Where to stay around Winter Haven, FL?

Our 2019 property listings offer a large selection of 2,043 vacation rentals near Winter Haven. From 1,096 Houses to 682 Villas, 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 VRBO.

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:

  • Regal Palms: 2,548 vacation rentals
  • Watersong: 918 vacation rentals
  • West Haven: 5,120 vacation rentals
  • Highlands Reserve: 3,017 vacation rentals
  • Sandy Ridge: 1,689 vacation rentals

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

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

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

  • Winter Haven Station: 10,107 vacation rentals
  • Indigo's Family Fun Center: 10,790 vacation rentals
  • Cypresswood Golf and Country Club: 13,549 vacation rentals
  • Chain of Lakes Park: 10,094 vacation rentals
  • Willowbrook Golf Course: 28,079 vacation rentals

But there are many other points of interest around Winter Haven listed on VRBO 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. VRBO has 1,096 Houses in Winter Haven. Our other popular types of vacation rentals in Winter Haven include:

  • Villas: 682 rentals available
  • Townhouses: 113 rentals available
  • Condos/Apartments: 96 rentals available

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

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

Yes, you can select your prefered vacation rental with pool among our 1,858 vacation rentals with pool available in Winter Haven. Please use our search bar to access the selection of vacation rentals available.

    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.

    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.

    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.

    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.

    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.

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