Winter Haven Vacation Packages 2025/2026 from $553

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

$553

per person

Jan 26 - Feb 2

found 1 day ago

Roundtrip flight included

Boston (BOS) 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. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

The Avalon Club

$975

per person

Jan 17 - Jan 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,152

per person

Jan 26 - Feb 2

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$1,226

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 3 conference rooms, express check-out, and laundry service. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Plaza Beach Hotel Beachfront Resort

Save 100% on your flight

$674

per person

Jan 26 - Feb 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A private beach and an outdoor pool are featured at this hotel. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site.

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

$135 nightly

$151 total

Nov 16 - Nov 17

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

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

Nov 16 - Nov 17

Total with 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

Legoland Florida Hotel

1 Legoland Way, Winter Haven, FL

$303 nightly

$340 total

Dec 2 - Dec 3

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

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue, Winter Garden, FL

Free Cancellation

Reserve now, pay when you stay

$205 nightly

$231 total

Dec 1 - Dec 2

Total with 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. Enjoy the 2 hot tubs and perks like free WiFi.

Pool

Hot Tub

Holiday Inn Resort Kissimmee by the Parks by IHG

3011 Maingate Ln, Kissimmee, FL

Free Cancellation

$76 nightly

$86 total

Nov 30 - Dec 1

Total with taxes and fees

2 outdoor pools, a 24-hour gym, and a hot tub are all featured at this smoke-free hotel. Bring the family and enjoy the children's pool, playground, and kid-friendly dining. Enjoy a meal from the a restaurant and perks like free self parking.

Pool

Hot Tub

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$145 total

Nov 17 - Nov 18

Total with taxes and fees

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.

Pool

Parking 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(1,082 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 $553. 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.