Lakeland - Winter Haven Vacation Packages 2025/2026 from $354

Lakeland - Winter Haven flight + hotel vacation packages

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

Mar Bay Motel &Suites

$354

per person

Oct 25 - Oct 28

found 1 hour ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A garden, a library, and a picnic area are also on offer.

Ocean Club Treasure Island Hotel

Save 100% on your flight

$737

per person

Nov 11 - Nov 17

found 20 hours ago

Roundtrip flight included

Denver (DEN) to Tampa (TPA)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

Clearwater Suites

Save 100% on your flight

$708

per person

Nov 11 - Nov 17

found 19 hours ago

Roundtrip flight included

Denver (DEN) to Tampa (TPA)

An outdoor pool is available at this hotel. Take advantage of the self parking.

The Avalon Club

Save 100% on your flight

$711

per person

Oct 24 - Oct 27

found 14 hours ago

Roundtrip flight included

Denver (DEN) 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.

Holiday Inn Express & Suites Trinity by IHG

Trinity

Save 100% on your flight

$377

per person

Dec 7 - Dec 12

found 2 hours ago

Roundtrip flight included

Chicago (ORD) to Tampa (TPA)

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

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

$189 nightly

$213 total

Oct 1 - Oct 2

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

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$149 total

Oct 9 - Oct 10

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

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$162 nightly

$184 total

Sep 28 - Sep 29

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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Free Cancellation

$148 nightly

$167 total

Sep 25 - Sep 26

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

voco Kissimmee Orlando by IHG

7888 W Irlo Bronson Hwy, Kissimmee, FL

Free Cancellation

$61 nightly

$69 total

Sep 30 - Oct 1

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

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd, Winter Garden, FL

Free Cancellation

Reserve now, pay when you stay

$138 nightly

$155 total

Oct 2 - Oct 3

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

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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

4.5/5(1,082 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.

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

4.5/5(64 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.

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

4.5/5(7 reviews)

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 $354. 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.