Find luxury hotels in Winter Haven, FL

Expedia can help you arrange a flight to Kissimmee, FL (ISM-Kissimmee Gateway) airport or Avon Park, FL (AVO-Avon Park Executive) airport, and then you can select from various places to stay that will deliver the luxury you’d like to find. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay special. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can help you find the best luxury hotel experience that Winter Haven has to offer. Known for its entertainment and sporting events, Winter Haven also has some interesting things to see and do including LEGOLAND® Florida, so you may want to take in the local sights during your visit.

Lie in the lap of luxury during your getaway to Winter Haven in one of Expedia’s 12 luxury hotels.

Planning for the weather is an important factor for making your trip to Winter Haven a success, especially when you’re splurging. The hottest months are usually August and July, with an average temperature of 27°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Haven are August, July, September and June, with each month seeing an average of 211 mm of rainfall.

Take in the sights and attractions that Winter Haven offers with a visit to LEGOLAND® Florida, Theatre Winter Haven and Chain of Lakes Park. If you have extra time while you’re in the area, you might want to stop by The Circle B Bar Reserve and Indigo’s Family Fun Center.

It’s easier to get around town comfortably when you know your options. If you want to venture outside the area, take a train from Winter Haven Station.