Oakland Vacation Packages for 2026

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Top Hotel Deals

Fairfield Inn & Suites by Marriott Fort Walton Beach Hurlburt Area

Fairfield Inn & Suites by Marriott Fort Walton Beach Hurlburt Area

3 out of 5
522 Mary Esther Cutoff NW Fort Walton Beach FL
1.32 km from Oakland
Stay at this hotel in Fort Walton Beach. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Okaloosa Island Beach and Boardwalk on Okaloosa ...
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Miracle Strip Parkway Southeast, 1500 Fort Walton Beach FL
5.32 km from Oakland
Book a stay at this beach resort in Fort Walton Beach. Enjoy free WiFi, 2 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool in our ...
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
9300 Emerald Coast Pkwy W Miramar Beach FL
29.77 km from Oakland
Book a stay at this beach aparthotel in Miramar Beach. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the helpful staff in our reviews. ...
Hyatt House Destin

Hyatt House Destin

3 out of 5
4415 Legendary Dr Destin FL
21.31 km from Oakland
Book a stay at this business-friendly hotel in Destin. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Big Kahuna's Water and Adventure ...
Wyndham Garden Fort Walton Beach Destin

Wyndham Garden Fort Walton Beach Destin

3 out of 5
573 Santa Rosa Blvd Fort Walton Beach FL
3.21 km from Oakland
Book a stay at this beach hotel in Fort Walton Beach. Enjoy free WiFi, 2 outdoor pools, and a beach locale. Our guests praise the pool and the helpful staff ...
Village Inn Destin

Village Inn Destin

2 out of 5
215 Harbor Blvd Destin FL
12.81 km from Oakland
Book a stay at this business-friendly motel in Destin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Hilton Garden Inn Destin Miramar Beach

Hilton Garden Inn Destin Miramar Beach

3 out of 5
220 Scenic Gulf Drive Miramar Beach FL
27.72 km from Oakland
Book a stay at this business-friendly hotel in Miramar Beach. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff ...
Spark by Hilton Destin

Spark by Hilton Destin

3 out of 5
4415 Commons Dr E Destin FL
20.01 km from Oakland
Book a stay at this business-friendly hotel in Destin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
200 Henderson Resort Way Destin FL
20.07 km from Oakland
Book a stay at this luxury resort in Destin. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
WoodSpring Suites Fort Walton Beach - Eglin AFB

WoodSpring Suites Fort Walton Beach - Eglin AFB

2.5 out of 5
765 MARTIN LUTHER KING JR BLVD Fort Walton Beach FL
3.3 km from Oakland
Stay at this hotel in Fort Walton Beach. Enjoy free parking, a 24-hour fitness center, and a 24-hour front desk. Popular attractions Okaloosa Island Beach and ...
La Quinta Inn & Suites by Wyndham Miramar Beach-Destin

La Quinta Inn & Suites by Wyndham Miramar Beach-Destin

3 out of 5
12839 Emerald Coast Pkwy Miramar Beach FL
24.41 km from Oakland
Book a stay at this business-friendly hotel in Miramar Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hotel Effie Sandestin, Autograph Collection

Hotel Effie Sandestin, Autograph Collection

4 out of 5
1 Grand Sandestin Boulevard Miramar Beach FL
30.14 km from Oakland
Book a stay at this luxury hotel in Miramar Beach. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the helpful staff in our ...
Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
540 Santa Rosa Blvd Fort Walton Beach FL
3.05 km from Oakland
Book a stay at this beach hotel in Fort Walton Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff ...
Destin Inn and Suites

Destin Inn and Suites

2 out of 5
713 Harbor Blvd.( highway 98 east) Destin FL
14.96 km from Oakland
Book a stay at this business-friendly motel in Destin. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
Sundrift Inn

Sundrift Inn

3 out of 5
414 Santa Rosa Boulevard Fort Walton Beach FL
3.66 km from Oakland
Book a stay at this beach hotel in Fort Walton Beach. Enjoy free WiFi, a beach locale, and a fitness center. Popular attractions Destin Harbor Boardwalk and ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Oct 6 - Wed, Oct 28
ATL
Hartsfield-Jackson Atlanta Intl.
VPS
Northwest Florida Regional
$198 Roundtrip, found 5 days ago
$198
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Oct 6 from Hartsfield-Jackson Atlanta Intl. to Northwest Florida Regional, returning Wed, Oct 28, priced at $198 found 5 days ago
Delta
Tue, Oct 20 - Wed, Nov 11
MSP
Minneapolis - St. Paul Intl.
VPS
Northwest Florida Regional
$198 Roundtrip, found 4 days ago
$198
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Oct 20 from Minneapolis - St. Paul Intl. to Northwest Florida Regional, returning Wed, Nov 11, priced at $198 found 4 days ago
Southwest Airlines
Tue, Oct 6 - Wed, Oct 28
ATL
Hartsfield-Jackson Atlanta Intl.
VPS
Northwest Florida Regional
$217 Roundtrip, found 5 days ago
$217
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Oct 6 from Hartsfield-Jackson Atlanta Intl. to Northwest Florida Regional, returning Wed, Oct 28, priced at $217 found 5 days ago
American Airlines
Tue, Oct 6 - Wed, Oct 28
ATL
Hartsfield-Jackson Atlanta Intl.
VPS
Northwest Florida Regional
$227 Roundtrip, found 5 days ago
$227
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Oct 6 from Hartsfield-Jackson Atlanta Intl. to Northwest Florida Regional, returning Wed, Oct 28, priced at $227 found 5 days ago