Winter Haven Vacations from $287
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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.
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,007 reviews)
The staff was very nice and helpful. The shuttle would take you anywhere within 3 miles. Pool was nice and the hotel was quiet.
Reviewed on Aug 12, 2025
Mar Bay Motel &Suites
Save 100% on your flight
per person
Sep 21 - Sep 27
found 22 hours ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
8.6/10 Excellent! (59 reviews)
Close to downtown safety harbor, oldsmar and Clearwater, the perfect retreat being close to everything but not in the heart of it all.
Reviewed on May 12, 2025
Clearwater Suites
Save 100% on your flight
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (12 reviews)
The property is spacious, beds are comfortable, staff are friendly. Located just a block away from the beach. Guest service desk provided a welcome snack basket. The one downside is that the bathroom could be cleaned better. Overall it’s a great place to stay in.
Reviewed on Aug 16, 2025
The Westin Sarasota
Central Sarasota
Save 100% on your flight
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,057 reviews)
It was a really unique building, very beautiful design all throughout. Our room was wonderful and very clean everyday. Our only complaint was with the parking situation. It was very expensive to park at the property and we felt ill informed about the parking situation in the area.
Reviewed on Aug 18, 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 21 to Aug 22
$142 total
Aug 21 - Aug 22
Total includes taxes and fees
9.6/10 Exceptional! (503 reviews)
Good Breakfast!
"Excellent hotel! Very clean and Breakfast is amazing!!!"
Reviewed on Aug 16, 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 Sep 7 to Sep 8
$104 total
Sep 7 - Sep 8
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
$115 nightly
The price is $128 total per night from Aug 19 to Aug 20
$128 total
Aug 19 - Aug 20
Total includes taxes and fees
9.4/10 Exceptional! (948 reviews)
"Room was spacious and clean. Breakfast was good. Very close to Legoland. Staff was great"
Reviewed on Aug 15, 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
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- Hotels near Sertoma Park
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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.