Lakeland - Winter Haven Vacation Packages 2026 from $890

Photo by Lakeland Convention and Visitors Bureau

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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 Center and Lakeside Village. Davenport is another city that draws travelers 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.

The Latest Lakeland - Winter Haven vacation packages

Price found within the past 48 hours. Click for updated prices.

The Avalon Club

Save 100% on your flight

$890

per person

Dec 12 - Dec 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (608 reviews)

Great place to stay with the family. Rooms were clean and spacious. Parking was easy. Walkable to many stores and restaurants. Very close to the beach, and the hotel has everything needed for your beach day: towels, chairs, umbrellas, floaties, and sand toys.

Reviewed on Oct 7, 2026

Stylish Treasure Island Escape

Sunshine Beach

Save 100% on your flight

$4,956

per person

Dec 22 - Dec 28

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

No reviews

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,172

per person

Dec 22 - Dec 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (604 reviews)

So clean and anything at all that we needed the staff was more than willing to do great experience

Reviewed on Oct 4, 2026

BeachTrail Lodging

Save 100% on your flight

$1,221

per person

Dec 25 - Dec 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (101 reviews)

The cottage was well stocked with a snack basket and a super dog basket. The kitchen was stocked with all needed essentials and the parking also worked out well.

Reviewed on Apr 14, 2026

The Hotel Zamora

Save 100% on your flight

$981

per person

Dec 12 - Dec 19

found 20 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (423 reviews)

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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

A garden with a central fountain, surrounded by white columns and covered walkways.

Lake Hollingsworth

If you're spending some time in Lake Hollingsworth, Lake Hollingsworth and Beerman Family Tennis Center are top sights worth seeing.

A calm lake with lily pads, surrounded by a park with palm trees and buildings.

Downtown Lakeland

1 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.

A crocodile resting on a log near a body of water with greenery around.

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.

A circular fountain with a statue in the center, surrounded by palm trees and a building with a red roof in the background.

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 Otis M. Andrews Sports Complex.

Stay near popular Lakeland - Winter Haven attractions

The entrance to LEGO Florida with colorful LEGO structures and a large LEGO sign.

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.

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A lakeside park with a walking path, palm trees, and a dock extending into the water.

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.

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A wooden boardwalk leading to a sign that reads "Deinonychus Island."

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.

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A large aircraft with a red nose and four propellers, mounted on a white structure.

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.

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A historic tower with intricate designs, surrounded by lush greenery and a clear blue sky.

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.

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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.

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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.

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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.

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What to do in Lakeland - Winter Haven

LEGOLAND® Florida Tickets

$33

per traveler

86% of travellers recommend

LEGOLAND Florida FasTrack Pass

$87

per traveler

Wild Dolphin Exploration Boat Ride and Clearwater Beach Day

$129

per adult

90% of travellers recommend

See all activities in 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

$219 nightly

$246 total

Nov 9 - Nov 10

Total with taxes and fees

8/10 Very Good! (10,908 reviews)

"The property and room were beautiful and well maintained. The kids had a great time. So much for them to do. The pools are amazing."

Reviewed on Oct 10, 2026

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

$177 nightly

$201 total

Nov 1 - Nov 2

Total with taxes and fees

8.8/10 Excellent! (3,784 reviews)

"It was actually pretty awesome"

Reviewed on Oct 9, 2026

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

Fully refundableReserve now, pay when you stay

$116 nightly

$132 total

Oct 18 - Oct 19

Total with taxes and fees

9/10 Wonderful! (4,811 reviews)

"Large facility with great pool."

Reviewed on Oct 10, 2026

See all 45,381 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.