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.
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Price was CA $2,025, price is now CA $1,343 per person
CA $1,343
per person
Apr 17 - Apr 24
found 13 hours ago
Roundtrip flight included
Halifax (YHZ) to Tampa (TPA)
8.6/10 Excellent! (496 reviews)
The room was clean. Comfortable bed. Kitchenette. Beautiful view of the water. Can watch the birds. Close to stores, restaurant, St. Pete beach, Tampa bay, and old Tampa bay, and other sites. The city of St. Petersburg and Tampa.

Reviewed on Jan 24, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $3,218, price is now CA $2,010 per person
CA $2,010
per person
Apr 17 - Apr 24
found 13 hours ago
Roundtrip flight included
Halifax (YHZ) to Tampa (TPA)
9.2/10 Wonderful! (1,097 reviews)
Great overall. The housekeeping is always behind but you just have to call multiple times.

Reviewed on Feb 4, 2026

John's Pass Hotel

John's Pass Hotel

2 out of 5
Price was CA $3,037, price is now CA $1,950 per person
CA $1,950
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (263 reviews)
Room was spotless. Great stay here. Great for a couple days vacation with enough to walk to including the beach. Will come back again.

Reviewed on Feb 3, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,812, price is now CA $1,824 per person
CA $1,824
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Wonderful staff and facilities. Rooms were spacious, clean, and quiet. Staff was very attentive to the needs of guests and were the best! Would highly recommend a stay here. We were first-time guests, and plan to stay here again when we return to Clearwater Beach.

Reviewed on Jan 31, 2026

Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Sunshine Beach
Price was CA $2,869, price is now CA $1,865 per person
CA $1,865
per person
Apr 17 - Apr 24
found 13 hours ago
Roundtrip flight included
Halifax (YHZ) to Tampa (TPA)
8.8/10 Excellent! (2,355 reviews)
Furniture was very old/ dirty and couch was broken.

Reviewed on Jan 14, 2026

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

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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 $217 per night from Feb 9 to Feb 10
CA $217
CA $320 total
Feb 9 - Feb 10
includes taxes & fees
8/10 Very Good! (9,022 reviews)
Great service and the place was so clean!! I would stay again. And they upgraded our room from a two-bedroom to a three-bedroom condo!

Reviewed on Feb 5, 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 $204 per night from Feb 9 to Feb 10
CA $204
CA $289 total
Feb 9 - Feb 10
includes taxes & fees
8.6/10 Excellent! (2,604 reviews)
A door from the bedroom to the living room squeaked loudly. If they missed that, made you wonder other things they missed

Reviewed on Feb 5, 2026

Holiday Inn Club Vacations at Orange Lake Resort by IHG
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

4 out of 5
7600 Mystic Dunes Lane Kissimmee FL
The price is CA $145 per night from Feb 24 to Feb 25
CA $145
CA $211 total
Feb 24 - Feb 25
includes taxes & fees
9/10 Wonderful! (4,660 reviews)
Room was clean and well furnished....

Reviewed on Feb 6, 2026

Hilton Vacation Club Mystic Dunes Orlando
See all 45,791 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

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
Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

CA $145
per traveller
80% of travellers recommend
Two Flight Indoor Skydiving Experience
Swimming manatees in Orlando.

From Orlando: Manatees Swim, Snorkel and Boat Day Tour with Hotel Pickup

CA $235
per adult
98% of travellers recommend
From Orlando: Manatees Swim, Snorkel and Boat Day Tour 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.