Winter Haven Vacations from $448
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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.
Mar Bay Motel &Suites
Save 100% on your flight
Price was $841, price is now $448 per person
$448
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $949, price is now $491 per person
$491
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,000 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
FUSION Resort Waterfront Suites
Save 100% on your flight
Price was $1,221, price is now $679 per person
$679
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,049 reviews)
Rooms are 2 bedroom suites. Full size kitchen makes an extended stay more affordable. Extremely pet friendly environment.
Reviewed on Aug 8, 2025
Ocean Club Treasure Island Hotel
Save 100% on your flight
Price was $1,805, price is now $1,024 per person
$1,024
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (598 reviews)
Love this place! Rooms are excellent. Please note the lobby is a tiny check in area but the rooms are amazing.
Reviewed on Aug 20, 2025
Clearwater Suites
Save 100% on your flight
Price was $998, price is now $568 per person
$568
per person
Oct 13 - Oct 20
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
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See all available trips from San Antonio to Winter Haven
View all tripsDiscover the most popular places to visit in Winter Haven
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 27 to Aug 28
$142 total
Aug 27 - Aug 28
Total with taxes and fees
9.6/10 Exceptional! (515 reviews)
"Was very clean and accommodating. Had plenty of amenities including, pool, great full breakfast, complimentary laundry room, and full kitchens."
Reviewed on Aug 23, 2025
Best Western Plus Winter Haven Inn & Suites
5801 Roosevelt Dr, Winter Haven, FL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $132 total per night from Aug 25 to Aug 26
$132 total
Aug 25 - Aug 26
Total with taxes and fees
9.4/10 Exceptional! (958 reviews)
"Always stay at this hotel when we go to legoland. Breakfast is good, very clean, and service is good. Would recommend"
Reviewed on Aug 21, 2025
Legoland Florida Hotel
1 Legoland Way, Winter Haven, FL
$264 nightly
The price is $296 total per night from Aug 27 to Aug 28
$296 total
Aug 27 - Aug 28
Total with taxes and fees
9/10 Wonderful! (17 reviews)
"Great experience"
Reviewed on Aug 18, 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
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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.