Book Cheap Hotels in Winter Haven

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Most frequently booked Winter Haven hotels

Best Western Plus Winter Haven Inn & Suites

5801 Roosevelt Dr Winter Haven FL

Free cancellation

Reserve now, pay when you stay

5.51 km from city centre

CA $186

CA $208 total

Dec 21 - Dec 22

includes taxes & fees

Book a stay at this business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LEGOLAND® Florida and Peppa Pig Theme Park Florida are located nearby.

Pool

Breakfast included

Legoland Florida Hotel

1 Legoland Way Winter Haven FL

5.21 km from city centre

CA $510

CA $625 total

Dec 9 - Dec 10

includes taxes & fees

Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions LEGOLAND® Florida and Peppa Pig Theme Park Florida are located nearby.

Pool

Breakfast included

Staybridge Suites Winter Haven Auburndale by IHG

305 5th St NW and Avenue D NW Winter Haven FL

Free cancellation

0.4 km from city centre

CA $209

CA $234 total

Jan 5 - Jan 6, 2026

includes taxes & fees

Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LEGOLAND® Florida and Winter Haven Public Library are located nearby.

Pool

Breakfast included

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

Free cancellation

Reserve now, pay when you stay

38.43 km from city centre

CA $206

CA $308 total

Dec 9 - Dec 10

includes taxes & fees

Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Pool

Hot tub

Holiday Inn Resort Kissimmee by the Parks by IHG

3011 Maingate Ln Kissimmee FL

Free cancellation

37.71 km from city centre

CA $104

CA $145 total

Dec 15 - Dec 16

includes taxes & fees

Book a stay at this family-friendly hotel in Kissimmee. Enjoy free parking, 2 outdoor pools, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.

Pool

Hot tub

Margaritaville Resort Orlando

8000 Fins Up Circle Kissimmee FL

Free cancellation

Reserve now, pay when you stay

37.6 km from city centre

CA $171

CA $270 total

Dec 9 - Dec 10

includes taxes & fees

Book a stay at this spa resort in Kissimmee. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Pool

Hot tub

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy Kissimmee FL

Free cancellation

Reserve now, pay when you stay

37.53 km from city centre

CA $63

CA $126 total

Dec 10 - Dec 11

includes taxes & fees

Stay at this resort in Kissimmee. Enjoy free WiFi, 2 hot tubs, and 2 outdoor pickleball courts. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.

Pool

Hot tub

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

Free cancellation

Reserve now, pay when you stay

35.53 km from city centre

CA $135

CA $200 total

Dec 14 - Dec 15

includes taxes & fees

Book a stay at this golf property in Kissimmee. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the pool and the restaurant in our reviews. Popular attractions ESPN Wide World of Sports Complex and Disney's Animal Kingdom® Theme Park are located nearby.

Pool

Parking included

Comfort Inn & Suites Kissimmee by the Parks

7675 W Irlo Bronson Hwy Kissimmee FL

Free cancellation

Reserve now, pay when you stay

37.6 km from city centre

CA $88

CA $128 total

Dec 17 - Dec 18

includes taxes & fees

Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.

Pool

Hot tub

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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.

Top family friendly Winter Haven hotel deals

Howard Johnson by Wyndham Winter Haven FL

1300 3rd St Winter Haven FL

CA $117

CA $132 total

Dec 11 - Dec 12

includes taxes & fees

6.8/10 (1,016 reviews)

Top cheap Winter Haven hotel deals

Howard Johnson by Wyndham Winter Haven FL

1300 3rd St Winter Haven FL

CA $117

CA $132 total

Dec 11 - Dec 12

includes taxes & fees

6.8/10 (1,016 reviews)

Top hotels in Winter Haven for Extended Stay

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

100 Orlando Breeze Circle Davenport FL

CA $135

CA $176 total

Dec 11 - Dec 12

includes taxes & fees

9.2/10 Wonderful! (498 reviews)

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.

Winter Haven hotels essential information

Accommodation	39,414 hotels
Lowest Price	CA $104
Highest Price	CA $625
Popular hotels	Best Western Plus Winter Haven Inn & Suites , Legoland Florida Hotel, Staybridge Suites Winter Haven Auburndale by IHG, The Grove Resort & Water Park Orlando, Holiday Inn Resort Kissimmee by the Parks by IHG, Margaritaville Resort Orlando, Kompose Boutique Resort at Theme Parks, Hilton Vacation Club Mystic Dunes Orlando, Comfort Inn & Suites Kissimmee by the Parks

Frequently asked questions

What are the top kid-friendly hotels in Winter Haven?

Take some of the trials out of traveling with young ones by booking a family-friendly Winter Haven hotel. From entertaining amenities to more services, these properties come with perks that'll make your trip run smoothly: Unpack your bags at FALL/WINTER SPECIAL RATES Mid-century Mod w/ Fireplaces - Downtown Near Legoland. It comes with a water park, a swimming pool and a talent for making families feel welcome. Otherwise, spend your Winter Haven getaway at Budget Inn Winter Haven. Make the most of a picnic area, front desk services and more here.

Where can I find cheap hotels in Winter Haven?

At Travelocity you'll find really nice hotels in Winter Haven at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winter Haven rather than in Winter Haven. We may find you even better rates, too.

How do I find the best Winter Haven hotel deals?

Simple! On Travelocity, look through the fantastic offers we've already found in Winter Haven then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.

How much does it cost to stay in a hotel in Winter Haven?

The cheapest hotel in Winter Haven is CA $104 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.

How many hotels are in Winter Haven?

There are 39,414 hotels in Winter Haven on Travelocity.

What are the best hotels in Winter Haven?

Winter Haven has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winter Haven for you!

When is the best time to visit Winter Haven?

If you want the joy of a fun-filled trip in peak season, visit Winter Haven during February, March and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as January, September and October.

When is the cheapest time to stay in Winter Haven?

Based on historic data is usually the cheapest month to visit Winter Haven. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.

Are there any great family-friendly hotels in Winter Haven?

There are multiple hotels in Winter Haven that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winter Haven. We have plenty of kid-friendly hotels in Winter Haven to choose from on Travelocity!

Why book a hotel in Winter Haven through Travelocity?

Because we have the top hotels in Winter Haven! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!

How do I cancel my hotel booking in Winter Haven on Travelocity?

Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.