Lakeland - Winter Haven Vacation Packages 2026 from $645

Lakeland - Winter Haven flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Cedar Cove Resort and Cottages

$645

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

CW Resort

Save 100% on your flight

$966

per person

Jan 4 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and concierge services.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$709

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.

The Avalon Club

Save 100% on your flight

$1,293

per person

Jan 4 - Jan 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Innisbrook Resort

Save 100% on your flight

$843

per person

Jan 16 - Jan 23

found 19 hours ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

This Tudor resort features a golf course, a full-service spa, and 4 restaurants. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 6 outdoor pools and perks like free WiFi.

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.

See properties

Frequently asked questions

How much are vacation packages to Lakeland - Winter Haven?

Exciting adventures await in Lakeland - Winter Haven, with Travelocity vacation packages starting from as low as $645. In addition to flights and hotels, these amazing deals make it simple to visit more of our wonderful planet.

Where can I get the best vacation package deals for Lakeland - Winter Haven?

It's simple — look no further than Travelocity. With no less than 400 airlines and 1,000,000 properties worldwide, it's easy to put together a Lakeland - Winter Haven package deal that suits your travel style.

Why should I purchase my Lakeland - Winter Haven vacation package with Travelocity?

Because you'll never roam alone if you book through us, and we offer 24/7 customer support and first-rate service to boot. Add to that our Price Match Guarantee and countless destinations and experiences to select from. We're here to help you have the trip of a lifetime.

Can I save money on my Lakeland - Winter Haven car rental if I combine it with my hotel or flight?

Absolutely. And our Lakeland - Winter Haven vacation packages are the ideal way to do it. With just a few clicks you can save money and time by booking everything in one place. Pick up the keys to your rental car then set your own course. Looking for things to do? Add some tours or experiences to your package and save on those too.

Which airport is best for Lakeland - Winter Haven?

Most visitors come to Lakeland - Winter Haven via Orlando Intl. Airport (MCO) or Tampa Intl. Airport (TPA). St. Petersburg-Clearwater Intl. Airport (PIE) is also popular.

What is there to do in Lakeland - Winter Haven?

Lakeland - Winter Haven is full of fabulous photo-ops, however LEGOLAND® Florida and Publix Field at Joker Marchant Stadium are two favorites.

Where to stay in Lakeland - Winter Haven: Best areas for travelers

Cypress Gardens: If you enjoy staying close to the action, look no further than this neighborhood. There is so much to discover here, such as Legoland Florida. The Econo Lodge, the Rodeway Inn & Suites Winter Haven at Chain of Lakes and the Hilton Garden Inn Destin will have a cozy room for you when the day is done.
Downtown: If you're a first-time visitor to this city, this neighborhood is a great choice. Not only are there lots of hotels to select from, there are also renowned attractions like Polk Museum of Art to keep you entertained. Explore all this area has to offer from the convenience of The Terrace Hotel, the Hyatt Place Lakeland Center or the Springhill Stes Lakel Marriott.