Book Exclusive Winter Haven Vacation Packages

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Winter Haven flight + hotel packages

Prices and availability subject to change. Additional terms may apply.
The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Jun. 3 - Jun. 7
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
Stay at this 4-star beach aparthotel in Clearwater Beach. Enjoy a beach locale, WiFi, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby. Discover genuine guest reviews for The Avalon Club along with the latest prices and availability – book now.
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Jun. 27 - Jul. 3
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
Stay at this 3-star beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the bar in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby. Discover genuine guest reviews for Thunderbird Beach Resort along with the latest prices and availability – book now.
Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
May 26 - Jun. 2
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
Stay at this 3-star beach hotel in St. Pete Beach. Enjoy free WiFi, a private beach, and room service. Our guests praise the pool and the bar in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby. Discover genuine guest reviews for Plaza Beach Hotel Beachfront Resort along with the latest prices and availability – book now.
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Belle Vista
Save 100% on your flight
per person
May 26 - Jun. 2
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
Stay at this 3-star family-friendly hotel in St. Pete Beach. Enjoy free WiFi, a marina, and room service. 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. Discover genuine guest reviews for Bay Palms Waterfront Resort - Hotel and Marina, in Belle Vista neighborhood, along with the latest prices and availability – book now.
Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Save 100% on your flight
per person
May 26 - Jun. 2
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
Stay at this 3-star family-friendly hotel in St. Pete Beach. Enjoy free WiFi, a marina, 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. Discover genuine guest reviews for Bayview Plaza Waterfront Resort, in Belle Vista neighborhood, along with the latest prices and availability – book now.

Top Winter Haven hotels deals

Holiday Inn Winter Haven, an IHG Hotel

Holiday Inn Winter Haven, an IHG Hotel

3 out of 5
200 Cypress Gardens Boulevard, Winter Haven, FL
Free cancellation
The price is CA $144 per night
CA $144
per night
May 2 - May 3
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. Discover genuine guest reviews for Holiday Inn Winter Haven, an IHG Hotel along with the latest prices and availability – book now.
Pool
Parking included
Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

2.5 out of 5
5801 Roosevelt Dr, Winter Haven, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $182 per night
CA $182
per night
May 1 - May 2
Stay at this business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LEGOLAND® Florida and Chain Of Wakes are located nearby. Discover genuine guest reviews for Best Western Plus Winter Haven Inn & Suites  along with the latest prices and availability – book now.
Pool
Breakfast included
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $130 per night
CA $130
per night
May 6 - May 7
Stay at this business-friendly motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions LEGOLAND® Florida and Indigo's Family Fun Center are located nearby. Discover genuine guest reviews for Howard Johnson by Wyndham Winter Haven FL along with the latest prices and availability – book now.
Pet-friendly
Pool
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $270 per night
CA $270
per night
May 8 - May 9
Stay at this 4-star family-friendly resort in Four Corners. Enjoy free WiFi, 3 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. Discover genuine guest reviews for The Grove Resort & Water Park Orlando along with the latest prices and availability – book now.
Hot tub
Pool
Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

3.5 out of 5
7600 Mystic Dunes Lane, Kissimmee, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $120 per night
CA $120
per night
May 1 - May 2
Stay at this 3.5-star golf hotel in Kissimmee. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions ESPN Wide World of Sports and Disney's Animal Kingdom® Theme Park are located nearby. Discover genuine guest reviews for Hilton Vacation Club Mystic Dunes Orlando along with the latest prices and availability – book now.
Pool
Breakfast available
Wyndham Orlando Resort & Conference Center, Celebration Area

Wyndham Orlando Resort & Conference Center, Celebration Area

3.5 out of 5
3011 Maingate Ln, Kissimmee, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $84 per night
CA $84
per night
Apr. 28 - Apr. 29
Stay at this 3.5-star family-friendly hotel in Kissimmee. Enjoy free parking, 2 outdoor pools, and breakfast. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby. Discover genuine guest reviews for Wyndham Orlando Resort & Conference Center, Celebration Area along with the latest prices and availability – book now.
Hot tub
Pet-friendly
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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

Image for LEGOLAND® Florida

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.

LEGOLAND® Florida
Image for Chain of Lakes Park

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.

Chain of Lakes Park
Image for Winter Haven Hospital

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 Hospital

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?
Your travel dreams can become reality in Winter Haven from just CA $1,170. Vacation packages include flights and hotels, so organizing everything should be a cinch. The only thing you’ll have to worry about is what amazing attraction you’ll head to first.
How long should my Winter Haven vacation be?
There’s no rule when it comes to how long you should spend in Winter Haven, but most travelers decide to stay for around 2 nights. Got some wiggle room in your departure date? Extend your vacation by a couple more nights. That way, you’ll have loads of time to explore the nearby areas as well.
Where can I get the best vacation package deals for Winter Haven?
Scoring the perfect package deal to Winter Haven is easy with Travelocity. With access to 400 air carriers and 665,000 properties across the globe, the choice is yours when it comes to your flights and hotels.
Why should I purchase my Winter Haven vacation package with Travelocity?
Incredible savings, countless enticing destinations and 24/7 customer service you can rely on — that’s why. And with our Price Match Guarantee, you can rest assured knowing that you’ll always score the best possible deal with Travelocity.
Can I save money on my Winter Haven car rental if I book it with a hotel or flight?
With a Winter Haven vacation package, you can bundle your car, flight and hotel bookings and save a whole lot. If you’re in the mood to uncover the best of this fantastic area, why not make a beeline for SeaWorld® Orlando? This well-known sight is 50 kilometersfrom Winter Haven. With your own set of wheels, you’ll be there in a jiffy.
What is the best time of year to go to Winter Haven?
are the months when most travelers visit, while are typically less busy. If you’re traveling with a limited budget, you’re better off visiting around . is generally regarded as the most expensive time of the year to come here.
Which airport is best for Winter Haven?
Orlando, FL (MCO-Orlando Intl.) is one of the most popular airports in Winter Haven. You’ll find it 60 kilometersnortheast of the downtown area. Other options open to you are Tampa, FL (TPA-Tampa Intl.) (80 kilometersaway from central Winter Haven) and Orlando, FL (SFB-Orlando Sanford Intl.) (95 kilometersaway from central Winter Haven).
What is there to do in Winter Haven?
While hopping off the tourist trail can be rewarding, you shouldn’t ignore the popular sights that make a place famous. Legoland Florida and Chain of Lakes Park are just two of them in Winter Haven.
Where should I stay when visiting Winter Haven?
Many tourists use Cypress Gardens as a starting point to discover the city of Winter Haven. Top hotels here include the Econo Lodge (3.0 stars) and the Holiday Inn Winter Haven (3.0 stars).
Can I go on vacation to Winter Haven at this time?
Don’t take off to Winter Haven without up-to-date facts about quarantine policies and travel restrictions. Travelocity’s Covid-19 Travel Advisor can fill you in. It has all the information you need to make your getaway as stress-free as possible.