Winter Haven Vacations from $368
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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.
The Latest Winter Haven vacation packages
Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
Save 100% on your flight
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (499 reviews)
We enjoyed the immaculate unit which offered all the amenities that we could possibly ask for. It was tastefully decorated with comfortable furnishings. All the personnel we spoke with were friendly and eager to help with any questions we had. A very enjoyable stay!!
Reviewed on Jun 29, 2025
Barsala At The Wayland Condos
Save 100% on your flight
per person
Aug 3 - Aug 10
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
7.8/10 Good! (9 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
Hibiscus Suites - Gateway to Siesta Key
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
8.6/10 Excellent! (2,137 reviews)
Adorable property!! A block away from the bridge to cross over to Siesta Key beach. 7-Eleven 4 minutes away to get ice, beach necessities. Didn't use the pool, but there is parking in front of the rooms. The room itself very comfortable, full kitchen you can cook and it has all items needed to make and serve a meal, full size fridge, good hvac unit to cool the room. Sleeper couch in living room and queen size bed. Super cozy, cute and very comfortable. Would love to return next time we are visiting Siesta Key.
Reviewed on Jun 23, 2025
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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.
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.
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.
What to do in Winter Haven
Winter Haven Hotel Deals
Staybridge Suites Winter Haven Auburndale by IHG
305 5th St NW and Avenue D NW, Winter Haven, FL
Fully refundable
$135 nightly
The price is $151 total per night from Jul 6 to Jul 7
$151 total
Jul 6 - Jul 7
Total includes taxes and fees
9.6/10 Exceptional! (393 reviews)
"Good property and quality service"
Reviewed on Jun 26, 2025
Best Western Plus Winter Haven Inn & Suites
5801 Roosevelt Dr, Winter Haven, FL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $134 total per night from Jul 1 to Jul 2
$134 total
Jul 1 - Jul 2
Total includes taxes and fees
9.4/10 Exceptional! (863 reviews)
"This is the Best Best Western we've stayed at. It is brand new so eveything is fresh. Good value."
Reviewed on Jun 30, 2025
Kompose Boutique Resort at Theme Parks
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $111 total per night from Jul 1 to Jul 2
$111 total
Jul 1 - Jul 2
Total includes taxes and fees
9.6/10 Exceptional! (424 reviews)
"First time staying here.. staff was super friendly. 10/10 recommend"
Reviewed on Jun 28, 2025
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.
Find the Best Winter Haven Vacation Packages
Winter Haven Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 33,900 |
Max Temp Winter | 70ºF |
Max Temp Summer | 90ºF |
Top Sights | LEGOLAND® Florida, Theatre Winter Haven and True Blue Winery |
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- Hotels near Indigo's Family Fun Center
- Hotels near Indigo's Billiards
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.