Lakeland - Winter Haven Vacations 2026 from CA $882

Lakeland - Winter Haven flight + hotel packages

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

Holiday Inn Express Lake Wales N-Winter Haven by IHG

CA $882

per person

Feb 17 - Feb 24

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this business-friendly hotel in Lake Wales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LEGOLAND® Florida and Eagle Ridge Mall are located nearby.

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Town 'n' Country

CA $927

per person

Mar 24 - Mar 29

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Tampa (TPA)

Book a stay at this spa villa in Tampa. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Raymond James Stadium and George M. Steinbrenner Field are located nearby.

FUSION Resort Waterfront Suites

CA $1,835

per person

Mar 15 - Mar 20

found 21 hours ago

Roundtrip flight included

Halifax (YHZ) to Tampa (TPA)

Stay at this aparthotel in Treasure Island. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

Plaza Beach Hotel Beachfront Resort

CA $1,944

per person

Mar 17 - Mar 22

found 18 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a private beach, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.

Bayview Plaza Waterfront Resort

Belle Vista

CA $1,615

per person

Mar 14 - Mar 21

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.

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

CA $228

CA $333 total

Jan 12 - Jan 13

includes taxes & fees

Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Margaritaville Resort Orlando

8000 Fins Up Circle Kissimmee FL

Free cancellation

Reserve now, pay when you stay

CA $194

CA $295 total

Jan 12 - Jan 13

includes taxes & fees

Book a stay at this spa resort in Kissimmee. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

Free cancellation

Reserve now, pay when you stay

CA $139

CA $205 total

Jan 19 - Jan 20

includes taxes & fees

Book a stay at this golf property in Kissimmee. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the pool and the restaurant in our reviews. Popular attractions ESPN Wide World of Sports Complex and Disney's Animal Kingdom® Theme Park are located nearby.

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL

Free cancellation

CA $150

CA $229 total

Jan 11 - Jan 12

includes taxes & fees

Book a stay at this golf resort in Kissimmee. Enjoy free WiFi, free parking, and 7 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Destiny Palms Hotel Maingate West

8536 W Irlo Bronson Memorial Hwy Kissimmee FL

Free cancellation

Reserve now, pay when you stay

CA $95

CA $114 total

Feb 2 - Feb 3

includes taxes & fees

Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd Winter Garden FL

Free cancellation

Reserve now, pay when you stay

CA $147

CA $205 total

Jan 22 - Jan 23

includes taxes & fees

Book a stay at this family-friendly hotel in Four Corners. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

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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

Have a fun-filled day at LEGOLAND® Florida and find out why this is a popular theme park in Winter Haven. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

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.

Dinosaur World

You can spend time exploring the galleries in Dinosaur World in Plant City. Wander around the area's picturesque gardens or experience its lively festivals.

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 CA $882. 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.