Oakland Vacation Packages
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Top Holiday Package Deals in Oakland
Price found within the past 48 hours. Click for updated prices.
WaterSound Inn
WaterSound Beach
Price was CA $2,356, price is now CA $1,704 per person
CA $1,704
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Walton Beach (VPS)
9.4/10 Exceptional! (100 reviews)
The Manager and staff were very helpful and focused on providing us with a great experience. The hotel is very comfortable and the Beach Club is great!
Reviewed on Feb 21, 2026
Sandestin Golf and Beach Resort
Price was CA $2,495, price is now CA $1,724 per person
CA $1,724
per person
Jul 2 - Jul 6
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Walton Beach (VPS)
7.8/10 Good! (3,858 reviews)
Room was not clean nor ready when i got there. I also did not get a waterfront view. The property is huge with little directions on how to get anywhere. I also didnt feel welcomed. I would suggest peoplw
Reviewed on Apr 13, 2026
Hampton Inn & Suites Destin
Price was CA $2,432, price is now CA $1,890 per person
CA $1,890
per person
Jul 2 - Jul 6
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Walton Beach (VPS)
8.6/10 Excellent! (1,001 reviews)
The renovated room was nice and efficient, pool was well kept, breakfast has lots of varieties to choose from. Very walkable to public beach access. Staff is very helpful. They said they're almost done with renovating all the rooms.
Reviewed on Apr 25, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Okaloosa Island
5 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 $193 per night from May 4 to May 5
CA $193
CA $267 total
May 4 - May 5
includes taxes & fees
8.2/10 Very Good! (3,070 reviews)
We had an excellent stay! We loved having a water view when we woke up. The beach was maintained and gorgeous! My little kids had never been to the beach and this stay was perfect for their first experience! Wonderful memories were made!
Reviewed on Apr 27, 2026
Courtyard by Marriott Sandestin Grand Boulevard
100 Grand Blvd Miramar Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 11 to May 12
CA $167
CA $187 total
May 11 - May 12
includes taxes & fees
9.2/10 Wonderful! (1,640 reviews)
Everything was great, the only issue was the hot water wasn’t so hot.
Reviewed on Apr 27, 2026
Hilton Sandestin Beach Golf Resort & Spa
4000 S Sandestin Blvd Miramar Beach FL
The price is CA $471 per night from May 11 to May 12
CA $471
CA $589 total
May 11 - May 12
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
Clean room, great customer service, great location
Reviewed on Apr 27, 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.
Discover the most popular places to visit in Oakland
Okaloosa Island Pier
Okaloosa Island Pier is just one of the places to see in Fort Walton Beach, so why not enjoy the other things to explore during your travels? Wander the beautiful beaches and seaside in this family-friendly area.
Wild Willy's Adventure Zone
You can take time to visit Wild Willy's Adventure Zone during your travels to Fort Walton Beach. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Emerald Coast Science Center
You can spend time studying the exhibits at Emerald Coast Science Center during your travels in Fort Walton Beach. Wander the beautiful beaches and seaside in this family-friendly area.
Things to do
4 Hour Destin Harbor Crab Island Excursion
CA $103
per adult
100% of travellers recommend
Destin: Buccaneer Pirate Cruise
CA $76
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.