Winter Haven Vacation Packages 2025/2026 from $432

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

per person

Sep 21 - Sep 26

found 14 hours ago

Roundtrip flight included

Dallas (DFW) 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.

Mar Bay Motel &Suites

Save 100% on your flight

per person

Jul 28 - Aug 3

found 19 hours ago

Roundtrip flight included

Dallas (DFW) 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.

Ocean Club Treasure Island Hotel

Save 100% on your flight

per person

Sep 8 - Sep 12

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

This hotel features an outdoor pool and a hot 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.

Barsala At The Wayland Condos

Save 100% on your flight

per person

Aug 29 - Sep 1

found 1 day ago

Roundtrip flight included

Indianapolis (IND) to Tampa (TPA)

This aparthotel features an outdoor pool and a gym. WiFi in public areas is free. Barbecue grills and a virtual front desk are also provided.

The Avalon Club

Save 100% on your flight

per person

Aug 2 - Aug 6

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Top Winter Haven hotels deals

Staybridge Suites Winter Haven Auburndale by IHG

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

Free Cancellation

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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

Best Western Plus Winter Haven Inn & Suites

5801 Roosevelt Dr, Winter Haven, FL

Free Cancellation

Reserve now, pay when you stay

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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

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue, Winter Garden, FL

Free Cancellation

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Free water park access, 3 restaurants, and 6 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 3 poolside bars and enjoy the 2 hot tubs and 24-hour gym.

Pool

Hot Tub

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Free Cancellation

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2 hot tubs, an outdoor pool, and a 24-hour gym are all featured at this smoke-free resort. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

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This smoke-free resort features free water park access, a full-service spa, and 3 restaurants. Bring the family and enjoy the lazy river, waterslide, and arcade/game room. Enjoy the 3 outdoor pools and perks like free WiFi.

Pool

Hot Tub

Delta Hotels by Marriott Orlando Celebration

2900 Parkway Blvd, Kissimmee, FL

Free Cancellation

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This smoke-free hotel features 4 restaurants, 2 outdoor pools, and 2 outdoor tennis courts. Traveling on business? Take advantage of the 9 conference rooms, free WiFi in public areas, and express check-in. Unwind with drinks at one of the 2 bars/lounges or the poolside bar and make the most of the 2 hot tubs.

Pool

Hot Tub

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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)

You can take time to visit Chain of Lakes Park during your travels to Winter Haven. Amble around this family-friendly area's lakeside and enjoy 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 $432. 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.