Lakeland - Winter Haven Vacation Packages 2026 from $555

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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.

ChartHouse Clearwater Beach Marina Hotel

$555

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,249 reviews)

The balcony was amazing!!! And room were clean all times.

Reviewed on Jul 25, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$733

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (552 reviews)

The staff was excellent! Our accommodations were very nice, very clean and well maintained. Everything we needed was right at our fingertips during our entire stay.

Reviewed on Jul 23, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$731

per person

Sep 25 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,087 reviews)

Captiva Beach Resort

South Village

Save 100% on your flight

$1,017

per person

Oct 4 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,288 reviews)

Love staying here, the staff is so nice and accommodating to early check-in or late checkout. Always a pleasure.

Reviewed on Jul 24, 2026

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

$755

per person

Oct 4 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (2,374 reviews)

The room was clean and very nice. There was more than enough space for our family that came to visit us. The pool was nice and clean, and the shuttle service they offered was an incredible option if you don't want to drive and park at the beach.

Reviewed on Jul 24, 2026

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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.

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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What to do in Lakeland - Winter Haven

LEGOLAND® Florida Tickets

$39

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

Aug 25 - Aug 26

Total with taxes and fees

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL

Fully refundable

$130 nightly

$146 total

Aug 24 - Aug 25

Total with taxes and fees

8.8/10 Excellent! (3,152 reviews)

"Lazy river is why i booked but we only 2 ft in some spots couldn't even swim and they empied the pool on the saturday night"

Reviewed on Jul 25, 2026

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

Fully refundableReserve now, pay when you stay

$187 nightly

$212 total

Aug 23 - Aug 24

Total with taxes and fees

8.8/10 Excellent! (3,686 reviews)

"Margaritaville Orlando is not a resort, it is a fancy motel at best. Absolutely the WORST experiences I have had at a “resort”…EVER! Let me start with the word resort. I have been all over the country and to other countries and Margaritaville Orlando is NOT a resort. At best it is a fancy motel with ..."

Reviewed on Jul 25, 2026

See all 44,550 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.