Book Exclusive Winter Haven Vacation Packages

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Winter Haven flight + hotel packages

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

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Save 100% on your flight
Price was CA $1,259, price is now CA $841 per person
CA $841
per person
Nov 28 - Dec 5
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
Book a stay at this golf resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and 3 restaurants. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was CA $2,325, price is now CA $1,262 per person
CA $1,262
per person
Nov 28 - Dec 5
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
St Pete Beach Suites

St Pete Beach Suites

3 out of 5
Save 100% on your flight
Price was CA $2,262, price is now CA $1,407 per person
CA $1,407
per person
Nov 28 - Dec 5
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
Stay at this motel in St. Pete Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Upham Beach are located nearby.
Inn on the Beach - 18+ only

Inn on the Beach - 18+ only

2.5 out of 5
Pass-a-Grille
Save 100% on your flight
Price was CA $2,010, price is now CA $1,318 per person
CA $1,318
per person
Nov 28 - Dec 5
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
Book a stay at this beach motel in St. Pete Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Fort De Soto Park and Gulf Beaches Historical Museum are located nearby.
Provident Oceana Beachfront Suites

Provident Oceana Beachfront Suites

3.5 out of 5
Save 100% on your flight
Price was CA $2,017, price is now CA $1,336 per person
CA $1,336
per person
Nov 28 - Dec 5
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
Book a stay at this beach condo in Treasure Island. Enjoy 2 outdoor pools, a beach locale, and 2 hot tubs. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

Top Winter Haven hotels deals

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard Winter Haven FL
Free cancellation
The price is CA $156 per night
CA $156
CA $174 total
Oct 4 - Oct 5
includes taxes & fees
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LEGOLAND® Florida and Theatre Winter Haven are located nearby.
Pool
Parking included
Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

3.5 out of 5
5801 Roosevelt Dr Winter Haven FL
Free cancellation
Reserve now, pay when you stay
The price is CA $173 per night
CA $173
CA $194 total
Sep 30 - Oct 1
includes taxes & fees
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LEGOLAND® Florida and Peppa Pig Theme Park Florida are located nearby.
Pool
Breakfast included
Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

3 out of 5
305 5th St NW and Avenue D NW Winter Haven FL
Free cancellation
The price is CA $184 per night
CA $184
CA $206 total
Oct 4 - Oct 5
includes taxes & fees
Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LEGOLAND® Florida and Winter Haven Public Library are located nearby.
Pool
Breakfast included
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
The price is CA $278 per night
CA $278
CA $367 total
Sep 29 - Sep 30
includes taxes & fees
Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions LEGOLAND® Florida and Peppa Pig Theme Park Florida are located nearby.
Pool
Breakfast included
LEGOLAND Beach Retreat

LEGOLAND Beach Retreat

3 out of 5
100 Legoland Way SE Winter Haven FL
The price is CA $227 per night
CA $227
CA $310 total
Oct 12 - Oct 13
includes taxes & fees
Stay at this hotel in Winter Haven. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Popular attractions LEGOLAND® Florida and Peppa Pig Theme Park Florida are located nearby.
Pool
Breakfast included
Howard Johnson by Wyndham Winter Haven FL

Howard Johnson by Wyndham Winter Haven FL

2 out of 5
1300 3rd St Winter Haven FL
Free cancellation
Reserve now, pay when you stay
The price is CA $108 per night
CA $108
CA $121 total
Oct 1 - Oct 2
includes taxes & fees
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LEGOLAND® Florida and Indigo's Family Fun Center are located nearby.
Pool
Breakfast 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.

Stay near popular Winter Haven attractions

The entrance to LEGO Florida with colorful LEGO structures and a large LEGO sign.

LEGOLAND® Florida

9.0/10 (2,150 reviews)
Have a fun-filled day at LEGOLAND® Florida and find out why this is a popular theme park in Winter Haven. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
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Winter Haven Vacations

Sometimes getting lost is an excellent way to discover a new place. That being said, it's always good to brush up on some basic things about your destination before you head off. Read on for a few Winter Haven tips and tricks.

To help you get your bearings, Winter Haven sits 160 miles (257 kilometers) to the south of the notable city of Jacksonville.

There are approximately 34,000 locals that call this part of Lakeland - Winter Haven home.

Places to visit in Winter Haven

Got spare time up your sleeve? Stop by Legoland Florida, one of the area's most significant attractions.

Are you thirsty after a big day of sightseeing? Find a seat, raise your glass and relax with a drink at Indigo's Family Fun Center. Seeking some more ideas? The intimacy and accomplishment of theater has to be experienced. Buy your tickets for a play at Theatre Winter Haven and experience its charm and magic for yourself! But there's more. With its flickering lights and booming machines, Indigo's Billiards, Bowling & Games is a fun, stimulating place to spend a few hours. Have a whirl on pinball or just enjoy watching the young ones try and settle on which game to play first!

Where do you fly into for Winter Haven?

Coming in to land at Orlando International Airport (MCO)? After you've hopped off the plane and collected your belongings, downtown Winter Haven will be just 40 miles (64 kilometers) from 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 CA $841. 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 56 kilometers from Winter Haven.
Which airport is best for Winter Haven?
Many people choose to fly into Orlando Intl. Airport (MCO), 64 kilometers northeast of downtown Winter Haven. Others prefer Tampa Intl. Airport (TPA) (80 kilometers away from central Winter Haven) or Orlando Sanford Intl. Airport (SFB) (97 kilometers 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.

Photos of local treasures

Browse Winter Haven vacation photos for more inspiration

A castle entrance with flags and banners, including a LEGO Kingdoms banner.
A tree with hanging moss and sunlight filtering through the leaves.
A detailed LEGO model of a cityscape with prominent buildings like Luxor and a pyramid structure.
A pathway surrounded by large trees with extensive root systems.
A LEGO figure with a red face and a staff.