Oakland Vacations from $254
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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.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
Price was $561, price is now $254 per person
$254
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,346 reviews)
I didn’t like about their room service and staff
Reviewed on Oct 9, 2025
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was $776, price is now $315 per person
$315
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (1,012 reviews)
Very child friendly. The staff was fine and it is very convenient to get to Universal!
Reviewed on Oct 9, 2025
Westgate Town Center Resort
Save 100% on your flight
Price was $522, price is now $254 per person
$254
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,360 reviews)
Over All It Was Great Me And My Kids Had Wonderful Time And Wanna Go Back
Reviewed on Oct 1, 2025
The Delaney Hotel
South Orange
Price was $651, price is now $327 per person
$327
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.6/10 Exceptional! (1,003 reviews)
The only complaint I have is that the walls are very thin. I could here the man in the next room sneeze continuously. There was also a lot of noise from people in hallway, and doors slamming.
Reviewed on Oct 9, 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 refundable
$81 nightly
The price is $91 total per night from Nov 2 to Nov 3
$91 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (6,736 reviews)
"Yes"
Reviewed on Oct 8, 2025
Universal's Cabana Bay Beach Resort
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $156 total per night from Nov 5 to Nov 6
$156 total
Nov 5 - Nov 6
Total with taxes and fees
8.8/10 Excellent! (5,365 reviews)
"Rooms need to be cleaned better."
Reviewed on Oct 9, 2025
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr, Orlando, FL
$91 nightly
The price is $103 total per night from Nov 3 to Nov 4
$103 total
Nov 3 - Nov 4
Total with taxes and fees
9.2/10 Wonderful! (3,633 reviews)
"Nice area, lots to do, very cost effective compared to other resorts in area"
Reviewed on Oct 6, 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 family-friendly 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
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$32
per adult
90% of travellers recommend
Universal Orlando Resort Express Passes
$160
per traveler
84% of travellers recommend
Explore a world of travel with Expedia
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- Car rental Orlando Airport (MCO)
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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.