Lakeland - Winter Haven Vacation Packages 2026 from $693

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

Save 100% on your flight

$693

per person

Oct 20 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,000 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$756

per person

Oct 6 - Oct 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,173 reviews)

Super clean, beautiful unit! The staff was absolutely amazing and courteous at every turn. We found our home when we are in the area.

Reviewed on Sep 1, 2026

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$816

per person

Oct 20 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,160 reviews)

This hotel has a great location. The staff is so nice they care you and go through all the details that makes you feel like home. The only thing was the breakfast that we found the bread wasn't fresh, the eggs tasted like boxed frozen food . The service was nice but too slow and meals were cold. I would recommend this hotel but please pay attention to the breakfast service! and thr service was too slow

Reviewed on Aug 31, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,548

per person

Oct 2 - Oct 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (584 reviews)

Tropical Beach Resorts

South Village

Save 100% on your flight

$912

per person

Oct 20 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (5,792 reviews)

everything we needed was walking distance from our room. Very convenient

Reviewed on Sep 2, 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

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 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 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 Polk Museum of Art and Lake Mirror.

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 wooden boardwalk by a lake with trees and a bench.

Dixieland

While there might not be top attractions in Dixieland, you can explore the larger area and discover places like RP Funding Center and Polk Museum of Art.

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 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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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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Southern Dunes Golf and Country Club

7.8/10 (15 reviews)

Enjoy a round of golf in Haines City at Southern Dunes Golf and Country Club. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

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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

Sep 8 - Sep 9

Total with taxes and fees

8/10 Very Good! (10,789 reviews)

"This trip was excellent. The hotel had everything there for family fun. Hey literally try to ensure that there is something for everyone to do. You never have to leave the property."

Reviewed on Sep 2, 2026

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

$187 nightly

$212 total

Sep 9 - Sep 10

Total with taxes and fees

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

Fully refundableReserve now, pay when you stay

$116 nightly

$132 total

Sep 14 - Sep 15

Total with taxes and fees

9/10 Wonderful! (4,760 reviews)

"Excelente"

Reviewed on Sep 2, 2026

See all 44,960 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.