Oakland Vacation Packages 2026 from $364

Photo by Gregg Yutko

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

$364

per person

Jan 11 - Jan 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.4/10 Very Good! (7,259 reviews)

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

$2,354

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

9.2/10 Wonderful! (1,001 reviews)

Westgate Palace Hotel / Universal / I-Drive

International Drive District

$466

per person

Jan 11 - Jan 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

9/10 Wonderful! (1,334 reviews)

Hotel was fantastic. The suite was clean and well kept, staff is quick to bring any requested extras like towels. Hot tub and arcade were a huge bonus and much needed. Didn’t use the pool or fire pit but it’s great that it has those amenities plus more. Only minor improvement could be parking but they do have an overflow parking location and a shuttle at least

Reviewed on Oct 21, 2026

Westgate Vacation Villas Resort

Save 100% on your flight

$381

per person

Jan 11 - Jan 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.2/10 Very Good! (2,082 reviews)

Westgate Towers Resort

Save 100% on your flight

$371

per person

Jan 11 - Jan 17

found 19 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.6/10 Excellent! (1,004 reviews)

Good save

Reviewed on Oct 23, 2026

Oakland Hotel Deals

Marriott's Grande Vista

5925 Avenida Vista Orlando FL

Fully refundableReserve now, pay when you stay

$96 nightly

$108 total

Nov 15 - Nov 16

Total with taxes and fees

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Fully refundableReserve now, pay when you stay

$111 nightly

$125 total

Nov 16 - Nov 17

Total with taxes and fees

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Fully refundable

$93 nightly

$104 total

Nov 16 - Nov 17

Total with taxes and fees

8.6/10 Excellent! (7,128 reviews)

"Let start with, I do not leave reviews often, and never negative until now. We were placed on the 18th floor, the elevators were always slow to arrive. The water pressure in shower was horrible, very light. The toilet could barely flush regardless if anything in it or not, and the overall condition ..."

Reviewed on Oct 23, 2026

See all 42,326 properties 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.