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.
ChartHouse Clearwater Beach Marina Hotel
CA $1,481
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
9.6/10 Exceptional! (1,341 reviews)
Loved our stay!!! Room was amazing with huge balcony looking over the pool area! We loved the pool with a fantastic view of the marina! Would definitely recommend this hotel!
Reviewed on Aug 10, 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
2 out of top 10 points of interest in this area
If you're spending some time in Downtown Lakeland, Polk Theatre and RP Funding Center are top sights worth seeing.
Lake Hollingsworth
If you're spending some time in Lake Hollingsworth, Lake Hollingsworth and Veterans Park are top sights worth seeing.
Lakeland Highlands
When in Lakeland Highlands, you can plan a visit to Family Fun Center and The Club at Eaglebrooke, some noteworthy sights in the nearby area.
South Lake Morton
If you're looking for some top things to see and do in South Lake Morton and surrounding area, you can visit Lake Mirror and Polk Theatre.
Downtown
If you're looking for some top things to see and do in Downtown and surrounding area, you can visit Robert W. Willaford Railroad Museum and Plant City Tennis Center.
Ready to book your vacation to Lakeland - Winter Haven?
Lakeland - Winter Haven Hotel Deals
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
CA $236
CA $342 total
Aug 25 - Aug 26
includes taxes & fees
Margaritaville Resort Orlando with H2O Waterpark
8000 Fins Up Circle Kissimmee FL
Fully refundableReserve now, pay when you stay
CA $194
CA $296 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (3,755 reviews)
"Staff made it amazing. Was great and beautiful. Had great time with my wife and enjoyed every minute"
Reviewed on Aug 10, 2026
Holiday Inn Club Vacations at Orange Lake Resort by IHG
8505 W Irlo Bronson Memorial Hwy Kissimmee FL
Fully refundable
CA $177
CA $270 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (3,218 reviews)
"Long lines to check in, room cards won't be activated until you are presented a timeshare sales pitch and have to say no three times. Salesperson immediately changed his attitude knowing that he wasn't going to get a sale., immediately turned rude. Property is nice, most likely won't stay here ..."
Reviewed on Aug 10, 2026
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.
Stay near popular Lakeland - Winter Haven attractions
LEGOLAND® Florida
9.0/10 (2,150 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.
Dinosaur World
8.6/10 (65 reviews)
With more than 200 life-size dinosaur models and many interactive games and activities, this educational theme park is great for families.
Lakeside Village
7.8/10 (443 reviews)
You can search for that perfect souvenir at Lakeside Village during your visit to Lakeland. Amble around the area's lakeside or attend a sporting event.
Photo by throwingsofas
Bok Tower Gardens
9.0/10 (158 reviews)
Bok Tower Gardens is just one of the places to see in Lake Wales, so why not enjoy the other things to explore during your travels? Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
Photo by Rachel Graves
Lake Mirror
8.2/10 (242 reviews)
Commune with nature and explore the great outdoors at Lake Mirror during your travels in Lakeland. Stroll along the lakeside or attend a sporting event in this family-friendly area.
RP Funding Center
7.6/10 (545 reviews)
You can make plans for a show at RP Funding Center on your trip to Lakeland. Amble around the area's lakeside or attend a sporting event.
Publix Field at Joker Marchant Stadium
7.8/10 (448 reviews)
Catch an event at Publix Field at Joker Marchant Stadium during your trip to Lakeland. Stroll along the lakeside or attend a sporting event in this family-friendly area.
Lakeland Square Mall
7.8/10 (576 reviews)
You can search for that perfect souvenir at Lakeland Square Mall during your stay in Lakeland. Amble around this family-friendly area's lakeside or attend a sporting event.
What to do in Lakeland - Winter Haven
Boggy Creek Scenic Everglades Airboat Tour
CA $62
per adult
98% of travellers recommend
From Orlando: Manatees Swim, Snorkel and Boat Day Tour with Hotel Pickup
CA $225
per adult
98% of travellers recommend
Frequently asked questions
How much does a Lakeland - Winter Haven vacation package cost?
Custom build your Lakeland - Winter Haven package from as little as CA $872. Pick from any combination of rental cars, flights and hotels to craft the getaway of your dreams. Don't forget to add on a few experiences or tours!
How do I get a cheap travel package to Lakeland - Winter Haven?
Bundle your hotels and flights with Expedia to save big on your next getaway. With more than 550 airlines and 1,000,000 hotel options worldwide, your Lakeland - Winter Haven vacation package can be tailored exactly to suit your travel style. With all that extra money, why not include a few exciting activities and tours? It's an easy way to unlock even more discounts. That vacation you've always dreamed of in Lakeland - Winter Haven is much closer than you thought!
Where should I stay in Lakeland - Winter Haven?
There's an abundance of excellent places to stay in Lakeland - Winter Haven, including Lakeland. This destination is home to many much-loved attractions including Publix Field at Joker Marchant Stadium and Polk Museum of Art. Another option is to head to Winter Haven, where you'll find LEGOLAND® Florida and Chain of Lakes Park. If you're here for a while, journey to both vibrant cities!
What are the top hotels in Lakeland - Winter Haven?
Days Inn & Suites by Wyndham Lakeland and Hyatt Place Lakeland Center know how to make their guests feel welcome in Davenport. If you also plan to get to Haines City, have a look at Comfort Inn & Suites Maingate South and Winter Haven Gardens Inn. Both are popular with travelers.
How far in advance should I book my Lakeland - Winter Haven vacation?
Your best bet is to book early. Airlines typically advertise flight tickets nearly 12 months ahead of departure, and this is a great opportunity to pick up some of the cheapest prices. Just been told you need to take some vacation time next month? No sweat. Expedia are never short on fantastic deals to help you have the getaway of your dreams, at an affordable price.
What does an Expedia Lakeland - Winter Haven travel package include?
Rental cars, flights and hotels — we've got them covered. With Expedia, you can shape your Lakeland - Winter Haven package just the way you want. All you have to do is decide what you need. Once you've made your booking, you can add on fun things like experiences and activities. The more you bundle, the more you save!
What should I know before booking a Lakeland - Winter Haven travel package?
An Expedia travel package can be customized for your budget and is an easy way to stretch your dollars further. How much you include is totally up to you. Hotels, rental cars and flights — decide on a combination that suits your style.
Can I choose my airline with a Lakeland - Winter Haven Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the flexibility to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Lakeland - Winter Haven vacation package?
Whether it's your hotel or flight, you can cancel or alter it. Booked your Lakeland - Winter Haven vacation package in the last 24 hours? You may be able to make changes at no cost. If it's been longer than that, you may be charged a fee by your airline, hotel or car rental company. For further information, head to our Customer Service Portal. We'll help you each step of the way.
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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.
