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Hotels in Oakland

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Where to stay in Oakland?

Universal's Cabana Bay Beach Resort
Relax by the pool surrounded by lush tropical plants and palm trees, with a soothing waterfall feature and vibrant tile accents.

Universal's Cabana Bay Beach Resort

3.5 star property
9.0 out of 10, Wonderful, (5085)
"Excellent stay"
Anonymous traveler
"Wonderful place to stay! Perfect to access Volcano Bay! "
Alison
$160 nightly
The price is $180
Aug 6 - Aug 7
Total includes taxes and fees
Universal's Cabana Bay Beach Resort
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.
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Our prices for Winter Garden are cheapest in September

See average prices and weather for all months
Price trends for hotels in Winter Garden
Pricing is based on two traveler single night rates
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Currently viewing crowd sizes and weather for August.
Weather forecast for Winter Garden
August
trending_upHigh crowds
High 90°F / low 77°F. Partly sunny.
View properties in August
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August, High crowds, average high temperature 90 degrees Fahrenheit, average low temperature 77 degrees Fahrenheit. Partly sunny.
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September, Moderate crowds, average high temperature 88 degrees Fahrenheit, average low temperature 75 degrees Fahrenheit. Partly sunny.
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October, Moderate crowds, average high temperature 83 degrees Fahrenheit, average low temperature 68 degrees Fahrenheit. Sunny most days.
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November, Low crowds, average high temperature 76 degrees Fahrenheit, average low temperature 61 degrees Fahrenheit. Sunny most days.
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December, Moderate crowds, average high temperature 73 degrees Fahrenheit, average low temperature 56 degrees Fahrenheit. Sunny most days.
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January, Low crowds, average high temperature 69 degrees Fahrenheit, average low temperature 52 degrees Fahrenheit. Sunny most days.
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February, Low crowds, average high temperature 73 degrees Fahrenheit, average low temperature 56 degrees Fahrenheit. Sunny most days.
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March, High crowds, average high temperature 78 degrees Fahrenheit, average low temperature 59 degrees Fahrenheit. Sunny most days.
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April, Moderate crowds, average high temperature 82 degrees Fahrenheit, average low temperature 64 degrees Fahrenheit. Sunny most days.
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May, Low crowds, average high temperature 87 degrees Fahrenheit, average low temperature 69 degrees Fahrenheit. Sunny most days.
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June, High crowds, average high temperature 89 degrees Fahrenheit, average low temperature 74 degrees Fahrenheit. Partly sunny.
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July, High crowds, average high temperature 90 degrees Fahrenheit, average low temperature 76 degrees Fahrenheit. Partly sunny.
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Monthly weather averages (˚F)

Top landmarks in Winter Garden

Flamingo Crossings Town Center

If you want to give your credit card some exercise, head out to Flamingo Crossings Town Center in Bay Lake.

See properties in Flamingo Crossings Town Center
Flamingo Crossings Town Center

Check out reviews of Oakland hotels guests love

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Good all."
Leomary 7-night trip
Posted 9 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Frequently asked questions

Is Oakland expensive to stay in?
You can find great hotels from $55 in Oakland to suit a range of budgets. To find the best low-cost hotel on Hotels.com that meets your needs, apply your search filters and then sort hotels by "Price: low to high".
How can I find discounted rates and deals for Oakland hotels?
Unlocking discounted rates at hotels in Oakland couldn't be simpler. Members save up to 20% on select hotels when signed in. Silver, Gold, and Platinum members can earn additional rewards on VIP Access bookings.
Can I receive a refund if I cancel my Oakland hotel booking?
The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel your booking. Some Oakland hotels require you to cancel more than 24 hours before check-in, so look at your booking beforehand. For extra peace of mind before you book, filter hotels by "Property cancellation options" and select "Fully refundable property".
What are some of the best pet-friendly hotels in Oakland?
Traveling with your pet doesn't mean sacrificing a great hotel stay. In Oakland, our travelers love:To find more pet-friendly stays on Hotels.com, use the "Amenities" filter in your search and select "Pet friendly".
What are some of the best Oakland hotels with a pool?
Book a Oakland hotel with a pool for some added relaxation or exercise on your trip. For more Oakland hotels with a pool, use the "Amenities" filter in your search and select "Pool" on Hotels.com.
Is it worth staying in Oakland?
There are 7 hotels in the area to find your perfect somewhere. Basing yourself in Oakland makes it easy to explore Winter Garden, including the neighborhoods of Downtown Winter Garden and Killarney.
What are some great hotels in Oakland with balconies?
There are some top hotels in Oakland that offer rooms with a balcony.
Are all taxes and fees included in the Oakland hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.

Find out more about 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? Take time to see the sights like Oakland Nature Preserve while you're here. Bella Collina Golf Club and West Orange Trail 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

Flying to:

  • Leesburg, FL (LEE-Leesburg Intl.), 21.4 mi (34.5 km) from Oakland
  • Orlando Intl. 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)
  • Plant Street Market (2.6 mi/4.3 km away)
  • Resurrection Catholic Church (2.9 mi/4.6 km away)
  • Newton Park (3.2 mi/5.1 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?