Oakland Vacations from $160
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Your Oakland Vacation
Experience all the wonderful things this neighborhood has to offer with a tailor-made Oakland vacation package. However you see yourself spending your time here, you'll find countless opportunities for fun, adventure and relaxation. When it's time to get out and explore, you'll find a lot of big-name attractions nearby including West Orange Trail, Resurrection Catholic Church and Oakland Nature Preserve. Visit one or all during your trip to Oakland. No matter what your ideal Oakland vacation looks like, you can make it a reality with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
Price was $475, price is now $160 per person
$160
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,171 reviews)
Gould be a good idea to provided some info how to open the gate
Reviewed on Aug 24, 2025
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
Price was $580, price is now $266 per person
$266
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,254 reviews)
We were checked in by the supervisor named Jamal. He did an excellent job and made us feel at home. He was the best.
Reviewed on Aug 24, 2025
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was $792, price is now $372 per person
$372
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (1,002 reviews)
This was a good time!
Reviewed on Aug 23, 2025
Westgate Cocoa Beach Resort
Price was $1,297, price is now $616 per person
$616
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
8.8/10 Excellent! (481 reviews)
It was a okay stay. Not enough washer and dryers for the whole resort - literally people were hovering over me watching me while trying to dry my clothes after the beach/pool. Rooms are okay. Jacuzzi and pool was nice. Relaxing for the most part, I did like how often we saw security. Not much offered to do besides the pool. Thought there would be more for a resort.
Reviewed on Aug 24, 2025
Westgate Blue Tree Resort in Lake Buena Vista
Save 100% on your flight
Price was $815, price is now $411 per person
$411
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.4/10 Very Good! (1,001 reviews)
There was a very shady old looking red car parked outside our windows with loud music playing late into the night our last two nights
Reviewed on Aug 19, 2025
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Vista del Lago
While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.
Oakland Hotel Deals
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Sep 10 to Sep 11
$104 total
Sep 10 - Sep 11
Total with taxes and fees
8.2/10 Very Good! (6,552 reviews)
"."
Reviewed on Aug 23, 2025
Marriott's Grande Vista
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $98 total per night from Sep 15 to Sep 16
$98 total
Sep 15 - Sep 16
Total with taxes and fees
8.8/10 Excellent! (2,925 reviews)
"Excellent place great customer service and Beautiful room clean, spacious, overall excellent quality love the pool. Would recommend it also definitely going again.."
Reviewed on Aug 24, 2025
Rosen Inn at Pointe Orlando
9000 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $68 total per night from Aug 27 to Aug 28
$68 total
Aug 27 - Aug 28
Total with taxes and fees
8.4/10 Very Good! (4,815 reviews)
"I loved staying at this property. We stayed for a weekend while we visited Orlando. The room was clean, and the view was spectacular from the top floor. Loved the pool, will visit again!"
Reviewed on Aug 24, 2025
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.
Discover the most popular places to visit in Oakland
Flamingo Crossings Town Center
You can do some window-shopping at Flamingo Crossings Town Center during your visit to Winter Garden. Discover the top-notch restaurants and entertainment choices in this walkable area.
Orange County National Golf Club
Enjoy a round of golf in Winter Garden at Orange County National Golf Club. Amble around this family-friendly area's lakeside or experience its entertainment choices.
Disney's Palm Golf Course
Enjoy a round of golf in Winter Garden at Disney's Palm Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
Things to do
Universal Orlando Resort Express Passes
$149
per traveler
84% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
90% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Orlando Hotels
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- Hotels near Oakland Nature Preserve
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- Universal Orlando Resort in Winter Garden
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- Car rental Orlando Airport (MCO)
- Car rentals near Orlando
- Car rentals near Winter Garden
- Enterprise Rental Cars in Winter Garden
- Car rentals near Resurrection Catholic Church
- Car rentals near Winter Garden Art Association
- Budget Rental Cars in Winter Garden
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.