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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.
Beachside Resort Hotel

Beachside Resort Hotel

2 out of 5
Price was $973, price is now $717 per person
$717
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)
Stay at this hotel in Gulf Shores. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Gulf Shores Beach and Gulf State Park 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
Save 100% on your flight
Price was $1,774, price is now $1,251 per person
$1,251
per person
Mar 23 - Mar 30
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)
Book a stay at this beach resort in Gulf Shores. 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.
Beach Club Resort Residence and Spa

Beach Club Resort Residence and Spa

4.5 out of 5
Save 100% on your flight
Price was $1,672, price is now $1,192 per person
$1,192
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Pensacola Beach Gulf Pier are located nearby.
Embassy Suites By Hilton Gulf Shores Beach Resort

Embassy Suites By Hilton Gulf Shores Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,391, price is now $1,020 per person
$1,020
per person
Mar 23 - Mar 30
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)
Stay at this resort in Gulf Shores. Enjoy free breakfast, 3 restaurants, and 3 bars/lounges. Popular attractions Gulf Shores Beach and Gulf State Park are located nearby.
Emerald Isle

Emerald Isle

3 out of 5
Save 100% on your flight
Price was $1,921, price is now $1,415 per person
$1,415
per person
Mar 7 - Mar 14
found 14 hours ago
Roundtrip flight included
Charlotte (CLT) to Pensacola (PNS)
Book a stay at this beach condo in Pensacola Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Pensacola Beach Boardwalk and Pensacola Beach Gulf Pier are located nearby.
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Price was $1,370, price is now $1,010 per person
$1,010
per person
Mar 27 - Mar 30
found 4 hours ago
Roundtrip flight included
Minneapolis (MSP) to Pensacola (PNS)
Stay at this hotel in Pensacola. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Seville Square and Destination Archaeology Resource Center are located nearby.
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Price was $1,127, price is now $845 per person
$845
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Gulf Pier and Casino Beach are located nearby.

Oak Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
El Matador

El Matador

4 out of 5
Okaloosa Island
Save 100% on your flight
Price was $1,143, price is now $796 per person
$796
per person
Mar 30 - Apr 3
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Pensacola (PNS)
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Downtown Pensacola
Price was $1,370, price is now $1,010 per person
$1,010
per person
Mar 27 - Mar 30
found 4 hours ago
Roundtrip flight included
Minneapolis (MSP) to Pensacola (PNS)
Emerald Isle

Emerald Isle

3 out of 5
Villa Primera
Save 100% on your flight
Price was $1,328, price is now $985 per person
$985
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Villa Sabine
Price was $1,127, price is now $845 per person
$845
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)

Oak Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Okaloosa Island
Save 100% on your flight
Price was $1,138, price is now $771 per person
$771
per person
Mar 29 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pensacola (PNS)
Hotel Indigo Orange Beach - Gulf Shores by IHG

Hotel Indigo Orange Beach - Gulf Shores by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,314, price is now $885 per person
$885
per person
Mar 7 - Mar 14
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)
El Matador

El Matador

4 out of 5
Okaloosa Island
Save 100% on your flight
Price was $1,772, price is now $1,247 per person
$1,247
per person
Apr 4 - Apr 11
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,774, price is now $1,251 per person
$1,251
per person
Mar 23 - Mar 30
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)

Top Flight Deals

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

Spirit Airlines
Wed, Feb 25 - Wed, Mar 4
DFW
Dallas-Fort Worth Intl.
PNS
Pensacola Intl.
$94 Roundtrip, found 1 day ago
$94
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Feb 25 from Dallas-Fort Worth Intl. to Pensacola Intl., returning Wed, Mar 4, priced at $94 found 1 day ago
Spirit Airlines
Thu, Feb 5 - Wed, Feb 18
ATL
Hartsfield-Jackson Atlanta Intl.
PNS
Pensacola Intl.
$154 Roundtrip, found 6 days ago
$154
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Thu, Feb 5 from Hartsfield-Jackson Atlanta Intl. to Pensacola Intl., returning Wed, Feb 18, priced at $154 found 6 days ago
Frontier Airlines
Mon, Feb 23 - Mon, Mar 2
BWI
Baltimore Washington Intl. Thurgood Marshall
PNS
Pensacola Intl.
$160 Roundtrip, found 3 days ago
$160
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Baltimore Washington Intl. Thurgood Marshall to Pensacola Intl., returning Mon, Mar 2, priced at $160 found 3 days ago
Spirit Airlines
Tue, Feb 17 - Wed, Feb 18
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$169 Roundtrip, found 5 days ago
$169
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Tue, Feb 17 from O'Hare Intl. to Pensacola Intl., returning Wed, Feb 18, priced at $169 found 5 days ago