Winter Haven Vacations from $550
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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.
The Westin Sarasota
Central Sarasota
Save 100% on your flight
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,057 reviews)
Easy to navigate and hotel takes you to Lido beach where you can rent chairs/umbrellas and have access to food. You can Uber to Siesta beach and order drinks and food from your chair at the beach. I love that!
Reviewed on Aug 4, 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
$127 nightly
The price is $142 total per night from Aug 12 to Aug 13
$142 total
Aug 12 - Aug 13
Total includes taxes and fees
9.6/10 Exceptional! (485 reviews)
"Spacious rooms"
Reviewed on Aug 8, 2025
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard, Winter Haven, FL
Fully refundable
$93 nightly
The price is $104 total per night from Aug 17 to Aug 18
$104 total
Aug 17 - Aug 18
Total includes taxes and fees
8.8/10 Excellent! (1,000 reviews)
Excellent hotel
"This holiday Inn property was wonderful. Checkin was simple ,easy and I was given free food vouchers for my daughter for breakfast and dinner (with 1 adult paying adult. The breakfast was a full breakfast with all variety of items;Well worth it. Our room was clean and very spacious (1king bed & daybed ..."
Reviewed on Aug 6, 2025
Best Western Plus Winter Haven Inn & Suites
5801 Roosevelt Dr, Winter Haven, FL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $142 total per night from Aug 12 to Aug 13
$142 total
Aug 12 - Aug 13
Total includes taxes and fees
9.4/10 Exceptional! (937 reviews)
"Great location. Great staff.. Clean, modern spacious rooms."
Reviewed on Aug 6, 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.
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- Hotels near Indigo's Family Fun Center
- Hotels near Indigo's Billiards
- Hotels near Rotary Park
- Hotels near Theatre Winter Haven
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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.