Oakland Vacations from $697
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The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Bay Club of Sandestin
Price was $950, price is now $697 per person
$697
per person
Dec 26 - Dec 31
found 13 hours ago
Roundtrip flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
9/10 Wonderful! (153 reviews)
It was a beautiful place to stay and the staff were so friendly and helpful.
Reviewed on Jul 3, 2025
The Henderson Beach Resort & Spa
Crystal Beach
Price was $1,864, price is now $1,329 per person
$1,329
per person
Nov 23 - Nov 30
found 5 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,005 reviews)
Incredibly memorable 60th birthday destination.
Beautiful place, really top-notch. Great welcoming staff, friendly people throughout. It was like we ride to White Lotus, without all the other drama! I highly recommend.
Reviewed on Oct 7, 2025
Sun by Avantstay Gulf Place Golf Cart, Pool, Bikes
Save 100% on your flight
Price was $1,858, price is now $1,405 per person
$1,405
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
10/10 Exceptional! (2 reviews)
The property was clean and well maintained definitely would stay here again!
Reviewed on Aug 24, 2025
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
Fairfield Inn & Suites by Marriott Fort Walton Beach Hurlburt Area
522 Mary Esther Cutoff NW, Fort Walton Beach, FL
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $85 total per night from Nov 2 to Nov 3
$85 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (495 reviews)
"it provided everything i needed. thank you"
Reviewed on Oct 1, 2025
The Island Resort at Fort Walton Beach
Miracle Strip Parkway Southeast, 1500, Fort Walton Beach, FL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $148 total per night from Oct 26 to Oct 27
$148 total
Oct 26 - Oct 27
Total with taxes and fees
8.2/10 Very Good! (2,879 reviews)
"A great hotel on the Gulf with the most amazing sand. What an amazing find"
Reviewed on Oct 10, 2025
Courtyard by Marriott Sandestin Grand Boulevard
100 Grand Blvd, Miramar Beach, Miramar Beach, FL
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $85 total per night from Oct 27 to Oct 28
$85 total
Oct 27 - Oct 28
Total with taxes and fees
9/10 Wonderful! (1,449 reviews)
"Everything is amazing"
Reviewed on Oct 10, 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
Okaloosa Island Beach
4.5/5(26 reviews)
Why not spend a lazy afternoon at Okaloosa Island Beach during your trip to Fort Walton Beach? Wander the beautiful beaches and seaside in this relaxing area.
Okaloosa Island Pier
4.5/5(118 reviews)
Find out about the history of Fort Walton Beach when you take a trip to Okaloosa Island Pier. Stroll along the seaside in this family-friendly area, or check out its seafood restaurants.
Wild Willy's Adventure Zone
4/5(55 reviews)
Enjoy fun for the whole family at an entertainment center that offers everything from ropes courses to roller coasters and mini golf.
Things to do
Destin Harbor Sunset Eco Dolphin Cruise
$35
per adult
80% of travellers recommend
Jetski Waverunner Rental - Destin
$95
per traveler
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.