Destination guide

Wonderful times in Winter Haven

Let Winter Haven vacation rentals welcome you to this year-round destination. Let your imagination run wild in LEGOLAND Florida Resort or go wild in the water in one of Winter Haven’s 50 lakes. Catch the community theater bug by taking in a show at the Theatre Winter Haven. If you’re really looking for some retail therapy, step back in time and explore the many antiques stores that call Winter Haven home. However you want to spend your vacation, Winter Haven is sure to have something to satisfy everyone.

Things to do

Theme park and theater thrills in Winter Haven

Adults and children alike will love LEGOLAND Florida Resort! This 150-acre theme park is dedicated to family-friendly fun and will delight children of all ages. Make a splash in the adjoining water park for an additional fee, and cool off in the Floridian sun. After a day of fun in the sun, returning to the Winter Haven vacation rentals will always be welcome; but how about an evening at the theater? Theatre Winter Haven is locally renowned for its top-quality community theater. The program will, of course, depend on when you visit, but you’re guaranteed a great evening.


Wild water and amazing antiques in Winter Haven

Winter Haven is also known as “The Chain of Lakes City” and for good reason. After getting settled in Winter Haven vacation rentals, break out your bathing suit and head for one of the city’s 50 lakes! Flyboarding is one of the area’s popular water pursuits and you can book a lesson with companies operating from different lakes. Want something a bit more sedate on the water? Charter a boat and spend an afternoon bobbing on the waves while bass fishing. On land, eagle-eyed antiques enthusiasts will love browsing for souvenirs and gifts in the many antiques stores here.


It’s not called Winter Haven for nothing!

If you’re looking for year-round sunshine and warm temperatures, Winter Haven is the perfect place for you. July through August see average highs in the low 90s but also a lot of rain owing to the humid, subtropical Floridian climate. For those looking to avoid the rain, come to Winter Haven from October through May as these are by far the driest months. Winters see average highs in the high 40s so you can expect to get your fill of this town’s average 242 days of sunshine.

Natural features

Love the lakes in Winter Haven

Located between Tampa and Orlando within the Central Florida Highlands, Winter Haven is not your typical Floridian beach-side community. You’ll see flatland with rolling hills all around you, as well as the lakes this city is so famous for. The lakes are full of wildlife, and nature lovers may be able to spot bald eagles and alligators as well as the bass. To get a real sense of the natural world, sit back and relax on a guided river tour and learn all about the birds and creatures that call Winter Haven home.

How to get there

How to get to and around Winter Haven

The nearest airport is in Kissimmee, FL (ISM-Kissimmee Gateway), located 25.9 mi (41.8 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Tampa, FL (TPA-Tampa Intl.), which is 49.1 mi (79.1 km) away.

If you'd prefer to travel by train, the main station is Winter Haven Station.

Can I find a vacation rental around Winter Haven?

Yes, our 2019 property listings offer a large selection of 1,479 vacation rentals near Winter Haven. From 715 Houses to 58 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Winter Haven for a holiday or a weekend are on HomeAway.

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

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Winter Haven:

  • Champions Gate: 6,850 vacation rentals
  • Regal Palms: 2,178 vacation rentals
  • Bahama Bay: 822 vacation rentals
  • Highlands Reserve: 2,586 vacation rentals
  • Orange Lake: 703 vacation rentals

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

What are the popular points of interest near where I can stay when traveling to Winter Haven?

HomeAway offers a large selection of vacation rentals near lovely places in Winter Haven. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Legoland Florida: 32,139 vacation rentals
  • Winter Haven Station: 11,350 vacation rentals
  • Chain of Lakes Park: 11,340 vacation rentals
  • Cypresswood Golf and Country Club: 14,494 vacation rentals
  • Lake Henry Golf Club: 34,111 vacation rentals

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 vacation rentals available near the point of interest of your choice.

Can I rent Houses in Winter Haven?

Yes, of course. HomeAway has 715 Houses in Winter Haven. Our other popular types of vacation rentals in Winter Haven include:

  • Condos/Apartments: 58 rentals available
  • Villas: 539 rentals available
  • Townhouses: 133 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Winter Haven?

Yes, you can select your preferred vacation rental with pool among our 1,295 vacation rentals with pool available in Winter Haven. Please use our search bar to access the selection of vacation rentals available.

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