Lakeland - Winter Haven Vacations from $651

Book a Hotel + Flight or Car together to unlock savings

Photo by Lakeland Convention and Visitors Bureau
  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Lakeland - Winter Haven Vacation

With everything organized before you go, our Lakeland - Winter Haven vacation packages let you focus on having fun. Known for its golfing, walking trails and family-friendly attractions, the only thing left to do is kick back and enjoy every unforgettable moment. Kick off your trip to Lakeland - Winter Haven with a few nights in Lakeland visiting popular sights like RP Funding Center and Lakeside Village. Davenport is another city that draws travelers from far and wide. Reunion Resort Golf Course and Southern Dunes Golf and Country Club are two of the top places to see here. When it's time to stop dreaming and start packing, Expedia will help turn your Lakeland - Winter Haven vacation into a reality.

The Latest Lakeland - Winter Haven vacation packages

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
ChartHouse Clearwater Beach Marina Hotel
CW Resort
voco Sarasota by IHG
Crystal Palms Beach Resort
Don't see what you're looking for?
See all available trips from Columbus to Lakeland - Winter Haven
View all trips

Where to stay in Lakeland - Winter Haven

Find the best Lakeland - Winter Haven areas and neighborhoods for the activities you enjoy most. Learn more about Lakeland - Winter Haven

Stay near popular Lakeland - Winter Haven attractions

What to do in Lakeland - Winter Haven

Lakeland - Winter Haven Hotel Deals

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $246 total per night from Dec 10 to Dec 11
$246 total
Dec 10 - Dec 11
Total with taxes and fees
8.2/10 Very Good! (10,945 reviews)
"Espectacular"

Reviewed on Nov 10, 2026

The Grove Resort & Water Park Orlando
Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $192 total per night from Nov 29 to Nov 30
$192 total
Nov 29 - Nov 30
Total with taxes and fees
Margaritaville Resort Orlando with H2O Waterpark
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

4 out of 5
7600 Mystic Dunes Lane Kissimmee FL
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $141 total per night from Nov 17 to Nov 18
$141 total
Nov 17 - Nov 18
Total with taxes and fees
9/10 Wonderful! (4,833 reviews)
"Excellent Resort"

Reviewed on Nov 10, 2026

Hilton Vacation Club Mystic Dunes Orlando
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.

Find the Best Lakeland - Winter Haven Vacation Packages

Lakeland - Winter Haven Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Orlando Intl. Airport (MCO)
Population
37,700

More vacations you might like

Frequently asked questions

How do vacation package prices compare across popular destinations in Lakeland - Winter Haven?
Lakeland offers the lowest typical price for a weekend Lakeland - Winter Haven vacation package, while Winter Haven tends to be the highest, with Plant City falling in between. A weekend trip typically costs around $600 per adult in Lakeland, around $750 per adult in Plant City, and around $950 per adult in Winter Haven.

*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.
How can I save money on a Lakeland - Winter Haven vacation package?
When you bundle, you can save up to 30%*. To save money on a Lakeland - 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.
What's included in a Lakeland - Winter Haven vacation package?
A Lakeland - Winter Haven vacation package lets you combine flights, hotel stays, and rental cars, based in one of the region's top destinations like Winter Haven, Lakeland, or Plant City. In Winter Haven, some hotels offer airport shuttle service to and from major hubs like Orlando International Airport (MCO) or Tampa International Airport (TPA), and most hotels include free breakfast. Lakeland also sees most hotels offering airport shuttle service and free breakfast. In Plant City, some hotels provide airport shuttle service, and most include free breakfast.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
Which destinations in Lakeland - Winter Haven offer the best-value vacation package deals?
Lakeland and Plant City are some of the top destinations for cheap Lakeland - Winter Haven vacation package deals. For an affordable weekend getaway, Lakeland is often among the most budget-friendly options, with package prices starting around $320 per adult. For notable bundle savings, Lakeland is also among the best options, with flight-and-hotel bundles saving around $110 per adult for longer stays.

Browse cheap vacation packages in Lakeland - Winter Haven on Expedia to compare 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.
When is the best time to visit the top destinations in Lakeland - Winter Haven?
The best time for a Lakeland - Winter Haven vacation package depends on which destination you choose.

Lakeland sees peak bookings in April, October, and December. October offers average temperatures around 75°F with highs of 84°F, while December is cooler with average temperatures around 64°F and highs of 73°F. If you'd prefer fewer crowds, November and February are quieter, with average temperatures around 68°F and 64°F respectively.

Winter Haven is busiest in March, June, and July. July is the warmest month with average temperatures around 82°F and highs of 90°F, while March is milder with average temperatures around 68°F and highs of 78°F. For a quieter trip, November and January are less crowded, with average temperatures around 68°F and 60°F.

Plant City experiences its peak booking months in March and from December to January. December and January are cooler, with average temperatures around 64°F and 61°F respectively, and highs around 73°F and 70°F. March also brings the Florida Strawberry Festival. If you prefer fewer visitors, July and August are quieter, though warmer, with average temperatures around 82°F and highs of 90°F.
What package types are available across the top destinations in Lakeland - Winter Haven?
Lakeland - Winter Haven, a region known for its family-friendly attractions, offers vacation packages across its key cities like Winter Haven, Lakeland, and Plant City, catering to various travel styles:
  • Budget: In Lakeland, Travelodge by Wyndham Lakeland, rated 8.4 out of 10 by travelers, provides a comfortable stay with free breakfast and an outdoor pool, making it a solid choice for value-focused trips.
  • Breakfast: Winter Haven features options like Staybridge Suites Winter Haven Auburndale by IHG, rated 9.5 out of 10 by travelers, which includes free breakfast and a kitchen in its amenities, with travelers often praising the nice treat of breakfast.
  • Family: For family vacation packages in Lakeland, La Quinta Inn & Suites by Wyndham Lakeland East offers family rooms and a kitchen, and travelers frequently highlight its secure location and good breakfast.
  • Pet-Friendly: In Lakeland, Home2 Suites By Hilton Lakeland North I-4, rated 9.2 out of 10 by travelers, welcomes pets and includes free breakfast and an outdoor pool.
  • Parking: Plant City offers hotels such as TownePlace Suites by Marriott Lakeland, rated 9 out of 10 by travelers, which provides convenient parking and kitchens in its rooms, with travelers noting the great staff and value.
Which destinations should I consider for a Lakeland - Winter Haven vacation?
For a Lakeland - Winter Haven vacation, your choice of base depends on your preferred travel style:
  • Winter Haven: A strong choice for families and those seeking outdoor and adventure activities, with many entertainment options. It is a popular base for vacation packages.
  • Lakeland: Ideal for families and business travelers, offering a mix of family-friendly attractions, outdoor activities, and urban amenities. Vacation packages are readily available here.
  • Plant City: Consider this city for family-friendly attractions and outdoor activities, along with its urban appeal. It also offers vacation packages.
  • Lake Wales: This area is known for its scenic views and outdoor activities, making it a good option for those seeking a romantic getaway or a quieter escape, with a good range of lodging choices.
Is Lakeland - Winter Haven better suited for a beach vacation or a cultural trip?
Lakeland - Winter Haven is primarily an outdoor and nature destination, known for its family-friendly attractions and outdoor activities. The region is dotted with numerous lakes, such as Lake Parker in Lakeland and Crooked Lake near Winter Haven, offering opportunities for water-based recreation and scenic views.

The area excels in entertainment options, including major attractions like LEGOLAND® Florida. For those interested in cultural experiences, places like Bok Tower Gardens in Lake Wales provide beautiful landscapes and historical significance, and the Polk County Historical Museum in Bartow offers local insights.

Overall, Lakeland - Winter Haven is best suited for travelers seeking family fun and outdoor adventures, with cultural sights as a rewarding addition to their trip.
Which airports serve the main destinations in Lakeland - Winter Haven?
For a Lakeland - Winter Haven vacation, the region is primarily served by two major airports. Orlando International Airport (MCO) is a key gateway for travelers, located in Orlando, FL. Another convenient option is Tampa International Airport (TPA), situated in Tampa, FL. Both airports provide access to the various cities within the Lakeland - Winter Haven area.
What are the top things to do across the destinations in Lakeland - Winter Haven?
A Lakeland - Winter Haven vacation offers a variety of attractions spread across its constituent cities, each providing unique experiences:

Browse and book things to do in Lakeland - Winter Haven on Expedia.
Are there family vacation packages in Lakeland - Winter Haven with kid-friendly amenities?
Yes, family vacation packages in Lakeland - Winter Haven offer several options with kid-friendly amenities across its cities:
  • Legoland Florida Hotel: In Winter Haven, this hotel, rated 8 out of 10 by travelers, is designed with families in mind, featuring family rooms and an on-site waterpark, with travelers often impressed by the clean pool.
  • La Quinta Inn & Suites by Wyndham Lakeland East: For family vacation packages in Lakeland, this hotel provides family rooms and kitchens, making it convenient for longer stays, and travelers frequently praise its good breakfast and secure location.
  • Fairfield Inn & Suites by Marriott Lakeland Plant City: In Plant City, this 8-rated hotel by travelers offers family rooms and an outdoor pool, with staff often highlighted for being good and the location convenient.
When should I book vacation packages for the top destinations in Lakeland - Winter Haven?
Booking times for a Lakeland - Winter Haven vacation package vary by destination, with most travelers booking around 2 to 9 weeks before departure.

Travelers tend to book trips to these destinations most often in January, from March to April, from June to July, in October, and in December. If you're planning a spontaneous getaway, Expedia also offers last-minute Lakeland - Winter Haven vacation packages.
How many days do you need for a Lakeland - Winter Haven vacation?
Most Lakeland - Winter Haven vacation packages last around 3 to 7 days, but the ideal trip length depends on where you're going and what you'd like to experience.

Winter Haven, known for its family-friendly attractions and outdoor activities, is often enjoyed over around 3 days, with weekend and week-long stays both popular, allowing time to visit attractions like LEGOLAND® Florida.

Lakeland, offering entertainment and outdoor activities, also typically sees trips of around 3 days, though longer stays are common for those exploring its attractions like the RP Funding Center.

Plant City, with its family-friendly and urban attractions, is also a popular choice for around 3-day trips, with weekend and week-long packages frequently booked, perfect for a visit to Dinosaur World.
Can I change or cancel my Lakeland - Winter Haven vacation package if my plans change?
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.
Do One Key members get extra savings when booking Lakeland - Winter Haven vacation packages?
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.
Does Expedia offer Book Now, Pay Later Lakeland - Winter Haven vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Lakeland - 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.
How do I find last-minute vacation packages to Lakeland - Winter Haven?
To find last-minute vacation packages to Lakeland - 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.
How does free cancellation work on Lakeland - Winter Haven vacation packages?
Free cancellation on a Lakeland - 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.
Is it cheaper to book a Lakeland - Winter Haven vacation as a package or separately?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Lakeland - 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.
Why should I book my Lakeland - Winter Haven vacation package with Expedia?
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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.