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Oak Vacation Packages

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Oak Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
OYO Hotel Pensacola I-10 & Hwy 29

OYO Hotel Pensacola I-10 & Hwy 29

2 out of 5
Price was $885, price is now $659 per person
$659
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Pensacola (PNS)
Stay at this hotel in Pensacola. Enjoy free WiFi, free parking, and room service. Popular attractions Splash City Adventures and Marcus Pointe Golf Club are located nearby.
Portofino Island Resort

Portofino Island Resort

4 out of 5
Save 100% on your flight
Price was $3,024, price is now $1,877 per person
$1,877
per person
Jun 24 - Jun 30
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Book a stay at this beach aparthotel in Pensacola Beach. Enjoy free WiFi, free parking, and 8 outdoor pools. Our guests praise the property condition in our reviews. Popular attractions Pensacola Beach Boardwalk and Park East On-Leash Dog Beach are located nearby.
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,857, price is now $1,335 per person
$1,335
per person
May 16 - May 23
found 23 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)
Book a stay at this beach hotel in Pensacola Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Pensacola Beach Boardwalk and Casino Beach are located nearby.
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,526, price is now $1,826 per person
$1,826
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Stay at this hotel in Pensacola. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Seville Square and Bartram Park are located nearby.
Landing Apartments Pensacola - Belleview Heights

Landing Apartments Pensacola - Belleview Heights

4 out of 5
Save 100% on your flight
Price was $1,019, price is now $745 per person
$745
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Pensacola (PNS)
Stay at this apartment in Pensacola. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Marcus Pointe Golf Club and Osceola Municipal Golf Course are located nearby.
Beach Club Resort Residence and Spa

Beach Club Resort Residence and Spa

4.5 out of 5
Save 100% on your flight
Price was $1,765, price is now $1,303 per person
$1,303
per person
Jun 6 - Jun 11
found 10 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Pensacola (PNS)
Book a stay at this luxury aparthotel in Pensacola Beach. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Pensacola Beach Boardwalk and Casino Beach are located nearby.
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Price was $1,496, price is now $1,118 per person
$1,118
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)
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 reviews. Popular attractions Destin Beaches and Okaloosa Island Beach are located nearby.
The Lodge at Gulf State Park, A Hilton Hotel

The Lodge at Gulf State Park, A Hilton Hotel

4 out of 5
Price was $975, price is now $745 per person
$745
per person
May 23 - May 25
found 10 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)
Book a stay at this beach resort in Orange Beach. Enjoy free WiFi, 5 restaurants, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Gulf Shores Beach and Gulf State Park are located nearby.

Oak Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Beachside Resort Hotel

Beachside Resort Hotel

2 out of 5
Price was $882, price is now $645 per person
$645
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
The Lodge at Gulf State Park, A Hilton Hotel

The Lodge at Gulf State Park, A Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $1,213, price is now $890 per person
$890
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Portofino Island Resort

Portofino Island Resort

4 out of 5
Save 100% on your flight
Price was $1,446, price is now $1,073 per person
$1,073
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Okaloosa Island
Price was $1,496, price is now $1,118 per person
$1,118
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)

Oak Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Landing Apartments Pensacola - Belleview Heights

Landing Apartments Pensacola - Belleview Heights

4 out of 5
Save 100% on your flight
Price was $1,019, price is now $745 per person
$745
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Pensacola (PNS)
Portofino Island Resort

Portofino Island Resort

4 out of 5
Save 100% on your flight
Price was $3,024, price is now $1,877 per person
$1,877
per person
Jun 24 - Jun 30
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Villa Sabine
Save 100% on your flight
Price was $1,857, price is now $1,335 per person
$1,335
per person
May 16 - May 23
found 23 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Downtown Pensacola
Save 100% on your flight
Price was $2,526, price is now $1,826 per person
$1,826
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Fri, May 1 - Tue, May 19
ATL
Hartsfield-Jackson Atlanta Intl.
PNS
Pensacola Intl.
$131 Roundtrip, found 4 days ago
$131
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, May 1 from Hartsfield-Jackson Atlanta Intl. to Pensacola Intl., returning Tue, May 19, priced at $131 found 4 days ago
Frontier Airlines
Sat, May 2 - Sat, May 9
DFW
Dallas-Fort Worth Intl.
PNS
Pensacola Intl.
$160 Roundtrip, found 1 hour ago
$160
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, May 2 from Dallas-Fort Worth Intl. to Pensacola Intl., returning Sat, May 9, priced at $160 found 1 hour ago
Spirit Airlines
Wed, May 13 - Wed, May 20
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$171 Roundtrip, found 9 hours ago
$171
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Wed, May 13 from O'Hare Intl. to Pensacola Intl., returning Wed, May 20, priced at $171 found 9 hours ago
Frontier Airlines
Tue, May 5 - Tue, May 5
MIA
Miami Intl.
PNS
Pensacola Intl.
$186 Roundtrip, found 2 days ago
$186
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, May 5 from Miami Intl. to Pensacola Intl., returning Tue, May 5, priced at $186 found 2 days ago