
Winter Haven Holidays
- Plan, book, travel with confidence
Better together
Save up to €185 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Winter Haven
Price found within the past 48 hours. Click for updated prices.

Spark by Hilton Sarasota Siesta Key Gateway
per person
12 Sept - 15 Sept
found 10 hours ago
Return flight included
Providence (PVD) to Tampa (TPA)
8.4/10 Very Good! (1,506 reviews)
Location was good.
The sink was totally clogged when we got there but was fixed after we complained. The seal around the toilet was slowly leaking. The shampoo bottle fell off the wall. The bedding was was old and worn. This place could sure use a lot of little updates.
Reviewed on 9 Aug 2025


Siesta Key Palms Resort
Save 100% on your flight
per person
12 Sept - 15 Sept
found 10 hours ago
Return flight included
Providence (PVD) to Tampa (TPA)
9.2/10 Wonderful! (1,004 reviews)
The property was very unique with the landscape being sand. There were hammocks all around little fire pits here and there and it was quiet. The place was very clean easy to get to places we will definitely be back.
Reviewed on 8 Aug 2025

Top hotels in Winter Haven

Staybridge Suites Winter Haven Auburndale by IHG
305 5th St NW and Avenue D NW, Winter Haven, FL
Fully refundable
The price is €122 per night from 21 Aug to 22 Aug
€122
21 Aug - 22 Aug
includes taxes & fees
9.6/10 Exceptional! (483 reviews)
"Beautiful rooms"
Reviewed on 5 Aug 2025

Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard, Winter Haven, FL
Fully refundable
The price is €89 per night from 17 Aug to 18 Aug
€89
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 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 6 Aug 2025

Best Western Plus Winter Haven Inn & Suites
5801 Roosevelt Dr, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is €122 per night from 17 Aug to 18 Aug
€122
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (937 reviews)
"Great location. Great staff.. Clean, modern spacious rooms."
Reviewed on 6 Aug 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.
Popular places to visit

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.
Lake Henry Golf Club
Enjoy a round of golf in Winter Haven at Lake Henry Golf Club. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.
Sertoma Park
Sertoma Park is just one of the places to see in Winter Haven, so why not enjoy the other things to explore during your travels? Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.
Frequently asked questions
More trip options
Expedia's Latest Trends
Flights
Activities
Holiday Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.