Winter Haven Vacations from $349
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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
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (574 reviews)
The room was great: looked updated recently, quiet, plenty of room, very well maintained and included small things like washing machine soap. The pool was nice and included some pool toys. The restaurant/bar was convenient but wished it had more food options. The lobby was a hallway with a small desk as the check-in counter. We did have some "fear" once we came into the check-in area.. like what did we get ourselves into but the property was very clean, friendly staff and the room did not disappoint. The property is more of suite/vacation rental than a hotel but in a great way.
Reviewed on Aug 16, 2025
La Tortuga
Pass-a-Grille
Save 100% on your flight
per person
Oct 16 - Oct 20
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (29 reviews)
Very beautiful. Quiet. Easy check in/ out. Would stay again. Only complaint is walls are thin, can hear your neighbors.
Reviewed on Apr 11, 2025
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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.
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.
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 19 to Aug 20
$142 total
Aug 19 - Aug 20
Total includes taxes and fees
9.6/10 Exceptional! (498 reviews)
"Clean, like new, friendly staff, beautiful large room, comfy beds"
Reviewed on Aug 12, 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 24 to Aug 25
$104 total
Aug 24 - Aug 25
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
$116 nightly
The price is $130 total per night from Aug 17 to Aug 18
$130 total
Aug 17 - Aug 18
Total includes taxes and fees
9.4/10 Exceptional! (946 reviews)
"Exelent"
Reviewed on Aug 12, 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
- Hotels near Winter Haven Station
- Hotels near Inman Park
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- Hotels near Sertoma Park
- Hotels near LEGOLAND® Florida
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- Cabin Rentals in Eloise
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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.