Hotels in Oakland

Photo by Gregg Yutko

Hotels.com makes it easy and rewarding. Always

Reward yourself your way

Stay where you want, when you want, and get rewarded

Learn about Hotels.com Rewards

Unlock instant savings

You could get an extra 10% off with Secret Prices

Sign up, it's free     Sign in

Free cancellation

Flexible bookings on most hotels*

Where to stay in Oakland?

Find out more about Oakland

What's Oakland Like?

If you're looking for the perfect part of the city to explore, why not consider Oakland? Places to visit like Bella Collina Golf Club and Oakland Nature Preserve are not far away. Garden Theatre and Winter Garden Art Association are two places to visit nearby.

Where are the Best Places to Stay in Oakland?

One of the top places to stay in Oakland:

The Oak View Place..

City-center apartment with patio
  • Outdoor pool • Garden

How to Get to Oakland

Oakland is located 2.9 mi (4.7 km) from the heart of Winter Garden.

Flying to:

  • Orlando Intl. Airport (MCO), 21.5 mi (34.6 km) from Oakland
  • Leesburg, FL (LEE-Leesburg Intl.), 21.4 mi (34.5 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 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)
  • Winter Garden Heritage Museum (3 mi/4.8 km away)

When Is the Best Time to Visit Winter Garden?

Keep exploring