Lakeland - Winter Haven Vacations 2026 from CA $1,460

Lakeland - Winter Haven flight + hotel packages

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

CW Hotel

CA $1,460

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this hotel in Clearwater Beach. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

Cedar Cove Resort and Cottages

CA $1,836

per person

Aug 1 - Aug 8

found 18 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Tampa (TPA)

Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Coquina Beach and Bean Point Beach are located nearby.

The Avalon Club

CA $1,738

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Book a stay at this beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $2,104

per person

Aug 1 - Aug 8

found 18 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Tampa (TPA)

Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Pass-a-Grille Beach are located nearby.

Driftwood at Anna Maria Island Inn

CA $1,849

per person

Aug 1 - Aug 8

found 18 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Tampa (TPA)

Stay at this motel in Holmes Beach. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Anna Maria Beach and Bean Point Beach 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 $233

CA $338 total

Jun 8 - Jun 9

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.

Pool

Hot tub

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

Free cancellation

Reserve now, pay when you stay

CA $197

CA $298 total

Jun 3 - Jun 4

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.

Pool

Hot tub

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL

Free cancellation

CA $206

CA $285 total

Jun 1 - Jun 2

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.

Pool

Hot tub

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

Free cancellation

Reserve now, pay when you stay

CA $138

CA $204 total

Jun 7 - Jun 8

includes taxes & fees

Book a stay at this golf hotel in Kissimmee. Enjoy free WiFi, 4 outdoor pools, and a golf course. 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.

Pool

Free WiFi

Omni Orlando Resort at ChampionsGate

1500 Masters Blvd Davenport FL

Free cancellation

Reserve now, pay when you stay

CA $242

CA $353 total

Jun 7 - Jun 8

includes taxes & fees

Book a stay at this spa hotel in Four Corners. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions ChampionsGate Golf Club and Reunion Resort Golf Course are located nearby.

Pool

Hot tub

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL

Free cancellation

CA $157

CA $176 total

Jun 14 - Jun 15

includes taxes & fees

Book a stay at this business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LEGOLAND® Florida and Theatre Winter Haven are located nearby.

Pool

Parking included

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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(73 reviews)

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.

Wooton park on lake Dora in Tavares, Florida

Lakeside Village

You can search for that perfect souvenir at Lakeside Village during your visit to Lakeland. Amble around the area's lakeside or attend a sporting event.

Scenic view of Winter Park, Chain of Lakes canal. The Chain of Lakes is a popular tourist destination for residents and visitors to Winter Park, Florida, USA.

Chain of Lakes Park

3/5(1 review)

Catch an event at Chain of Lakes Park during your trip to Winter Haven. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

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 $1,460. 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.