Oakland Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Oakland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
SummerPlace Inn Destin
Price was $710, price is now $597 per person
$597
per person
Aug 21 - Aug 25
found 14 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Fort Walton Beach (VPS)
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 staff in our reviews. Popular attractions Big Kahuna's Water and Adventure Park and Destin Beaches are located nearby.
Sandestin Golf and Beach Resort
Price was $946, price is now $686 per person
$686
per person
Aug 21 - Aug 25
found 14 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Fort Walton Beach (VPS)
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. Popular attractions Miramar Beach and Sandestin Golf Resort - Raven, Burnt Pine, Baytowne, The Links are located nearby.
The Henderson Beach Resort & Spa
Crystal Beach
Price was $1,233, price is now $961 per person
$961
per person
Aug 21 - Aug 25
found 14 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Fort Walton Beach (VPS)
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 reviews. Popular attractions Big Kahuna's Water and Adventure Park and Miramar Beach are located nearby.
Homewood Suites by Hilton Destin
Price was $830, price is now $663 per person
$663
per person
Aug 21 - Aug 25
found 14 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Fort Walton Beach (VPS)
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 in our reviews. Popular attractions Big Kahuna's Water and Adventure Park and Destin Beaches are located nearby.
Bay Club of Sandestin
Price was $750, price is now $601 per person
$601
per person
Aug 21 - Aug 25
found 14 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Fort Walton Beach (VPS)
Stay at this aparthotel in Miramar Beach. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Miramar Beach and Sandestin Golf Resort - Raven, Burnt Pine, Baytowne, The Links are located nearby.
Hyatt Place Sandestin at Grand Boulevard
Price was $720, price is now $621 per person
$621
per person
Aug 21 - Aug 25
found 14 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Fort Walton Beach (VPS)
Stay at this hotel in Miramar Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Miramar Beach and Grand Boulevard at Sandestin are located nearby.
Top Hotel Deals
Sandestin Golf and Beach Resort
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. ...
The Island Resort at Fort Walton Beach
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 ...
Days Inn by Wyndham Destin
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 ...
Wyndham Garden Fort Walton Beach Destin
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 ...
Courtyard by Marriott Sandestin at Grand Boulevard
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 ...
Comfort Inn Miramar Beach-Destin
12282 EMERALD COAST PKWY W Miramar Beach FL
25.24 km from Oakland
Stay at this hotel in Miramar Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hotel Effie Sandestin, Autograph Collection
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 ...
Hilton Garden Inn Destin Miramar Beach
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 ...
The Henderson Beach Resort & Spa
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 ...
Spark by Hilton Destin
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 ...
Comfort Inn & Suites Destin near Henderson Beach
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 ...
Village Inn Destin
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 ...
Hampton Inn & Suites Destin
1625 Scenic Highway 98 East Destin FL
17.37 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 ...
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.
Thu, Jul 9 - Fri, Jul 17
BOS
Logan Intl.
VPS
Northwest Florida Regional
$165 Roundtrip, found 13 hours ago
$165
Roundtrip
found 13 hours ago
Thu, Jul 9 - Fri, Jul 17
BOS
Logan Intl.
VPS
Northwest Florida Regional
$190 Roundtrip, found 13 hours ago
$190
Roundtrip
found 13 hours ago
Thu, Jul 9 - Fri, Jul 17
BOS
Logan Intl.
VPS
Northwest Florida Regional
$206 Roundtrip, found 13 hours ago
$206
Roundtrip
found 13 hours ago
Mon, Feb 1 - Mon, Mar 1
MSP
Minneapolis - St. Paul Intl.
VPS
Northwest Florida Regional
$246 Roundtrip, found 5 days ago
$246
Roundtrip
found 5 days ago
Tue, Jul 14 - Tue, Jul 28
DAL
Love Field
VPS
Northwest Florida Regional
$262 Roundtrip, found 2 days ago
$262
Roundtrip
found 2 days ago