Oakland Vacation Packages for 2026

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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
5.32 km from Oakland
Book a stay at this 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 FL
30.59 km from Oakland
Book a stay at this business-friendly hotel in Miramar Beach. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hilton Sandestin Beach Golf Resort & Spa

Hilton Sandestin Beach Golf Resort & Spa

4 out of 5
4000 S Sandestin Blvd Miramar Beach FL
30.22 km from Oakland
Book a stay at this beach resort in Miramar Beach. Enjoy 2 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the ...
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 ...
Days Inn by Wyndham Destin

Days Inn by Wyndham Destin

2.5 out of 5
1029 Highway 98 East 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 daily housekeeping. Our guests praise the helpful staff ...
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 ...
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. ...
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 ...
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 ...
Club Destin Condos

Club Destin Condos

2.5 out of 5
1085 US-98 Destin FL
16.82 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 ...
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 ...
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
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 ...
SummerPlace Inn Destin

SummerPlace Inn Destin

3 out of 5
14047 Emerald Coast Pkwy Destin FL
17.37 km from Oakland
Book a stay at this business-friendly hotel in Destin. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
Comfort Inn & Suites Destin near Henderson Beach

Comfort Inn & Suites Destin near Henderson Beach

2.5 out of 5
4401 COMMONS DRIVE EAST Destin FL
19.86 km from Oakland
Book a stay at this business-friendly hotel in Destin. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff 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 hotel in Destin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
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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
$258 Roundtrip, found 15 hours ago
$258
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, Oct 6 from Hartsfield-Jackson Atlanta Intl. to Northwest Florida Regional, returning Wed, Oct 28, priced at $258 found 15 hours ago
American Airlines
Wed, Jun 3 - Sat, Jun 6
DFW
Dallas-Fort Worth Intl.
VPS
Northwest Florida Regional
$276 Roundtrip, found 15 hours ago
$276
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Wed, Jun 3 from Dallas-Fort Worth Intl. to Northwest Florida Regional, returning Sat, Jun 6, priced at $276 found 15 hours ago
Southwest Airlines
Tue, Jul 21 - Fri, Jul 24
ATL
Hartsfield-Jackson Atlanta Intl.
VPS
Northwest Florida Regional
$277 Roundtrip, found 11 hours ago
$277
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Tue, Jul 21 from Hartsfield-Jackson Atlanta Intl. to Northwest Florida Regional, returning Fri, Jul 24, priced at $277 found 11 hours ago
JetBlue Airways
Fri, May 29 - Thu, Jun 4
PHL
Philadelphia Intl.
VPS
Northwest Florida Regional
$374 Roundtrip, found 5 days ago
$374
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, May 29 from Philadelphia Intl. to Northwest Florida Regional, returning Thu, Jun 4, priced at $374 found 5 days ago
Sun Country Airlines
Sat, Oct 10 - Fri, Oct 16
MSP
Minneapolis - St. Paul Intl.
VPS
Northwest Florida Regional
$406 Roundtrip, found 5 days ago
$406
Roundtrip
found 5 days ago
Select Sun Country Airlines flight, departing Sat, Oct 10 from Minneapolis - St. Paul Intl. to Northwest Florida Regional, returning Fri, Oct 16, priced at $406 found 5 days ago