Winter Haven Vacations

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Find the Best Winter Haven Vacation Packages

Winter Haven Hotel Deals

Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
Fully refundableReserve now, pay when you stay
The price is AED 375 per night from Feb 11 to Feb 12
AED 375
AED 420 total
11 Feb - 12 Feb
includes taxes & fees
7/10 Good! (1,005 reviews)
Kind and helpful staff. Clean room.

Reviewed on 31 January 2026

Howard Johnson by Wyndham Winter Haven FL
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
The price is AED 859 per night from Feb 27 to Feb 28
AED 859
AED 1,107 total
27 Feb - 28 Feb
includes taxes & fees
9/10 Wonderful! (159 reviews)
Good

Reviewed on 2 February 2026

LEGOLAND Beach Retreat
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
The price is AED 1,135 per night from Mar 1 to Mar 2
AED 1,135
AED 1,415 total
1 Mar - 2 Mar
includes taxes & fees
8.8/10 Excellent! (66 reviews)
Room clean kids loved bunkbeds Staff helpful

Reviewed on 1 February 2026

Legoland Florida Hotel
See all 39,303 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

Explore miniature cityscapes at LEGOLAND Florida in Winter Haven with detailed architectural models

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
Scenic view of Winter Park, Chain of Lakes canal. The Chain of Lakes is a popular tourist destination for residents and visitors to Winter Park, Florida, USA.

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
Sunrise at Rotary Riverfront Park, Titusville, Florida

Rotary Park

Rotary 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.

Rotary Park

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