Lakeland - Winter Haven Vacation Packages 2025/2026 from $556

Lakeland - Winter Haven flight + hotel vacation packages

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

St Pete Beach Suites

Save 100% on your flight

$556

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Tampa (TPA)

This motel 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.

The Avalon Club

Save 100% on your flight

$992

per person

Nov 13 - Nov 19

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$777

per person

Dec 22 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Tampa (TPA)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 3 conference rooms, express check-out, and laundry service. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

ChartHouse Clearwater Beach Marina Hotel

Save 100% on your flight

$658

per person

Nov 13 - Nov 19

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) 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.

Christal Largo

Save 100% on your flight

$1,020

per person

Dec 21 - Dec 26

found 6 hours ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

An outdoor pool, free self parking, and laundry facilities are featured at this vacation home. WiFi in public areas is free. Barbecue grills and a virtual front desk are also provided.

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

$209 nightly

$235 total

Oct 6 - Oct 7

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

$171 nightly

$194 total

Oct 6 - Oct 7

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

$136 nightly

$155 total

Oct 12 - Oct 13

Total with taxes and fees

A golf course, 4 outdoor pools, and 2 outdoor tennis courts are all featured at this smoke-free property. 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 enjoy free perks like free self parking and WiFi in public areas.

Pool

Parking included

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Free Cancellation

$180 nightly

$203 total

Oct 7 - Oct 8

Total with taxes and fees

This traditional resort features a golf course, free water park access, and 8 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

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd, Winter Garden, FL

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$148 total

Oct 16 - Oct 17

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 mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Hot Tub

voco Kissimmee Orlando by IHG

7888 W Irlo Bronson Hwy, Kissimmee, FL

Free Cancellation

$60 nightly

$68 total

Oct 7 - Oct 8

Total with taxes and fees

This aparthotel features an outdoor pool and a gym. There's fun for all ages with a children's pool and a theme park shuttle, and families will appreciate the onsite laundry facilities. WiFi in public areas is free.

Pool

Free WiFi

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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.

Popular places to visit

LEGOLAND® Florida

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.

The 205 foot Neo-gothic 'singing tower' houses a 60-bell carillon – one of
about 185 carillons in North America.

Designed by Milton B. Medary, he was awarded in 1929 the American Institute of
Architects gold medal for this design.

#Trovember

Bok Tower Gardens

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.

This place is famous for its huge gators. I've been there several times and have always seen some. This guy, however, is an exceptionally large dude. I cut my hike short and let him sit in the sun.

The Circle B Bar Reserve

Explore the great outdoors at The Circle B Bar Reserve, a lovely green space in Lakeland. Check out the shops and top-notch restaurants in this family-friendly area.

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 $556. 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.