Where to stay around Winter Garden, FL?

Our 2019 property listings offer a large selection of 34,541 vacation rentals near Winter Garden. From 11,697 Villas to 11,483 Houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Winter Garden for a holiday or a weekend are on VRBO.

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

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 Garden:

  • Vista del Lago: 402 vacation rentals
  • Regal Palms: 2,526 vacation rentals
  • Terra Verde Resort: 1,757 vacation rentals
  • Watersong: 915 vacation rentals
  • West Haven: 5,125 vacation rentals

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

Can I rent Villas in Winter Garden?

Yes, of course. VRBO has 11,697 Villas in Winter Garden. Our other popular types of vacation rentals in Winter Garden include:

  • Houses: 11,483 rentals available
  • Townhouses: 4,915 rentals available
  • Condos/Apartments: 4,457 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 Garden?

Yes, you can select your prefered vacation rental with pool among our 32,084 vacation rentals with pool available in Winter Garden. Please use our search bar to access the selection of vacation rentals available.

    Family enjoyments in Winter Garden

    Winter Garden's citrus tree-peppered avenues and old blocks dating back to the days of the Orange Belt Railway make a great place to come for a relaxed and wholesome slice of the Sunshine State. Historic districts and rejuvenated boxcar depots mingle on the sidewalks, there are nostalgic theater houses, intriguing museums that spin tales of Floridian history, and oodles of Winter Garden vacation rentals that are great for the whole family. And talking of family, there are enjoyments for the gang just a little to the east – think Cinderella's Castle, Big Thunder Mountain, and the Wizarding World of Harry Potter.

    Living like a local in Winter Garden

    Walk your way around the old Downtown of Winter Garden to spy out the historic relics of its railroad past – you can even get guided tours of the place to really delve into the heritage. Then, make for the weekly farmer's market to shop for fresh fruit and Floridian produce in the company of locals, or hop between the independent cafes and microbreweries learning the ins and outs of bean roasting and beer tasting. When evening comes, the whole of Plant Street buzzes with life, whether that means summertime jazz sessions or fine-dining in the bistros there.

    West Orange history and wild rides in Winter Garden

    Quaint little Winter Garden has its own clutch of intriguing attractions. There's the Winter Garden Heritage Foundation, which chronicles the rich culture of West Orange. There's the Central Florida Railroad Museum with its old tracks and platforms. There's the Garden Theatre, dating back to the 1930s. Winter Garden vacation rentals close to Walt Disney World offer a whole other bunch of delights. Rollercoasters and rides aplenty can be expected, from the sloshing wave pools of Typhoon Lagoon to the dusty savannahs of the wild Animal Kingdom and beyond.

    Visit Winter Garden any time of year

    Winter Garden sits on the cusp of the Florida tropics, bathed in sun for much of the year but also weathering a wet and humid rainy season from around May to October. Most visitors come in the summer vacation period and around Christmas, but you might do better holding off to book those Winter Garden vacation rentals for when the crowds have dispersed. Months like November, February, March, and April often offer the perfect balance between price and sunshine, not to mention fewer folk queuing in the Disney resorts.

    Birds and lakes in Winter Garden

    Winter Garden is enfolded by the soft lowlands of central Florida. It can be found clutching the western fringes of Orlando, where it spreads out along the banks of Lake Apopka. It's the north shore – now a protected reserve – of that where the wilder side of things start in earnest. There, you can spot alligators crossing the roadways, more than 350 species of bird life, and pretty dashes of marshland to boot. In the other direction is the Lake Louisa State Park, where submerged forests hide gopher tortoises, bald eagles, and giant cypress trees.

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