Winter Haven Vacation Packages

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Your Winter Haven Vacation

When a city getaway is calling, answer it with a Winter Haven vacation package. The neighborhood of Fussels Corner, which is great for golfing, nature and walking, makes a fantastic base for your adventures. You'll want to take in some sights during your trip to Winter Haven. Carve out some time for popular attractions like LEGOLAND® Florida, Chain of Lakes Park and Auburndale City Park. Don't put off visiting this destination any longer. The perfect Winter Haven vacation is just a few clicks away with Expedia.

Top Winter Haven Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (2,352 reviews)
Love the pool and the convenience of walking to the beach, shops, and dining.

Reviewed on Jul. 25, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
per person
Sep 13 - Sep 20
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,008 reviews)
Great choice..I will stay again for sure

Reviewed on Jul. 21, 2025

The Avalon Club

The Avalon Club

4 out of 5
per person
Aug 25 - Aug 29
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (430 reviews)
Great property and location

Reviewed on Jul. 21, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
per person
Aug 31 - Sep 6
found 11 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Tampa (TPA)
9.2/10 Wonderful! (1,040 reviews)
Wonderful reception

Reviewed on Jul. 14, 2025

Barsala At The Wayland Condos

Barsala At The Wayland Condos

4 out of 5
per person
Aug 28 - Sep 3
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
7.6/10 Good! (10 reviews)
My little getaway was amazing!!! The studio was beautiful, had everything we needed I wasn't expecting a full kitchen with baking utensils as well. We had a blast the view was incredible. I loved the outside setup near the pool as well. Will definitely be booking another getaway real soon!!

Reviewed on Jun. 10, 2025

Ready to book your vacation to Winter Haven?

 

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Winter Haven Hotel Deals

Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard, Winter Haven, FL
Fully refundable
The price is CA $127 per night from Aug 3 to Aug 4
CA $127
CA $143 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Only problem I had was with the curtains closing completely in the corner windows which left us slightly exposed. We worked around it so I still gave it 5 stars."

Reviewed on Jul. 22, 2025

Holiday Inn Winter Haven by IHG
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
Fully refundable
The price is CA $174 per night from Jul 28 to Jul 29
CA $174
CA $195 total
Jul 28 - Jul 29
includes taxes & fees
9.6/10 Exceptional! (449 reviews)
"We had a real good stay we enjoyed very much the staff were very helpful, with our stay ."

Reviewed on Jul. 22, 2025

Staybridge Suites Winter Haven Auburndale by IHG
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
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Jul 28 to Jul 29
CA $179
CA $201 total
Jul 28 - Jul 29
includes taxes & fees
9.4/10 Exceptional! (903 reviews)
"Excellent!"

Reviewed on Jul. 22, 2025

Best Western Plus Winter Haven Inn & Suites 
See all 38,486 properties in Winter Haven
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Winter Haven

Legoland Florida featuring a pond, a garden and a river or creek

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.

LEGOLAND® Florida

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

Northgate Shopping Center

You can search for that perfect souvenir at Northgate Shopping Center during your stay in Cypress Gardens. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Northgate Shopping Center

What to do in Winter Haven

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $108
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Winter Haven

Frequently asked questions

How much does a Winter Haven vacation package cost?
You'll find cheap prices from CA $749 on Expedia for your Winter Haven escape. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Winter Haven costs.
What are the cheapest months to go to Winter Haven?
You can typically find lower rates and greater availability in September, October and November. Check out our cheap Winter Haven vacation packages and you could get some great off-season discounts.
How many days is enough for Winter Haven?
Dedicate around 2 days for your Winter Haven vacation to really discover all that makes this place special. Explore popular areas, including Cypress Gardens and Jan Phyl Village. Then make a beeline for top attractions like Auburndale City Park and Theatre Winter Haven. With a good itinerary, you'll be kept busy with room for some downtime too. Want to venture outside of Winter Haven? Consider fitting in an excursion or two.
Is it worth booking a vacation package to Winter Haven?
Whether you're looking to visit top attractions like Chain of Lakes Park and Theatre Winter Haven on your Winter Haven vacation, or coming for its great fishing, walking trails and golfing, there's something for everyone here. With so much to do, you'll soon find out why so many visitors think Winter Haven is a good vacation destination.
How to find the best Winter Haven package deals?
Start your search for a Winter Haven package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Winter Haven package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Winter Haven adventure off to a flying start.
Is it cheaper to book a Winter Haven vacation as a package?
You can enjoy significant savings on your next Winter Haven break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winter Haven?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Winter Haven getaway.
How to plan a trip to Winter Haven?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Winter Haven.
  2. Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and flights. Your accommodations will probably be the largest expense during your trip to Winter Haven.
  3. Set the duration of your trip: Start by listing all the attractions and activities you want to experience in Winter Haven. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Winter Haven vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.