Discover a selection of more than 10,000 vacation rentals in Winter Garden that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including private pools and swimming pools. Prices start at $76 per night, and houses and villas are popular options for a stay in Winter Garden. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Winter Garden
Destination guide

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.

Things to do

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.


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.


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.

Natural features

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.

How to get there

Transportation to and around Winter Garden

The nearest airport is in Kissimmee, FL (ISM-Kissimmee Gateway), located 17.2 mi (27.7 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Orlando, FL (MCO-Orlando Intl.), which is 19.6 mi (31.6 km) away.

How many vacation rentals are available around Winter Garden?

Our 2021 property listings offer a large selection of 23,837 vacation rentals around Winter Garden. From 18,192 house rentals to 5,446 villa rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.