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 $1,631, price is now CA $1,076 per person
CA $1,076
per person
Apr 26 - May 3
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
8.6/10 Excellent! (68 reviews)
The property was perfect for pets. Big space to walk and off the main road.

Reviewed on Mar 23, 2026

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was CA $1,742, price is now CA $1,131 per person
CA $1,131
per person
May 9 - May 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
7.4/10 Good! (27 reviews)
This resort is absolutely amazing I didn't eat breakfast there but I'm sure it was awesome because everything else there was awesome

Reviewed on Mar 16, 2026

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Town 'n' Country
Price was CA $1,969, price is now CA $1,318 per person
CA $1,318
per person
May 9 - May 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
2/10 (4 reviews)
The Avalon Club

The Avalon Club

4 out of 5
Price was CA $3,005, price is now CA $2,018 per person
CA $2,018
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (515 reviews)
Our family had a wonderful 4-night stay at this well kept hotel. The apartment was spacious, very clean, had nice amenities, and the hotel is conveniently located just steps from the beach. We recommend and would be happy to stay there again.

Reviewed on Mar 13, 2026

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Price was CA $1,673, price is now CA $1,134 per person
CA $1,134
per person
May 4 - May 11
found 4 hours ago
Roundtrip flight included
Hamilton (YHM) to Tampa (TPA)
8.6/10 Excellent! (2,526 reviews)
Clean room, gave us a riverview, staff was friendly

Reviewed on Mar 26, 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

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, RP Funding Center and Lake Mirror 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
The price is CA $261 per night from Apr 12 to Apr 13
CA $261
CA $370 total
Apr 12 - Apr 13
includes taxes & fees
8/10 Very Good! (9,264 reviews)
Room wasn’t clean upon arrival. Cabinet doors were hanging crooked . Kitchen wasn’t stocked with proper utensils, cooking related pots/pans etc. the pool and lazy river were both quite nice.

Reviewed on Mar 26, 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 $227 per night from Apr 13 to Apr 14
CA $227
CA $316 total
Apr 13 - Apr 14
includes taxes & fees
8.8/10 Excellent! (2,733 reviews)
Very child friendly

Reviewed on Mar 25, 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 $136 per night from Apr 12 to Apr 13
CA $136
CA $202 total
Apr 12 - Apr 13
includes taxes & fees
8.2/10 Very Good! (1,532 reviews)
Not impress with the staff regarding them trying to sell me one of there timeshares however since I don't have a husband I didn't qualify for the gifts. Single mothers are very successful on there own and don't always need a man. So being judged by that did not sit well.

Reviewed on Mar 26, 2026

Westgate Town Center Resort
See all 45,208 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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

LEGOLAND® Florida

LEGOLAND® Florida

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

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

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
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
Scenic 30 Minute Airboat Tour

Scenic 30 Minute Airboat Tour

CA $60
per adult
100% of travellers recommend
Scenic 30 Minute 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.