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Top Rated Winter Haven Hotels

Estimated price for 1 night/2 adults

Courtyard by Marriott Winter Haven
Courtyard by Marriott Winter Haven
3.0 out of 5.0 6225 Cypress Gardens Boulevard SE, Winter Haven, FL
Free Cancellation
$119
4.7/5 (3 reviews)

It was great! Beautiful property and very clean and new

Reviewed on Mar 15, 2019
Situated in Winter Haven, this hotel is 0.8 mi (1.2 km) from Legoland Florida and within 6 mi (10 km) of Chain of Lakes Park and Indigo's Family Fun Center. ...
Legoland Beach Retreat
Legoland Beach Retreat
3.5 out of 5.0 LEGOLAND WAY,100, Winter Haven, Florida
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4.6/5 (8 reviews)

I loved this place, kids had such a good time they didn’t want to leave. It was very the long drive to get there.

Reviewed on Apr 26, 2019
Situated in Winter Haven, this hotel is 0.3 mi (0.4 km) from Legoland Florida and within 6 mi (10 km) of Chain of Lakes Park and Indigo's Family Fun Center. ...
Hampton Inn Winter Haven
Hampton Inn Winter Haven
2.5 out of 5.0 202 Cypress Gardens Blvd, Winter Haven, FL
Free Cancellation
$137
4.1/5 (19 reviews)

New rooms Great location Excellent service Good breakfast

Reviewed on May 20, 2019
Located in the heart of Winter Haven, this hotel is within 1 mi (2 km) of Indigo's Family Fun Center and Chain of Lakes Park. Legoland Florida and Lake Conine ...
Holiday Inn Winter Haven
Holiday Inn Winter Haven
3.0 out of 5.0 200 Cypress Gardens Boulevard, Winter Haven, FL
Free Cancellation
$99
4.0/5 (18 reviews)

The Manager, Dezzy, and her staff, including Katrina, Jada, Susan and Susan and so many others, went way above and beyond for our stay! I thank them all so much! 5 STARS! The only issue I had was with the sports teams of teenagers were a little a loud, but I remember being a kid in a hotel LOL I ...

Reviewed on May 6, 2019
Located in the heart of Winter Haven, this hotel is within 1 mi (2 km) of Indigo's Family Fun Center and Chain of Lakes Park. Legoland Florida and Lake Conine ...
Quality Inn & Suites Conference Center
Quality Inn & Suites Conference Center
2.5 out of 5.0 5665 Cypress Gardens Boulevard, Building A, Winter Haven, FL
Free Cancellation
$76
4.0/5 (1 reviews)
Situated in Winter Haven, this motel is 0.5 mi (0.7 km) from Legoland Florida and within 6 mi (10 km) of Chain of Lakes Park and Indigo's Family Fun Center. ...
Lake Roy Beach Inn
Lake Roy Beach Inn
2.0 out of 5.0 1823 Cypress Gardens Blvd, Winter Haven, FL
$78
3.5/5 (25 reviews)

The lake is beautiful. The condition of the building is it is in great need of upgrading and maintenance. The hotel door to our room didn’t feel safe, it was chintzy. Breakfast is fake eggs, margarine, and terrible tasting grits. I couldn’t eat anything but the fruit. But the bed is comfortable. ...

Reviewed on Dec 28, 2018
Located in the heart of Winter Haven, this hotel is 1.7 mi (2.7 km) from Legoland Florida and 1.9 mi (3.1 km) from Chain of Lakes Park. Indigo's Family Fun Center ...
Howard Johnson by Wyndham Winter Haven FL
Howard Johnson by Wyndham Winter Haven FL
2.0 out of 5.0 1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
Free Cancellation
$80
3.0/5 (47 reviews)

Decent place. Would stay there again. Right up the road from LEGO land. Over all good experience.

Reviewed on May 13, 2019
Situated in the business district, this motel is within a 15-minute walk of Indigo's Family Fun Center and Chain of Lakes Park. Lake Conine is 2.9 mi (4.7 km) ...
Winter Haven Gardens Inn and Banquet Center
Winter Haven Gardens Inn and Banquet Center
2.5 out of 5.0 1150 3rd Street SW, Winter Haven, FL
Free Cancellation
$47
2.5/5 (32 reviews)

It was pleasingly nice, rooms need an upgrade. Staff was nice and friendly.

Reviewed on Jun 3, 2019
Situated in Winter Haven, this hotel is within 1 mi (2 km) of Indigo's Family Fun Center and Chain of Lakes Park. Lake Conine is 2.8 mi (4.6 km) away. Winter ...
Econo Lodge
Econo Lodge
2.0 out of 5.0 5665 Cypress Gardens Boulevard, Building b, Winter Haven, FL
Free Cancellation
$55
2.4/5 (38 reviews)

Nice place to stay for the money , close to Legoland

Reviewed on Apr 27, 2019
Situated in Winter Haven, this hotel is 0.4 mi (0.6 km) from Legoland Florida and within 6 mi (10 km) of Chain of Lakes Park and Indigo's Family Fun Center. ...

Luxury Hotels in Winter Haven

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Estimated price for 1 night/2 adults

Pet Friendly Winter Haven Hotels

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Estimated price for 1 night/2 adults

Finding a Hotel in Winter Haven


So you're thinking about a getaway to Winter Haven? If you want a place to call home that's located near some well-known Winter Haven attractions such as Legoland Florida, just go to Orbitz, choose your travel dates, and voilà! Review the list of hotels and other accommodations to find those that are located near everything you want to see.


Whether you want to find a bed and breakfast or an affordable hotel, Winter Haven has 40 places you can stay including:

  • 8 hotels
  • 8 condos
  • 7 motels

We make it easy to find a convenient flight into Kissimmee, FL (ISM-Kissimmee Gateway), which is 25.9 mi (41.8 km) from the heart of the city. Find your ideal flight quickly by using the filters on our site to narrow down your search.


Accommodations in Winter Haven


Orbitz can help you find lodging that has all the amenities you want in a hotel, whether that's free parking, a kitchen, or a pool.

If you want a quick bite before hitting the trail to explore your surroundings, think about one of these Winter Haven properties, known for their free breakfast:

  • Winter Haven Gardens Inn and Banquet Center
  • Lake Roy Beach Inn
  • Rodeway Inn and Suites

Go for a swim when you stay at one of these Winter Haven properties, popular for their pools.

  • Econo Lodge
  • Travelodge by Wyndham Winter Haven
  • Legoland Hotel

What's the Weather Like in Winter Haven?


Debating whether you're going to need socks with your sandals while you're here? Winter Haven is typically warmest in August and July, while it’s usually the chilliest in January and December. The rainiest months are July and June, while the driest months are normally November and January. Here's a rundown of rain and seasonal temperatures so you're ready for everything Mother Nature can deliver:


  • January to March: average temp during the day is 81°F and 51°F at night
  • April to June: average temp during the day is 92°F and 60°F at night
  • July to September: average temp during the day is 93°F and 71°F at night
  • October to December: average temp during the day is 88°F and 51°F at night
  • Annual rainfall average: 51.18 inches

Things to See and Do in Winter Haven


Stop in for a snack at one the restaurants in family-friendly Winter Haven, and then enjoy the local culture such as the entertainment. Take in these notable tourist attractions during your trip:

  • Legoland Florida
  • Indigo's Family Fun Center
  • Chain of Lakes Park
  • Willowbrook Golf Course
  • Cypresswood Golf and Country Club
  • Lake Henry Golf Club

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