Lakeland - Winter Haven Vacation Packages 2026 from $428

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 Fold Hotels Indian Shores

Save 100% on your flight

$428

per person

Nov 7 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,018 reviews)

Such a nice place! Walking distance to the beach. The staff are very friendly and responsive. Our room was very clean and modern. Great stay!!

Reviewed on Sep 10, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,692

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (603 reviews)

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$1,128

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,162 reviews)

Hibiscus Suites - Gateway to Siesta Key

$484

per person

Nov 9 - Nov 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (2,452 reviews)

Reviewed on Sep 30, 2026

voco Sarasota by IHG

Central Sarasota

$532

per person

Nov 9 - Nov 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,000 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

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.

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.

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.

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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A narrow water channel surrounded by lush greenery and tall trees.

Chain of Lakes Park

8.2/10 (185 reviews)

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.

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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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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

$228 nightly

$257 total

Oct 1 - Oct 2

Total with taxes and fees

8/10 Very Good! (10,937 reviews)

"En cuanto me respecta me pareció un lugar bonito, sólo lo ocupamos para dormir claro está porque nos hospedamos con el fin de visitar los parques temáticos de Disney, sólo llegamos a dormir pero tenía lo suficiente y lo necesario para sufrirnos necesidades"

Reviewed on Sep 30, 2026

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

$165 nightly

$188 total

Oct 21 - Oct 22

Total with taxes and fees

8.8/10 Excellent! (3,775 reviews)

"Perfect time to come, it was very quiet and relaxing. All of the staff were so helpful and friendly. The property has everything, you really don’t have to leave."

Reviewed on Sep 30, 2026

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL

Fully refundable

$110 nightly

$123 total

Oct 4 - Oct 5

Total with taxes and fees

9/10 Wonderful! (1,017 reviews)

"Clean room pool area clean. Quick 2 night stay for lacrosse. Plenty of restaurants within a 1/2 mile!"

Reviewed on Sep 30, 2026

See all 45,543 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.