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.
Holiday Inn Express St. Petersburg North (I-275) by IHG

Holiday Inn Express St. Petersburg North (I-275) by IHG

2.5 out of 5
Lealman
Price was CA $1,350, price is now CA $882 per person
CA $882
per person
Apr 10 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
Book a stay at this business-friendly hotel in St. Petersburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vinoy Park and Salvador Dali Museum are located nearby.
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Palm River-Clair Mel
Price was CA $1,605, price is now CA $948 per person
CA $948
per person
Mar 15 - Mar 21
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this spa vacation home in Tampa. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Seminole Hard Rock Casino Tampa and Port of Tampa are located nearby.
FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $3,084, price is now CA $1,831 per person
CA $1,831
per person
Apr 10 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
Stay at this aparthotel in Treasure Island. Enjoy free WiFi, free parking, and a rooftop terrace. 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.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,442, price is now CA $925 per person
CA $925
per person
Apr 20 - Apr 25
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Tampa (TPA)
Stay at this hotel in Safety Harbor. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Philippe Park and Chi Chi Rodriguez Golf Club are located nearby.
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Price was CA $1,580, price is now CA $1,036 per person
CA $1,036
per person
Apr 6 - Apr 11
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy 2 bars/lounges, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Tampa Riverwalk and Port of Tampa are located nearby.

Top Winter Haven hotels deals

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 $126 per night
CA $126
CA $141 total
Feb 17 - Feb 18
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
Legoland Florida Hotel

Legoland Florida Hotel

3 out of 5
1 Legoland Way Winter Haven FL
The price is CA $358 per night
CA $358
CA $454 total
Mar 1 - Mar 2
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 $268 per night
CA $268
CA $353 total
Feb 6 - Feb 7
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
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Free cancellation
Reserve now, pay when you stay
The price is CA $216 per night
CA $216
CA $319 total
Feb 2 - Feb 3
includes taxes & fees
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Pool
Hot tub
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Free cancellation
Reserve now, pay when you stay
The price is CA $154 per night
CA $154
CA $228 total
Feb 2 - Feb 3
includes taxes & fees
Stay at this resort in Kissimmee. Enjoy free WiFi, 2 hot tubs, and 2 outdoor pickleball courts. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Pool
Hot tub
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4 out of 5
8505 W Irlo Bronson Memorial Hwy Kissimmee FL
Free cancellation
The price is CA $188 per night
CA $188
CA $271 total
Feb 1 - Feb 2
includes taxes & fees
Book a stay at this golf resort in Kissimmee. Enjoy free WiFi, free parking, and 7 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
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 featuring signage, a garden and rides

LEGOLAND® Florida

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.

LEGOLAND® Florida
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

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.

Chain of Lakes Park
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.

Rotary Park

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 $882. 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

Winter Haven
Winter Haven
Legoland Florida which includes signage and rides
Winter Haven which includes a park
Legoland Florida which includes rides, a statue or sculpture and outdoor art