Oakland Vacation Packages for 2025

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Top Hotel Deals

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
5.26 km from Oakland
Stay at this 4-star beach resort in Fort Walton Beach. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
Courtyard by Marriott Sandestin Grand Boulevard

Courtyard by Marriott Sandestin Grand Boulevard

3 out of 5
100 Grand Blvd, Miramar Beach, Miramar Beach, FL
30.59 km from Oakland
Stay at this 3-star business-friendly hotel in Miramar Beach. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Homewood Suites by Hilton Destin

Homewood Suites by Hilton Destin

3 out of 5
14051 Emerald Coast Parkway, Destin, FL
17.41 km from Oakland
Stay at this 3-star business-friendly hotel in Destin. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and ...
Home2 Suites By Hilton Destin

Home2 Suites By Hilton Destin

3 out of 5
14060 Emerald Coast Pkwy, Destin, FL
17.61 km from Oakland
Stay at this 3-star hotel in Destin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Wyndham Garden Fort Walton Beach Destin

Wyndham Garden Fort Walton Beach Destin

3 out of 5
573 Santa Rosa Blvd, Fort Walton Beach, FL
3.19 km from Oakland
Stay at this 3-star 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 ...
Spark by Hilton Destin

Spark by Hilton Destin

3 out of 5
4415 Commons Dr E, Destin, FL
20.01 km from Oakland
Stay at this 3-star 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
Stay at this 5-star 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 ...
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
Stay at this 3-star business-friendly hotel in Miramar Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
SummerPlace Inn Destin

SummerPlace Inn Destin

3 out of 5
14047 Emerald Coast Pkwy, Destin, FL
17.37 km from Oakland
Stay at this 3-star business-friendly hotel in Destin. Enjoy free WiFi, free parking, and a 24-hour fitness center. 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
Stay at this 4-star 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 ...
Residence Inn by Marriott Sandestin at Grand Boulevard

Residence Inn by Marriott Sandestin at Grand Boulevard

3 out of 5
300 Grand Blvd, Miramar Beach, Miramar Beach, FL
30.87 km from Oakland
Stay at this 3-star hotel in Miramar Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Days Inn by Wyndham Destin

Days Inn by Wyndham Destin

2.5 out of 5
1029 Highway 98 East, Hwy 98 And Airport Road, Destin, FL
16.42 km from Oakland
Book a stay at this business-friendly hotel in Destin. Enjoy free parking, a 24-hour front desk, and a business center. Our guests praise the helpful staff and ...
Club Destin Condos

Club Destin Condos

2.5 out of 5
1085 US-98, Destin, FL
16.84 km from Oakland
Stay at this apartment in Destin. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular ...
Motel 6 Destin, FL

Motel 6 Destin, FL

2 out of 5
405 Highway 98 East #A, Destin, FL
13.31 km from Oakland
Stay at this motel in Destin. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
SpringHill Suites by Marriott Navarre Beach

SpringHill Suites by Marriott Navarre Beach

4 out of 5
8375 Gulf Blvd, Navarre, FL
23.01 km from Oakland
Stay at this 4-star beach hotel in Navarre. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the restaurant in our reviews. ...
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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
Mon, Feb 9 - Thu, Feb 19
MSP
Minneapolis - St. Paul Intl.
VPS
Northwest Florida Regional
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Feb 9 from Minneapolis - St. Paul Intl. to Northwest Florida Regional, returning Thu, Feb 19, priced at $218 found 1 day ago
Delta
Tue, Feb 10 - Thu, Feb 19
MSP
Minneapolis - St. Paul Intl.
VPS
Northwest Florida Regional
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Feb 10 from Minneapolis - St. Paul Intl. to Northwest Florida Regional, returning Thu, Feb 19, priced at $257 found 1 day ago
American Airlines
Mon, Feb 9 - Wed, Feb 18
MSP
Minneapolis - St. Paul Intl.
VPS
Northwest Florida Regional
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Feb 9 from Minneapolis - St. Paul Intl. to Northwest Florida Regional, returning Wed, Feb 18, priced at $277 found 1 day ago
Sun Country Airlines
Thu, Feb 12 - Mon, Feb 16
MSP
Minneapolis - St. Paul Intl.
VPS
Northwest Florida Regional
$436 Roundtrip, found 1 day ago
$436
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Thu, Feb 12 from Minneapolis - St. Paul Intl. to Northwest Florida Regional, returning Mon, Feb 16, priced at $436 found 1 day ago