Winter Haven Vacation Packages 2026 from $753

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

$753

per person

Apr 23 - Apr 30

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.

Island Grand at TradeWinds

$1,241

per person

Apr 25 - May 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A water park, 4 restaurants, and 5 outdoor pools are all featured at this resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the children's club, mini golf, and children's pool.

Plaza Beach Hotel Beachfront Resort

Save 100% on your flight

$1,023

per person

Apr 30 - May 5

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.

The Sarasota Modern, a Tribute Portfolio Hotel

Central Sarasota

Save 100% on your flight

$970

per person

Apr 17 - Apr 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This smoke-free hotel features 3 outdoor pools, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A poolside bar, a 24-hour front desk, and a terrace are also provided.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$1,005

per person

Apr 13 - Apr 19

found 1 day ago

Roundtrip non-stop 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.

Top Winter Haven hotels deals

Howard Johnson by Wyndham Winter Haven FL

1300 3rd St Winter Haven FL

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$114 total

Feb 23 - Feb 24

Total with taxes and fees

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.

LEGOLAND Beach Retreat

100 Legoland Way SE Winter Haven FL

$289 nightly

$324 total

Feb 27 - Feb 28

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Relax with a drink at the poolside bar and enjoy the free full breakfast each morning. Self parking and a safe deposit box are also offered on site.

Pool

Breakfast included

Legoland Florida Hotel

1 Legoland Way Winter Haven FL

$298 nightly

$333 total

Mar 3 - Mar 4

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

$208 nightly

$234 total

Feb 22 - Feb 23

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.

Vacation Village Orlando, Celebration

2975 Arabian Nights Blvd Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$122 total

Mar 10 - Mar 11

Total with 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

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$104 total

Mar 1 - Mar 2

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

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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.

Scenic view of Winter Park, Chain of Lakes canal. The Chain of Lakes is a popular tourist destination for residents and visitors to Winter Park, Florida, USA.

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.

Sunrise at Rotary Riverfront Park, Titusville, Florida

Rotary Park

Rotary Park is just one of the places to see in Winter Haven, so why not enjoy the other things to explore during your travels? 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 $753. 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.