Winter Haven Vacation Packages 2025 from $344

Winter Haven flight + hotel vacation packages

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

Kompose Boutique Hotel

Save 100% on your flight

per person

Aug 9 - Aug 14

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Tampa (TPA)

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Mar Bay Motel &Suites

per person

Jul 13 - Jul 19

found 16 hours ago

Roundtrip flight included

Detroit (DTW) 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

Jul 11 - Jul 15

found 24 hours ago

Roundtrip flight included

Hartford (BDL) 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.

The Avalon Club

Save 100% on your flight

per person

Jul 7 - Jul 11

found 1 day ago

Roundtrip flight included

Hartford (BDL) 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.

Siesta Key Palms Resort

Save 100% on your flight

per person

Aug 16 - Aug 19

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Tampa (TPA)

This hotel features 2 outdoor pools and a bar/lounge. A terrace, a garden, and a picnic area 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

$119 nightly

$134 total

Jun 9 - Jun 10

Total includes 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

Staybridge Suites Winter Haven Auburndale by IHG

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

Free Cancellation

$134 nightly

$150 total

Jun 8 - Jun 9

Total includes 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

Home2 Suites By Hilton Winter Haven

6015 Cypress Gardens Blvd, Winter Haven, FL

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$142 total

Jun 15 - Jun 16

Total includes taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue, Winter Garden, FL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$190 total

Jun 8 - Jun 9

Total includes taxes and fees

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

Reserve now, pay when you stay

$91 nightly

$104 total

Jun 5 - Jun 6

Total includes taxes and fees

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

Vacation Village at Parkway

2975 Arabian Nights Blvd, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$113 nightly

$128 total

Jun 5 - Jun 6

Total includes taxes and fees

7 outdoor pools, 7 hot tubs, and a gym are all featured at this smoke-free condo. Bring the family and enjoy the children's pool, playground, and arcade/game room. WiFi in public areas is free.

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 $344. 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.