change policies" heading.
Which airlines fly to Winter Haven?
Grab your passport and suitcase and jump on board one of these two airlines that service Winter Haven:

  • American Airlines - 2,808 flights to or near Winter Haven each month, including 1,538 flights to Orlando Intl. Airport (MCO) and 1,269 to Tampa Intl. Airport (TPA) per month.
  • Spirit Airlines - 2,363 flights to or near Winter Haven each month, including 1,929 flights to Orlando Intl. Airport (MCO) and 433 to Tampa Intl. Airport (TPA) per month.

How can I find cheap tickets to Winter Haven?
A great strategy for nabbing cheap airfares is to be flexible with your dates. Begin with searching for your flight to Winter Haven, then click on the "flexible dates" box for a list of prices for nearby days. Another good tip? Book well ahead. To give you an idea of fares, was the lowest price for a flight to Winter Haven in the last seven days.
How much is a flight to Winter Haven?
In the last seven days, round-trip tickets to Winter Haven sold for as low as and reached a maximum of . For one-way trips taking off from (), the lowest amount paid during this time was .
What are the most popular airports to fly into in Winter Haven?
Choosing the right airport comes down to factors such as your budget and airline. Here are your options in Winter Haven:

  • Orlando Intl. Airport (MCO) - 12,539 flights per month.
  • Tampa Intl. Airport (TPA) - 6,575 flights per month.

When is the cheapest time to fly to Winter Haven?
Try to leave early in the week to secure a bargain airfare to Winter Haven. Tuesday is generally the most affordable day to depart, with Monday right behind it. Saturday often has the highest ticket prices. This is because lots of people choose to begin their vacation on a weekend.
How much is a plane ticket to Winter Haven?
Fares to Winter Haven varied from to in the last seven days. Typically, the quicker you book the better the deal.
What months are the cheapest to book a flight to Winter Haven?
February is the best month to purchase a seat for your Winter Haven trip. Fares are at a premium throughout the festive month of December, so avoid this time if possible.
How long is a flight to Winter Haven?
Your flight to Winter Haven could be short or it could be long depending on where you set off from. Before you load your tablet with movies and audiobooks, check out the average flight times for these top domestic routes:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Orlando Intl. Airport (MCO) - 1 hour and 32 minutes
  • Newark, NJ (EWR-Liberty Intl.) to Orlando Intl. Airport (MCO) - 2 hours and 51 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to Orlando Intl. Airport (MCO) - 2 hours and 27 minutes