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
Central Sarasota
CA $1,511
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Tampa (TPA)
9/10 Wonderful! (1,004 reviews)
The hotel is well-located, and well-maintained. The room was clean and spacious. I took advantage of the hotel's relatively small pool, which was fine. The dining area was being renovated, and was only open on weekends (I chose not to dine there). I did not take advantage of the hotel's shuttle to beaches and other nearby amenities. Hotel staff are well-trained and very accommodating. The hotel is walking distance from the commercial area of the downtown, and there are numerous restaurants to choose from. Hotel management, according to staff upon my checkout, apparently would have been gracious in offering to reduce and refund my prepaid reservation by one night of my four night stay due to my airline's extremely delayed plane departure causing a missed airplane connection (and thus a forced overnight stay at the connecting city instead of my reserved day of initial arrival at voco Sarasota). But unfortunately Hotels.Com was unwilling to accommodate my request for the one-night refund.
Reviewed on Sep 13, 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.
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.
Lakeland Highlands
When in Lakeland Highlands, you can plan a visit to The Club at Eaglebrooke and Family Fun Center, some noteworthy sights in the nearby area.
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 Otis M. Andrews Sports Complex.
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 $262
CA $371 total
Oct 1 - Oct 2
includes taxes & fees
8/10 Very good! (10,840 reviews)
"Overall the property was perfect for a large group. There were a few items needed and they were very quick to resolve it. Lots of restaurants about 10-15mins away."
Reviewed on Sep 15, 2026
Margaritaville Resort Orlando with H2O Waterpark
8000 Fins Up Circle Kissimmee FL
CA $193
CA $295 total
Sep 28 - Sep 29
includes taxes & fees
8.8/10 Excellent! (3,790 reviews)
"everything was great ,everything was super clean and well maintained ,staff was very nice and helpfull ,room was beautiful and super clean , pools were clean and well maintained"
Reviewed on Sep 14, 2026
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
CA $146
CA $163 total
Sep 20 - Sep 21
includes taxes & fees
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.
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.
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.
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.
Sun N Fun Air Museum
7.6/10 (272 reviews)
You can spend time browsing the exhibits at Sun N Fun Air Museum during your trip to Lakeland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the 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.
Southern Dunes Golf and Country Club
7.8/10 (15 reviews)
Enjoy a round of golf in Haines City at Southern Dunes Golf and Country Club. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
What to do in Lakeland - Winter Haven
Boggy Creek Scenic Everglades Airboat Tour
CA $61
per adult
98% of travellers recommend
Bonanza Golf & Gifts Entry Ticket in Orlando
CA $25
per adult
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 $1,171. 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.
