Winter Haven Vacation Packages 2026 from $406

Winter Haven flight + hotel vacation packages

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

Mar Bay Motel &Suites

Save 100% on your flight

$406

per person

Aug 11 - Aug 16

found 10 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.

ChartHouse Clearwater Beach Marina Hotel

$656

per person

Sep 19 - Sep 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. A rooftop terrace is on site, and self parking and a 24-hour front desk are also offered.

CW Hotel

$992

per person

Sep 19 - Sep 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and concierge services.

St Pete Beach Suites

Save 100% on your flight

$568

per person

Aug 7 - Aug 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.

Legoland Florida Hotel

Save 100% on your flight

$576

per person

Aug 22 - Aug 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This smoke-free hotel features a water park, 2 outdoor pools, and a restaurant. Unwind with a drink at the bar/lounge and enjoy perks like free full breakfast and free WiFi. Valet parking, express check-in, and luggage storage are also offered.

Top Winter Haven hotels deals

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL

Free Cancellation

$106 nightly

$119 total

Aug 2 - Aug 3

Total with taxes and fees

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Parking included

Best Western Plus Winter Haven Inn & Suites

5801 Roosevelt Dr Winter Haven FL

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$134 total

Jul 5 - Jul 6

Total with taxes and fees

This hotel features an outdoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Pool

Breakfast included

Legoland Florida Hotel

1 Legoland Way Winter Haven FL

$298 nightly

$333 total

Jul 5 - Jul 6

Total with taxes and fees

Pool

Breakfast included

LEGOLAND Beach Retreat

100 Legoland Way SE Winter Haven FL

$170 nightly

$191 total

Aug 2 - Aug 3

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Relax with a drink at the poolside bar and enjoy the free full breakfast each morning. Self parking and a safe deposit box are also offered on site.

Pool

Breakfast included

Howard Johnson by Wyndham Winter Haven FL

1300 3rd St Winter Haven FL

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$95 total

Jul 7 - Jul 8

Total with taxes and fees

This motel features a restaurant, an outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Pool

Breakfast included

Staybridge Suites Winter Haven Auburndale by IHG

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

Free Cancellation

$121 nightly

$136 total

Jul 26 - Jul 27

Total with taxes and fees

This hotel features an outdoor pool and a gym. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A lobby fireplace, a computer station, and luggage storage are also on offer.

Pool

Breakfast 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.

Stay near popular Winter Haven attractions

A detailed model of a cityscape with various buildings, including a tall skyscraper, a modern building, and a historic building with a red roof.

LEGOLAND® Florida

9.0/10 (2,150 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.

See properties

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 $406. 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 35 mi from Winter Haven.

Which airport is best for Winter Haven?

Many people choose to fly into Orlando Intl. Airport (MCO), 40 mi northeast of downtown Winter Haven. Others prefer Tampa Intl. Airport (TPA) (50 mi away from central Winter Haven) or Orlando Sanford Intl. Airport (SFB) (60 mi 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.