Where to stay around Winter Haven?

Our 2018 accommodation listings offer a large selection of 1,972 holiday lettings near Winter Haven. From 1,089 houses to 689 villas, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Winter Haven is on HomeAway.

What is the best area to stay when travelling to Winter Haven?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Winter Haven:

  • Highlands Reserve: 2,526 holiday homes
  • Calabay Parc: 548 holiday homes
  • Lake Berkley: 1,518 holiday homes
  • Cumbrian Lakes: 262 holiday homes
  • Southern Dunes: 413 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday rentals available.

What are the most popular points of interest and landmarks to stay near when travelling to Winter Haven?

HomeAway offers a large selection of holiday accommodations near great places in Winter Haven. From HomeAway travellers, the most popular points of interest to stay near are:

  • Winter Haven Station: 8,647 holiday lettings
  • Cypresswood Golf and Country Club: 11,920 holiday lettings
  • Indigo's Family Fun Center: 9,232 holiday lettings
  • Disney World: 35,587 holiday lettings
  • ChampionsGate Golf Club: 35,127 holiday lettings

But there are many other points of interest around Winter Haven listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent houses in Winter Haven?

Yes, of course. HomeAway offers 1,089 houses in Winter Haven. Our other popular types of Winter Haven holiday rentals include:

  • Villas: 689 self catering accommodations
  • Condos: 74 self catering accommodations
  • Apartments: 11 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including mobile homes and more.

Can I find a holiday accommodation with pool in Winter Haven?

Yes, you can select your preferred holiday accommodation with pool among our 1,502 holiday homes with pool available in Winter Haven. Please use our search bar to access the selection of holiday rentals available.

    Make a holiday villa in Winter Haven your home away from home

    About as central as it's possible to get in Florida, Winter Haven holiday villas and apartments put you bang in the middle of the Sunshine State. As an absolute mecca for waterskiing enthusiasts, the area is riddled with over 50 lakes, interconnected by man-made canals; it's a positive nirvana for water sports. Holiday accommodation in Winter Haven are all fully air-conditioned, with all the modern appliances to keep your stay free of hassle. Nearly all Winter Haven rentals have access to a pool and welcome children, though only a few are accessible via wheelchair.

    Things to do

    -Theme parks: Opening just a couple of years ago on the site that was formerly Cypress Gardens, one of the world's first theme parks, Legoland Florida is a great family attraction. Legoland's 145 acres of park host over 50 Lego-themed rides, shows and attractions, as well as the preserved botanical garden area built by the former resident.

    -Lakes: Winter Haven calls itself 'The Chain of Lakes City', and it's easy to see why. By far the most prominent features surrounding your Winter Haven holiday accommodation are the lakes and interconnecting waterways; teeming with wildlife, this is one of the world's premier bass fishing destinations, too.

    -Watersports: With so many lakes, watersports are Winter Haven's raison d'etre. Cypress Gardens was instrumental in the invention of the sport of waterskiing, so the facilities for getting wet, and the variety of ways of doing so, are myriad. Rentals at Winter Haven are never far from the opportunity.

    -Nightlife: There are far more bars and restaurants than needed to cater to a town of 26,000, which tells you all you need to know about Winter Haven's popularity as a holiday resort. From fast food to fine dining, laid-back pubs to energetic dance halls, there's something for everyone.

    -Beaches: There's not much in the way of sandy beaches in this lake-strewn area, but either coast is only an hour away by car. From the amazing beaches at Tampa Bay in the west, to the equally pristine sand and surf of the Atlantic Space Coast, you're spoiled for choice.

    Weather in Winter Haven

    You could expect Florida's subtropical climate to be the hottest here, which is about as far from the sea as you can get in Florida. Fortunately, the extensive wetlands have a similar moderating influence, so temperatures in the summer rarely get intolerable. Typical highs don't exceed the mid-30°C mark, and this is further tempered by the summer thunderstorms which tend to cool things down a little. Winters are on a par with the British summer, so temperatures top 20°C and rainfall is infrequent at best.

    Travel to Winter Haven

    As close as Winter Haven is to Orlando and Tampa, it would be silly to fly into anywhere else, at only 48 and 59 miles away respectively. Public transport tends to be a bit of a joke in the US, and the automobile reigns supreme, so flying and driving a hire car is really the most effective, and cheapest, option. There is an Amtrak station in Winter Haven, however, which gives you the chance to experience an authentic American train trip, but they're somewhat unreliable when it comes to timetables. Nearby Lakeland has the only Greyhound station.

    Attractions in and around Winter Haven

    Have time to spare and looking for things to do around Winter Haven? Local attractions include Legoland Florida and Indigo's Family Fun Center. Visitors searching for nearby cultural experiences can spend an enlightening afternoon at Polk Museum of Art, Polk County Historical Museum or Fantasy of Flight. Plan to attend a game or event? Get tickets for Chain of Lakes Park or Publix Field at Joker Marchant Stadium. ChampionsGate Golf Club and The Circle B Bar Reserve are just a couple of activities around the area. Also while in town, you can visit Willowbrook Golf Course, Cypresswood Golf and Country Club or Lake Henry Golf Club.