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Josephine Vacation Packages

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Josephine Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Pensacola Airport North – I-10 by IHG

Holiday Inn Express & Suites Pensacola Airport North – I-10 by IHG

2.5 out of 5
per person
Jun 5 - Jun 10
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
Stay at this hotel in Pensacola. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions University Town Plaza and Cordova Mall are located nearby.
Summer House West Condos

Summer House West Condos

4 out of 5
Save 100% on your flight
per person
May 31 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
Stay at this 4-star condo in Gulf Shores. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Gulf Shores Beach and Gulf State Park are located nearby.
Sandy Cheeks

Sandy Cheeks

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Stay at this 4-star vacation home in Orange Beach. Enjoy free WiFi, free parking, and mini golf on site. Popular attractions Gulf Shores Beach and Orange Beach Beaches are located nearby.
Phoenix II Condos

Phoenix II Condos

4 out of 5
Save 100% on your flight
per person
May 31 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
Stay at this 4-star condo in Orange Beach. Enjoy free WiFi, a fitness center, and parking (surcharge). Popular attractions Gulf Shores Beach and Orange Beach Beaches 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
per person
May 17 - May 21
found 3 hours ago
Roundtrip non-stop flight included
Madison (MSN) to Pensacola (PNS)
Stay at this 4-star 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.
Pensacola Suites Hotel

Pensacola Suites Hotel

3 out of 5
per person
Jun 5 - Jun 10
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
Stay at this 3-star business-friendly hotel in Pensacola. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cordova Mall and Roger Scott Athletic Complex are located nearby.
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 2 - Jun 6
found 4 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
Stay at this 3.5-star hotel in Pensacola. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Seville Square and Destination Archaeology Resource Center are located nearby.
White Caps Condos

White Caps Condos

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Stay at this 4-star beach condo in Orange Beach. Enjoy free WiFi, a beach locale, and a fitness center. Popular attractions Orange Beach Beaches and The Wharf are located nearby.

Josephine Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
per person
Jun 12 - Jun 16
found 21 hours ago
Roundtrip flight included
Chicago (ORD) 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
per person
May 17 - May 21
found 3 hours ago
Roundtrip non-stop flight included
Madison (MSN) to Pensacola (PNS)
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Downtown Pensacola
Save 100% on your flight
per person
Jun 2 - Jun 6
found 4 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
LUXURY Penthouse Style Condo 2

LUXURY Penthouse Style Condo 2

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Spokane (GEG) to Pensacola (PNS)

Josephine Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Pensacola Airport North – I-10 by IHG

Holiday Inn Express & Suites Pensacola Airport North – I-10 by IHG

2.5 out of 5
per person
Jun 5 - Jun 10
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Villa Sabine
Save 100% on your flight
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
LUXURY Penthouse Style Condo 2

LUXURY Penthouse Style Condo 2

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)

Top Flight Deals

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

Spirit Airlines
Sun, May 25 - Thu, May 29
DFW
Dallas-Fort Worth Intl.
PNS
Pensacola Intl.
$108 Roundtrip, found 3 days ago
$108
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sun, May 25 from Dallas-Fort Worth Intl. to Pensacola Intl., returning Thu, May 29, priced at $108 found 3 days ago
Spirit Airlines
Wed, Apr 23 - Wed, Apr 30
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Apr 23 from O'Hare Intl. to Pensacola Intl., returning Wed, Apr 30, priced at $153 found 1 day ago
Spirit Airlines
Tue, Apr 22 - Mon, Apr 28
BWI
Baltimore Washington Intl. Thurgood Marshall
PNS
Pensacola Intl.
$181 Roundtrip, found 4 days ago
$181
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Apr 22 from Baltimore Washington Intl. Thurgood Marshall to Pensacola Intl., returning Mon, Apr 28, priced at $181 found 4 days ago
Spirit Airlines
Sat, May 31 - Tue, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
PNS
Pensacola Intl.
$190 Roundtrip, found 3 days ago
$190
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sat, May 31 from Hartsfield-Jackson Atlanta Intl. to Pensacola Intl., returning Tue, Jun 3, priced at $190 found 3 days ago