Winter Haven Vacations 2025/2026 from CA $906

Winter Haven flight + hotel packages

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Innisbrook Resort

Save 100% on your flight

per person

Aug 23 - Aug 30

found 5 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Tampa (TPA)

Stay at this 3.5-star spa resort in Palm Harbor. Enjoy free WiFi, 6 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Innisbrook Golf Club and Leepa-Rattner Museum of Art are located nearby.

Ocean Club Treasure Island Hotel

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per person

Sep 2 - Sep 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this 4-star 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 St. Petersburg - Clearwater Beaches are located nearby.

FUSION Resort Waterfront Suites

Save 100% on your flight

per person

Sep 2 - Sep 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

Stay at this 3.5-star 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.

The Avalon Club

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per person

Aug 11 - Aug 17

found 22 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Tampa (TPA)

Stay at this 4-star 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.

The Hotel Zamora

Save 100% on your flight

per person

Aug 11 - Aug 17

found 22 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Tampa (TPA)

Stay at this 4-star beach hotel in St. Pete Beach. Enjoy a marina, 3 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.

Top Winter Haven hotels deals

Staybridge Suites Winter Haven Auburndale by IHG

305 5th St NW and Avenue D NW, Winter Haven, FL

Free cancellation

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Stay at this 3-star hotel in Winter Haven. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LEGOLAND® Florida and Winter Haven Public Library are located nearby.

Pool

Breakfast included

Best Western Plus Winter Haven Inn & Suites

5801 Roosevelt Dr, Winter Haven, FL

Free cancellation

Reserve now, pay when you stay

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Stay at this 3.5-star business-friendly hotel in Winter Haven. 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 Peppa Pig Theme Park Florida are located nearby.

Pool

Breakfast included

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Free cancellation

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Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.

Pool

Hot tub

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue, Winter Garden, FL

Free cancellation

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Stay at this 4-star family-friendly resort in Four Corners. Enjoy 6 outdoor pools, 3 restaurants, and 2 hot tubs. 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

Vacation Village at Parkway

2975 Arabian Nights Blvd, Kissimmee, FL

Free cancellation

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Stay at this 3-star family-friendly condo in Kissimmee. Enjoy free WiFi, 7 outdoor pools, and 7 hot tubs. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Old Town and ESPN Wide World of Sports Complex are located nearby.

Pool

Hot tub

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle, Kissimmee, FL

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Stay at this 4-star 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.

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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(72 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.

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.

Winter Haven Hospital

Though Winter Haven Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Winter Haven while you are here.

Winter Haven Vacations

Sometimes getting lost is an excellent way to discover a new place. That being said, it's always good to brush up on some basic things about your destination before you head off. Read on for a few Winter Haven tips and tricks.

To help you get your bearings, Winter Haven sits 160 miles (257 kilometers) to the south of the notable city of Jacksonville.

There are approximately 34,000 locals that call this part of Lakeland - Winter Haven home.

Places to visit in Winter Haven

Got spare time up your sleeve? Stop by Legoland Florida, one of the area's most significant attractions.

Are you thirsty after a big day of sightseeing? Find a seat, raise your glass and relax with a drink at Indigo's Family Fun Center. Seeking some more ideas? The intimacy and accomplishment of theater has to be experienced. Buy your tickets for a play at Theatre Winter Haven and experience its charm and magic for yourself! But there's more. With its flickering lights and booming machines, Indigo's Billiards, Bowling & Games is a fun, stimulating place to spend a few hours. Have a whirl on pinball or just enjoy watching the young ones try and settle on which game to play first!

Where do you fly into for Winter Haven?

Coming in to land at Orlando International Airport (MCO)? After you've hopped off the plane and collected your belongings, downtown Winter Haven will be just 40 miles (64 kilometers) from here.

Frequently asked questions

How much are vacation packages to Winter Haven?

Travelocity provides package deals to Winter Haven, including flights and hotels, starting from an impressive CA $906. With all the extra money, you could book some cool tours or even add a couple of extra days to your getaway.

How long should my Winter Haven vacation be?

Many travelers pack their suitcase and vacation in Winter Haven for about 2 nights. That's a great guide, but don't feel limited by it. Whether you only stay for a couple of days to see the famous attractions or settle in to uncover hidden gems, an unforgettable journey awaits.

Where can I get the best vacation package deals for Winter Haven?

Travelocity will be able to help you find an awesome Winter Haven package deal. With as many as 400 partner airlines and 1,000,000 properties across the world, there's no doubt you'll find the perfect mix.

Why should I book my Winter Haven vacation package with Travelocity?

With our Price Match Guarantee, we'll match any lower price you find. Add to that our 24/7 customer support and top-shelf service and your dream vacation is well within reach.

Will I save money on my Winter Haven car rental if I bundle it with a hotel or flight?

Certainly --- bundle your hotel, flight and car into a Winter Haven vacation package and you can save loads. With so much to see and do in the Winter Haven area, that rental vehicle will make exploring a joy. Once you've buckled up, get out on the wide open road and cruise toward Universal Studios Florida, a well-known sight roughly 56 kilometers from Winter Haven.

Which airport is best for Winter Haven?

Many people choose to fly into Orlando Intl. Airport (MCO), 64 kilometers northeast of downtown Winter Haven. Others prefer Tampa Intl. Airport (TPA) (80 kilometers away from central Winter Haven) or Orlando Sanford Intl. Airport (SFB) (97 kilometers away from central Winter Haven).

What is there to do in Winter Haven?

You'll notice a certain kind of magic as you stroll through the streets of Winter Haven. LEGOLAND® Florida and Chain of Lakes Park are just two famous sights that make this city so special, so put them on your itinerary.

Where should I stay when visiting Winter Haven?

Many people hit the hay at the Holiday Inn Winter Haven, an IHG Hotel. It's sure to be a good base for your Winter Haven vacation.