Winter Haven Vacation Packages 2024/2025 from $328

Winter Haven flight + hotel vacation packages

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

Highland Down Town Tampa

Old Seminole Heights

Save 100% on your flight

per person

Jan 15 - Jan 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This vacation home features a garden, laundry facilities, and free self parking. A virtual front desk are provided for your convenience.

Ocean Club Treasure Island Hotel

per person

Feb 8 - Feb 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a spa tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

The Hotel Zamora

Save 100% on your flight

per person

Dec 31 - Jan 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 3 conference rooms, along with the 24-hour business center. Make the most of the outdoor pool and gym, and relax with drinks at one of the 3 bars/lounges.

The Saint Hotel

Save 100% on your flight

per person

Dec 31 - Jan 6

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 spa tub and perks like free self parking and free WiFi. A terrace, express check-in, and express check-out are also on offer.

Legacy Vacation Resorts - Indian Shores

Save 100% on your flight

per person

Dec 31 - Jan 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features an outdoor pool and a gym. Enjoy the spa tub and perks like free self parking and free WiFi. A business center, a terrace, and laundry facilities are also on offer.

Top Winter Haven hotels deals

Best Western Plus Winter Haven Inn & Suites

5801 Roosevelt Dr, Winter Haven, FL

Free Cancellation

Reserve now, pay when you stay

$139

includes taxes & fees

$124 per night

Dec 1 - Dec 2

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.

Holiday Inn Winter Haven, an IHG Hotel

200 Cypress Gardens Boulevard, Winter Haven, FL

Free Cancellation

$111

includes taxes & fees

$99 per night

Dec 1 - Dec 2

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.

Howard Johnson by Wyndham Winter Haven FL

1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL

Free Cancellation

Reserve now, pay when you stay

$114

includes taxes & fees

$102 per night

Nov 24 - Nov 25

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.

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue, Winter Garden, FL

Free Cancellation

Reserve now, pay when you stay

$193

includes taxes & fees

$177 per night

Dec 12 - Dec 13

Free water park access, 3 restaurants, and 3 outdoor pools are all featured at this resort. Bring the family and enjoy the lazy river, children's club, and mini golf. Relax with a drink at one of the 2 poolside bars and get perks like free WiFi.

Seralago Hotel & Suites Main Gate East

5678 West Irlo Bronson Memorial Hwy, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$65

includes taxes & fees

$57 per night

Nov 24 - Nov 25

2 outdoor pools, an outdoor tennis court, and a spa tub are all featured at this aparthotel. Bring the family and enjoy the children's pool, free theme park shuttle, and playground. Enjoy the gym and perks like free self parking and free WiFi.

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$125

includes taxes & fees

$110 per night

Dec 15 - Dec 16

A golf course, 4 outdoor pools, and 2 outdoor tennis courts are all featured at this smoke-free property. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

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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(1,082 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.

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.

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.

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 $328. 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.