Winter Haven Holidays

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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

Spark by Hilton Sarasota Siesta Key Gateway

3 out of 5
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

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
per person
12 Sept - 15 Sept
found 10 hours ago
Return flight included
Providence (PVD) to Tampa (TPA)
8.6/10 Excellent! (2,157 reviews)
Bed comfort , great location, friendly staff.

Reviewed on 6 Aug 2025

Siesta Key Palms Resort

Siesta Key Palms Resort

3.5 out of 5
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

Luxury Pool Retreat near Siesta Key

Luxury Pool Retreat near Siesta Key

2 out of 5
per person
12 Sept - 15 Sept
found 10 hours ago
Return flight included
Providence (PVD) to Tampa (TPA)
10/10 Exceptional! (2 reviews)
Great property. Definitely worth the price

Reviewed on 21 Jul 2025

Beautiful Pool Home Near Siesta Key Beach 2 Bedroom Home

Beautiful Pool Home Near Siesta Key Beach 2 Bedroom Home

3 out of 5
Gulf Gate Estates
per person
12 Sept - 15 Sept
found 10 hours ago
Return flight included
Providence (PVD) to Tampa (TPA)
10/10 Exceptional! (1 review)
We have an amazing family time in this beautiful house

Reviewed on 13 May 2025

Top hotels in Winter Haven

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

3 out of 5
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

Staybridge Suites Winter Haven Auburndale by IHG
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
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

Holiday Inn Winter Haven by IHG
Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

3.5 out of 5
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

Best Western Plus Winter Haven Inn & Suites 
See all 38,265 properties in Winter Haven
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 featuring a river or creek, a pond and rides

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.

LEGOLAND® Florida

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.

Lake Henry Golf Club

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.

Sertoma Park

Frequently asked questions

How much does a Winter Haven holiday package cost?
You'll find cheap prices from €222 on Expedia for your Winter Haven getaway. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Winter Haven costs.
What are the cheapest months to go to Winter Haven?
You can generally find reduced prices and better availability in September, October and November. Explore our cheap Winter Haven holiday packages and you could get some great off-season discounts.
How many days is enough for Winter Haven?
Dedicate around 2 days for your Winter Haven holiday if you're hoping to enjoy everything that makes this place unique. Stroll around popular neighbourhoods, including Cypress Gardens and Jan Phyl Village. Then tick off top attractions like Indigo's Billiards, Bowling & Games and Indigo's Family Fun Centre. With a good itinerary, you'll be kept busy with room for some downtime too. Want to travel outside of Winter Haven? Consider fitting in a day trip or two.
Is it worth booking a holiday package to Winter Haven?
Popular for its fishing, walking trails and golfing, a Winter Haven holiday is a hit with all kinds of visitors. Be sure to check out top sights like Chain of Lakes Park and Theatre Winter Haven, and consider renting a set of wheels for day trips to explore even more.
How to find the best Winter Haven package deals?
Use Expedia's filters to find some of the best Winter Haven package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Winter Haven package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Winter Haven holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can tailor your Winter Haven trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Winter Haven?
Score incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Winter Haven getaway.
How to plan a trip to Winter Haven?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Winter Haven.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to save for your trip to Winter Haven. Then, pick a hotel that matches your budget, whether that's an affordable option or a lavish retreat.
  3. Determine how many days away: Start by compiling a list of the activities and attractions you want to experience in Winter Haven. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customised Winter Haven holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.