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.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was CA $1,137, price is now CA $779 per person
CA $779
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,002 reviews)
Great staff at the desk. Tiffany was great! Room was very modern. WiFi was mostly good. Location was central to downtown within walking distance of restaurants and cafes. Nice walking trail down by the water, too.

Reviewed on Apr 21, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,890, price is now CA $1,931 per person
CA $1,931
per person
Jun 20 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (531 reviews)
It was actually perfect. Amazing beach, amazing spacious room. One of our new top picks for vacay spots.

Reviewed on Apr 30, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $1,832, price is now CA $1,236 per person
CA $1,236
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (503 reviews)
We loved this hotel for a family trip. The beach is literally just steps away, which made everything so convenient. Everything was clean, the staff was good, and there are plenty of nearby restaurants.

Reviewed on Apr 24, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was CA $1,474, price is now CA $1,028 per person
CA $1,028
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,002 reviews)
Property is definitely in need for update. Location is great and staff is Friendly

Reviewed on Apr 29, 2026

Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Belle Vista
Price was CA $1,463, price is now CA $1,033 per person
CA $1,033
per person
Jun 9 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.4/10 Very Good! (531 reviews)
This is a quiet property

Reviewed on Apr 1, 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
Downtown Lakeland

Downtown Lakeland

1 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 $226 per night from May 7 to May 8
CA $226
per night
May 7 - May 8
8/10 Very Good! (9,695 reviews)
The hallways were never vacuumed. The sliding door to the balcony was broken. The doors to the master bath wouldn’t close. The toilet in the second bath wouldn’t flush. No hand soap in the bathrooms. We had to ask for enough bath towels for each guest in the room multiple times. Mattresses are very ...

Reviewed on Apr 30, 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
The price is CA $177 per night from May 12 to May 13
CA $177
per night
May 12 - May 13
8.8/10 Excellent! (3,586 reviews)
As soon as I walked in to my room, I called the front desk. I requested that Sean someone to place the two very heavy closet doors back in their tracks so we can use the closet. They never sent anyone. We had to hang our clothes around the room. Some areas in the walkways had missing stone work. ...

Reviewed on Apr 30, 2026

Margaritaville Resort Orlando with H2O Waterpark
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
7700 Westgate Blvd. Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from May 3 to May 4
CA $124
per night
May 3 - May 4
8.2/10 Very Good! (1,662 reviews)
very clean

Reviewed on Apr 30, 2026

Westgate Town Center Resort
See all 45,190 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.
All Inclusive Vacations
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Beach Vacations
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Family Vacations
Family Vacations

Discover the most popular places to visit in Lakeland - Winter Haven

LEGOLAND® Florida

LEGOLAND® Florida

4.5/5(73 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

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 $53
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

CA $259
per adult
96% of travellers recommend
Walt Disney World® Resort Theme Park Tickets
Scenic One Hour Airboat Tour

Boggy Creek Scenic Everglades Airboat Tour

CA $61
per adult
98% of travellers recommend
Boggy Creek Scenic Everglades Airboat Tour
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.