Lakeland - Winter Haven Vacation Packages 2026 from $462

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.

voco Sarasota by IHG

Central Sarasota

$462

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,007 reviews)

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,175

per person

Oct 23 - Oct 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (568 reviews)

Very charming small hotel, staff was extremely helpful, rooms were clean and had everything we needed for our stay. 10/10 will definitely stay there again

Reviewed on Aug 11, 2026

The Westin Sarasota

Central Sarasota

$847

per person

Oct 17 - Oct 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,151 reviews)

Had a wonderful experience, convenient location

Reviewed on Aug 12, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$806

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,128 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 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 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 Veterans Park 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 Family Fun Center and The Club at Eaglebrooke, 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 Plant City Tennis Center.

Stay near popular Lakeland - Winter Haven attractions

A detailed model of a cityscape with various buildings, including a tall skyscraper, a modern building, and a historic building with a red roof.

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 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 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 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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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

$35

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

$218 nightly

$245 total

Aug 24 - Aug 25

Total with taxes and fees

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

$187 nightly

$212 total

Aug 24 - Aug 25

Total with taxes and fees

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL

Fully refundableReserve now, pay when you stay

$172 nightly

$194 total

Sep 1 - Sep 2

Total with taxes and fees

8.8/10 Excellent! (3,228 reviews)

"The property is HUGE! Lots to do, many walking trails and the lazy river was such a hit with the kids. There are amenities where you need to pay extra, $20 for a day wristband and $7 for a donut float (for the river). We had an incident where a deposit was charged twice but the staff was helpful ..."

Reviewed on Aug 12, 2026

See all 44,468 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.