Winter Haven Vacation Packages 2026 from $715

Winter Haven flight + hotel vacation packages

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

ChartHouse Clearwater Beach Marina Hotel

Save 100% on your flight

$715

per person

Sep 23 - Sep 30

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.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$921

per person

Oct 7 - Oct 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$946

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.

The Avalon Club

Save 100% on your flight

$1,621

per person

Oct 31 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

CW Hotel

Save 100% on your flight

$871

per person

Sep 19 - Sep 26

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.

Top Winter Haven hotels deals

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$100 total

Aug 30 - Aug 31

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.

Best Western Plus Winter Haven Inn & Suites

5801 Roosevelt Dr Winter Haven FL

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$128 total

Aug 23 - Aug 24

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.

Staybridge Suites Winter Haven Auburndale by IHG

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

Free Cancellation

$103 nightly

$115 total

Aug 30 - Aug 31

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.

LEGOLAND Beach Retreat

100 Legoland Way SE Winter Haven FL

$198 nightly

$222 total

Sep 12 - Sep 13

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.

Legoland Florida Hotel

1 Legoland Way Winter Haven FL

$269 nightly

$301 total

Aug 23 - Aug 24

Total with taxes and fees

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.

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

Aug 22 - Aug 23

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.

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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.

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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 $715. 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.