Winter Haven Vacation Packages 2026 from $505

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

$505

per person

Jul 24 - Jul 28

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Cedar Cove Resort and Cottages

Save 100% on your flight

$608

per person

Jul 30 - Aug 2

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Tampa (TPA)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.

BeachTrail Lodging

Save 100% on your flight

$842

per person

Jul 22 - Jul 29

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Tampa (TPA)

This condo 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 food and water bowls. A terrace and laundry facilities are also provided.

Surf Beach Treasure Island Resort

Save 100% on your flight

$1,282

per person

Jul 22 - Jul 29

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Tampa (TPA)

This aparthotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a picnic area, and laundry facilities are also on offer.

Wyndham Grand Clearwater Beach

Save 100% on your flight

$785

per person

Jul 24 - Jul 28

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Tampa (TPA)

A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, express check-out, and valet parking. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.

Top Winter Haven hotels deals

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL

Free Cancellation

$114 nightly

$128 total

May 31 - Jun 1

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

$130 nightly

$146 total

May 31 - Jun 1

Total with taxes and fees

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like full breakfast and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

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

May 24 - May 25

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

$127 nightly

$142 total

Jun 14 - Jun 15

Total with taxes and fees

An outdoor pool is featured at this hotel, along with free WiFi in public areas and a fireplace in the lobby. Enjoy the free continental breakfast each morning. A computer station, luggage storage, and laundry facilities are also on offer.

Pool

Breakfast included

Legoland Florida Hotel

1 Legoland Way Winter Haven FL

$340 nightly

$381 total

May 21 - May 22

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.

Pool

Breakfast included

LEGOLAND Beach Retreat

100 Legoland Way SE Winter Haven FL

$214 nightly

$240 total

May 31 - Jun 1

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

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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(1,095 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.

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

4/5(84 reviews)

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.

Sunrise at Rotary Riverfront Park, Titusville, Florida

Rotary Park

Rotary Park is just one of the places to see in Winter Haven, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

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 $505. 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.