Lakeland - Winter Haven Vacation Packages

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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 Centre and Lakeside Village. Davenport is another city that draws travellers 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.

Top Lakeland - Winter Haven Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,280, price is now CA $754 per person
CA $754
per person
Apr 30 - May 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.6/10 Excellent! (68 reviews)
Staff was very responsive although we did not meet in person. Very old but clean Florida Motel which is all we needed for the night and the price was good!

Reviewed on Feb 26, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,923, price is now CA $1,797 per person
CA $1,797
per person
Apr 26 - May 2
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.4/10 Exceptional! (515 reviews)
There was absolutely No view. Honestly not sure why that room has a balcony. Your view is of a side of a wall directly across from you. Otherwise, room was great! Clean, roomy, and all needs met.

Reviewed on Mar 11, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was CA $2,091, price is now CA $1,384 per person
CA $1,384
per person
Apr 21 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
9/10 Wonderful! (1,003 reviews)
Nice place to stay- a little pricey for what it is. Decent pool and private beach.

Reviewed on Mar 12, 2026

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Price was CA $2,638, price is now CA $1,769 per person
CA $1,769
per person
Apr 21 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
8.4/10 Very Good! (1,666 reviews)
Rumfish was beautiful, we had an ocean view villa with balcony. The staff was friendly, service amazing, and our experience couldn't have beeb better. We will definitely be back.

Reviewed on Mar 12, 2026

Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Price was CA $1,685, price is now CA $1,140 per person
CA $1,140
per person
Apr 21 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Tampa (TPA)
8.6/10 Excellent! (533 reviews)
Room was clean staff was friendly

Reviewed on Mar 11, 2026

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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
Lakeland Florida Downtown area beautiful and peaceful

Downtown Lakeland

2 out of top 10 points of interest in this area
5/5(1 area review)

If you're spending some time in Downtown Lakeland, Polk Theatre and RP Funding Center are top sights worth seeing.

Find hotels in Downtown Lakeland

Ready to book your vacation to Lakeland - Winter Haven?

 

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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
The price is CA $244 per night from Apr 13 to Apr 14
CA $244
CA $350 total
Apr 13 - Apr 14
includes taxes & fees
8/10 Very Good! (9,109 reviews)
We loved the pool..

Reviewed on Mar 13, 2026

The Grove Resort & Water Park Orlando
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4 out of 5
8505 W Irlo Bronson Memorial Hwy Kissimmee FL
Fully refundable
The price is CA $194 per night from Apr 13 to Apr 14
CA $194
CA $278 total
Apr 13 - Apr 14
includes taxes & fees
8.8/10 Excellent! (2,695 reviews)
I booked through Expedia, when i got there, they didn’t have my reservation showing in there end, I had to wait until they put me in the system, after a long day with two kids it was not good check in. The pools were really nice and outside everything was good، but the room was old and not clean ...

Reviewed on Mar 13, 2026

Holiday Inn Club Vacations at Orange Lake Resort by IHG
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
7700 Westgate Blvd. Kissimmee FL
The price is CA $134 per night from Apr 12 to Apr 13
CA $134
CA $199 total
Apr 12 - Apr 13
includes taxes & fees
8/10 Very Good! (1,498 reviews)
We chose this resort because it was dog friendly and had plenty of amenities. It did not disappoint. There is plenty to do without leaving the resort. The building we were in was a little old but close to a pool so that was ok. We wish the mini golf stayed open later. Overall loved it and would stay ...

Reviewed on Mar 12, 2026

Westgate Town Center Resort
See all 45,172 properties in Lakeland - 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.
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Discover the most popular places to visit in Lakeland - Winter Haven

Legoland Florida featuring a pond, a garden and a river or creek

LEGOLAND® Florida

4.5/5(72 reviews)

Take the kids to this dynamic theme park for a day full of exciting rides, LEGO® brick creations and the chance to build your own LEGO®robots.

LEGOLAND® Florida
Dinosaur World Museum

Dinosaur World

5/5(1 review)

With more than 200 life-size dinosaur models and many interactive games and activities, this educational theme park is great for families.

Dinosaur World
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

3/5(1 review)

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

What to do in Lakeland - Winter Haven

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $86
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Scenic One Hour Airboat Tour

Boggy Creek Scenic Everglades Airboat Tour

CA $60
per adult
98% of travellers recommend
Boggy Creek Scenic Everglades Airboat Tour
Flagler College in St. Augustine.

Historic St. Augustine Day Trip from Orlando with Hotel Pickup

CA $137
per adult
82% of travellers recommend
Historic St. Augustine Day Trip from Orlando with Hotel Pickup
See all activities in Lakeland - Winter Haven

Frequently asked questions

Can I cancel my flight booking to Lakeland - Winter Haven due to COVID-19?
Our handy Customer Service Portal is your one-stop shop for most travel questions, including about flight changes due to COVID-19. For extra peace of mind, we suggest looking over the terms and conditions of your preferred carrier before reserving your tickets.
What's the best way to find cheap flights to Lakeland - Winter Haven that have flexible change policies?
It's as easy as counting 1-2-3 with Expedia. Firstly, enter your preferred dates and destination and click on "Search." Next step? Check "No change fee" just below the "Flexible change policies" subheading on the left-hand side of your screen. Step 3. Book a cheap and flexible ticket to Lakeland - Winter Haven.
What are some of the general tips for travelers to Lakeland - Winter Haven during the COVID-19 outbreak?
The COVID-19 pandemic has brought about substantial changes to how we travel. If you're planning a vacation in Lakeland - Winter Haven, the following tips will help you navigate this new traveling reality:
  • Understand the rules and restrictions in both your destination and origin. You may not be able to travel depending on local circumstances, so don't forget to check before you book your flight.
  • You must wear a face mask at the airport, including at screening checkpoints. Be prepared to lower your mask for ID verification when asked by a TSA officer.
  • Instead of handing a TSA employee your boarding pass, place it directly on the scanner yourself. When that's done, hold it up for inspection.
  • One container of liquid hand sanitizer is now allowed in your carry-on baggage. It must not be larger than 12 oz (350 ml), and you'll have to take it out of your bag for X-ray screening.
  • Put any personal items (keys, wallet and phone) in your carry-on instead of a bin to reduce handling during the screening process.
  • Transport any food items in a clear plastic bag and also put them in a screening bin. Separating food from your carry-on means it's less likely a TSA agent will need to open your bag for inspection.

Which airlines fly to Lakeland - Winter Haven?
Lock in your fare with Delta and then start organizing your Lakeland - Winter Haven to-do list. This popular airline has 1472 flights each month to Orlando Intl. Airport (MCO), a central gateway.
How can I find cheap tickets to Lakeland - Winter Haven?
For an unbeatable deal to Lakeland - Winter Haven, book well ahead. Also take advantage of Expedia's handy "flexible dates" feature above your search results. This will compare the cheapest prices for similar time frames. In the last seven days, was the best price for a flight to Lakeland - Winter Haven.
How much is a flight to Lakeland - Winter Haven?
There were plenty of bargain fares up for grabs in the last seven days, with the price of a return ticket to Lakeland - Winter Haven ranging between and . Many lucky vacationers nabbed one-way seats from () for just .
What are the most popular airports to fly into in Lakeland - Winter Haven?
Zip up your suitcase and jet into Orlando Intl. Airport (MCO), Lakeland - Winter Haven's major flight hub. Book a seat on one of the 13460 flights that land at this awesome destination each month.
When is the cheapest time to fly to Lakeland - Winter Haven?
Flying on a Tuesday, followed by a Monday, is generally the best way to get the cheapest fare. Steer clear of weekends if possible, because Saturday is typically the most expensive day. Spend the dollars you saved having a ball in Lakeland - Winter Haven instead!
How much is a plane ticket to Lakeland - Winter Haven?
Flights to Lakeland - Winter Haven ranged from to in the last seven days. Normally, the sooner you book the bigger the bargain.
Which airlines with flights to Lakeland - Winter Haven employ COVID-19 cleanliness policies?
As passengers take to the skies once again, most commercial airlines have implemented physical distancing and other important actions to help lessen the spread of COVID-19. Here are some great examples:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Spirit Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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