Lakeland - Winter Haven Vacation Packages 2026 from $744

Lakeland - Winter Haven flight + hotel vacation packages

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

Crystal Palms Beach Resort

Sunshine Beach

$744

per person

Jan 28 - Feb 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features an outdoor pool and a hot tub. Dry cleaning, laundry facilities, and barbecue grills are also on offer.

ChartHouse Clearwater Beach Marina Hotel

$751

per person

Jan 18 - Jan 25

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 24-hour gym and perks like free WiFi. A rooftop terrace is on site, and self parking and a 24-hour front desk are also offered.

Ocean Club Treasure Island Hotel

Sunshine Beach

$1,047

per person

Feb 5 - Feb 9

found 22 hours 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.

Westwinds Waterfront Resort

$820

per person

Feb 5 - Feb 9

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. A picnic area, express check-out, and barbecue grills are also on offer.

FUSION Resort Waterfront Suites

$838

per person

Feb 5 - Feb 9

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and perks like free self parking and free WiFi. A computer station, luggage storage, and concierge services are also on offer.

Top Lakeland - Winter Haven hotels deals

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$222 nightly

$250 total

Dec 7 - Dec 8

Total with taxes and fees

Free water park access, 3 restaurants, and 6 outdoor pools are all featured at this resort. Bring the family and enjoy the lazy river, children's club, and mini golf. Enjoy the 2 hot tubs and perks like free WiFi.

Pool

Hot Tub

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$201 total

Nov 29 - Nov 30

Total with taxes and fees

This smoke-free resort features free water park access, a full-service spa, and 3 restaurants. Bring the family and enjoy the lazy river, waterslide, and arcade/game room. Enjoy the 3 outdoor pools and perks like free WiFi.

Pool

Hot Tub

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$141 total

Nov 18 - Nov 19

Total with taxes and fees

A golf course, 4 outdoor pools, and 2 outdoor tennis courts are all featured at this smoke-free hotel. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Pool

Free WiFi

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL

Free Cancellation

$148 nightly

$167 total

Nov 29 - Nov 30

Total with taxes and fees

This traditional resort features a golf course, free water park access, and 9 restaurants. There's fun for all ages with a lazy river and a children's club, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free self parking.

Pool

Hot Tub

Omni Orlando Resort at ChampionsGate

1500 Masters Blvd Davenport FL

Free Cancellation

Reserve now, pay when you stay

$233 nightly

$265 total

Nov 29 - Nov 30

Total with taxes and fees

This hotel features a golf course, free water park access, and a full-service spa. Bring the family and enjoy the lazy river, children's club, and mini golf. Enjoy a meal in one of the 10 restaurants and freebies like WiFi in public areas and a theme park shuttle.

Pool

Hot Tub

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$139 total

Nov 18 - Nov 19

Total with taxes and fees

This smoke-free hotel features free water park access, 2 outdoor pools, and a restaurant. There's fun for all ages with a free kid's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 24-hour gym and perks like free WiFi.

Pool

Hot Tub

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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.

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 $744. 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.