Photo by Gregg Yutko

Hotels in Oakland, Winter Garden

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January 2025

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Where to stay in Oakland?

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top landmarks in Winter Garden

Find out more about Oakland

What's Oakland like?

If you're in search of the perfect part of town to visit, why not consider Oakland? Take time to see the sights such as Oakland Nature Preserve while you're here. Bella Collina Golf Club and West Orange Trail are two places to visit nearby.

How to get to Oakland

Flying to:

  • Leesburg, FL (LEE-Leesburg Intl.), 21.4 mi (34.5 km) from Oakland
  • Orlando International Airport (MCO), 21.5 mi (34.6 km) from Oakland
  • Kissimmee, FL (ISM-Kissimmee Gateway), 21.6 mi (34.8 km) from Oakland

Things to see and do in and around Oakland

Things to see near Oakland:

  • Oakland Nature Preserve (0.6 mi/0.9 km away)
  • Hancock Park (5 mi/8 km away)
  • Resurrection Catholic Church (2.9 mi/4.6 km away)
  • Warrior Park (4.7 mi/7.6 km away)

Things to do near Oakland:

  • Bella Collina Golf Club (4.5 mi/7.2 km away)
  • Garden Theatre (2.9 mi/4.6 km away)
  • Winter Garden Art Association (2.9 mi/4.7 km away)
  • Central Florida Railroad Museum (2.9 mi/4.7 km away)
  • Carter Family Bowl (3 mi/4.8 km away)

When is the best time to visit Winter Garden?

  • Hottest months: August, July, June, September (average 28°C)
  • Coldest months: January, February, December, March (average 18°C)
  • Rainiest months: August, July, September, June (average 217 mm of rainfall)

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