Oakland Vacation Packages
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Top Holiday Package Deals in Oakland
Price found within the past 48 hours. Click for updated prices.
Homewood Suites by Hilton Destin
Price was CA $1,333, price is now CA $1,111 per person
CA $1,111
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Walton Beach (VPS)
9/10 Wonderful! (1,441 reviews)
I love the pool with a grill available. And the room is really neat with the kitchenette
Reviewed on Jun 13, 2026
Spyglass by Avantstay 5BR + 3 Balconies + Community Pool Walk to Beach + Minutes to Harborwalk Village & Henderson Beach State Park
Price was CA $5,689, price is now CA $4,296 per person
CA $4,296
per person
Aug 2 - Aug 8
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Walton Beach (VPS)
No reviews
Sandestin Golf and Beach Resort
Price was CA $1,486, price is now CA $1,138 per person
CA $1,138
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Walton Beach (VPS)
7.8/10 Good! (3,909 reviews)
I was pretty disappointed with this place. The cleanliness was terrible for the price that you’re paying. The room smelled musty, there was trash under the bathroom counter, the pool had multiple, used band aids around it. Nothing was accessible unless you use the tram. Considering that they specifically charge you resort and cleaning fees ON TOP of what you’re already paying, basic cleanliness wasn’t too much to ask for.
Reviewed on Jun 11, 2026
The Henderson Beach Resort & Spa
Crystal Beach
Price was CA $1,922, price is now CA $1,536 per person
CA $1,536
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,007 reviews)
The only real major complaint we had was the children / teenagers at the "Adults Only" pool. There was no enforcement by hotel staff and when this was a deciding factor for choosing this resort, it was very annoying. The beach access from the main hotel is quite a hike (across the resort, across the road, and then down the boardwalk to the beach. Food was excellent at the hotel restaurants. Alcohol was very over priced! But all in all it is a nice getaway. If you have a passport, do an all inclusive resort in the Caribbean where you aren't paying $18 per mixed drink.
Reviewed on Jun 11, 2026
The Beach Grove by Avantstay Gulf-front Condo Direct Beach Access Shared Pool + Hot Tub + Fitness Center Miramar Beach
Price was CA $2,113, price is now CA $1,733 per person
CA $1,733
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Walton Beach (VPS)
No reviews
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Okaloosa Island
6 out of top 10 points of interest in this area
The perfect place for a romantic getaway or a family weekend retreat, this is an unforgettable shoreline delight.
Oakland Hotel Deals
The Island Resort at Fort Walton Beach
Miracle Strip Parkway Southeast, 1500 Fort Walton Beach FL
The price is CA $325 per night from Jun 29 to Jun 30
CA $325
CA $421 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (3,271 reviews)
"Loved and would go back over and over again. Awesome location and family friendly. I think their rooms can be updated some for the price and the bathrooms are TINY! Still worth the money if you want to have an awesome family vacation!"
Reviewed on Jun 14, 2026
Sandestin Golf and Beach Resort
9300 Emerald Coast Pkwy W Miramar Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $238 per night from Jun 22 to Jun 23
CA $238
CA $466 total
Jun 22 - Jun 23
includes taxes & fees
Wyndham Garden Fort Walton Beach Destin
573 Santa Rosa Blvd Fort Walton Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $332 per night from Jun 21 to Jun 22
CA $332
CA $375 total
Jun 21 - Jun 22
includes taxes & fees
8.2/10 Very Good! (2,380 reviews)
"Loved the view can't say enough, close to beach, our room was clean and spacious. Staff was friendly and the pool with the hot tub was clean and enjoyable"
Reviewed on Jun 14, 2026
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.
Stay near popular Oakland attractions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.