Lakeland - Winter Haven Vacation Packages 2026 from $724

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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.

Ocean Club Treasure Island Hotel

Sunshine Beach

$724

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,096 reviews)

Rooms were very clean parking was great. We loved our trip and we will go back again, it was wonderful,

Reviewed on Jul 27, 2026

Resort Sixty-Six

Save 100% on your flight

$789

per person

Oct 17 - Oct 24

found 6 hours ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

9/10 Wonderful! (8 reviews)

Cedar Cove Resort and Cottages

Save 100% on your flight

$904

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (561 reviews)

Everything was amazing from the moment I walked in to the office for check in, the staff was friendly, helpful and informative! This was a home away from home! I will definitely be back next year!

Reviewed on Jul 26, 2026

CW Hotel

Save 100% on your flight

$768

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (16 reviews)

We were on the 7th floor in a suite with a wrap around balcony and we could see the bay and the ocean. It was a easy 5 min walk to the Clearwater beach. Great location, great room and good food at the hotel. We will definitely be coming back.

Reviewed on Jul 27, 2026

The Avalon Club

Save 100% on your flight

$1,359

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (569 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.

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

$228 nightly

$256 total

Aug 24 - Aug 25

Total with taxes and fees

8/10 Very Good! (10,585 reviews)

"This was our second time staying at the grove really nice property amenities are excellent. There are stores and restaurants close by. Food at the hotel is great too. And staff is very friendly and helpful."

Reviewed on Jul 28, 2026

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL

Fully refundable

$141 nightly

$158 total

Aug 23 - Aug 24

Total with taxes and fees

8.8/10 Excellent! (3,171 reviews)

"Good for short stay"

Reviewed on Jul 28, 2026

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

$191 nightly

$217 total

Aug 19 - Aug 20

Total with taxes and fees

8.8/10 Excellent! (3,706 reviews)

"The staff was great very helpful .Pool nice vibe whole place just beautiful we definitely returning !"

Reviewed on Jul 28, 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.