Winter Haven Vacation Packages 2026 from $413

Winter Haven flight + hotel vacation packages

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

Saddlebrook Resort

Wesley Chapel South

Save 100% on your flight

$413

per person

Mar 18 - Mar 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This resort features a golf course, a full-service spa, and 3 restaurants. Bring the family and enjoy the children's pool, playground, and kid-friendly dining. Enjoy the 2 outdoor pools and perks like free WiFi.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,416

per person

Mar 14 - Mar 21

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.

Mar Bay Motel &Suites

Save 100% on your flight

$500

per person

Feb 18 - Feb 24

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

FUSION Resort Waterfront Suites

Save 100% on your flight

$1,439

per person

Mar 21 - Mar 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and perks like free self parking and free WiFi. A 24-hour business center, luggage storage, and concierge services are also on offer.

Plaza Beach Hotel Beachfront Resort

Save 100% on your flight

$1,364

per person

Mar 19 - Mar 24

found 24 hours ago

Roundtrip non-stop 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

Best Western Plus Winter Haven Inn & Suites

5801 Roosevelt Dr Winter Haven FL

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$164 total

Jan 14 - Jan 15

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

Legoland Florida Hotel

1 Legoland Way Winter Haven FL

$302 nightly

$339 total

Jan 22 - Jan 23

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

$218 nightly

$245 total

Jan 13 - Jan 14

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

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$68 nightly

$77 total

Jan 13 - Jan 14

Total with taxes and fees

2 hot tubs, an outdoor pool, and a 24-hour gym are all featured at this smoke-free resort. Enjoy the sauna and free perks like buffet breakfast and WiFi in public areas. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.

Pool

Hot Tub

Margaritaville Resort Orlando

8000 Fins Up Circle Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$195 nightly

$222 total

Jan 19 - Jan 20

Total with taxes and fees

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

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$148 total

Jan 20 - Jan 21

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

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

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.

Theatre Winter Haven

You can enjoy a show at Theatre Winter Haven during your trip to Winter Haven. 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 $413. 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.