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Jay Vacation Packages

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Jay Flight + Hotel Packages

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

El Matador

4 out of 5
Save 100% on your flight
Price was $1,392, price is now $977 per person
$977
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pensacola (PNS)
Stay at this condo in Fort Walton Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Okaloosa Island Beach and Liza Jackson Park are located nearby.
Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Save 100% on your flight
Price was $1,580, price is now $1,026 per person
$1,026
per person
Mar 27 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Walton Beach (VPS)
Stay at this aparthotel in Miramar Beach. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Sandestin Golf Resort - Raven, Burnt Pine, Baytowne, The Links and Miramar Beach are located nearby.
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Save 100% on your flight
Price was $1,581, price is now $1,063 per person
$1,063
per person
Mar 27 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Okaloosa Island Beach and HarborWalk Village are located nearby.
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,025, price is now $1,381 per person
$1,381
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Walton Beach (VPS)
Book a stay at this beach condo in Miramar Beach. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Sandestin Golf Resort - Raven, Burnt Pine, Baytowne, The Links and Miramar Beach are located nearby.
Emerald Isle

Emerald Isle

3 out of 5
Save 100% on your flight
Price was $1,838, price is now $1,298 per person
$1,298
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Portofino Island Resort

Portofino Island Resort

4 out of 5
Save 100% on your flight
Price was $1,997, price is now $1,426 per person
$1,426
per person
Mar 21 - Mar 27
found 2 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) 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 Park East On-Leash Dog Beach and Tiger Point Golf and Country Club 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 $1,460, price is now $1,049 per person
$1,049
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Washington (DCA) 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.

Jay Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Price was $788, price is now $553 per person
$553
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Walton Beach (VPS)
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 $1,460, price is now $1,049 per person
$1,049
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Washington (DCA) to Pensacola (PNS)
El Matador

El Matador

4 out of 5
Okaloosa Island
Save 100% on your flight
Price was $1,165, price is now $837 per person
$837
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)

Jay Vacation Packages 5-7 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 $1,392, price is now $977 per person
$977
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pensacola (PNS)
Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Save 100% on your flight
Price was $1,580, price is now $1,026 per person
$1,026
per person
Mar 27 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Walton Beach (VPS)
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 $1,581, price is now $1,063 per person
$1,063
per person
Mar 27 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pensacola (PNS)
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,025, price is now $1,381 per person
$1,381
per person
Apr 5 - Apr 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Walton Beach (VPS)

Top Flight Deals

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

Frontier Airlines
Sat, Feb 28 - Wed, Mar 4
DFW
Dallas-Fort Worth Intl.
PNS
Pensacola Intl.
$156 Roundtrip, found 4 days ago
$156
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Feb 28 from Dallas-Fort Worth Intl. to Pensacola Intl., returning Wed, Mar 4, priced at $156 found 4 days ago
Spirit Airlines
Sun, Apr 5 - Thu, Apr 9
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sun, Apr 5 from O'Hare Intl. to Pensacola Intl., returning Thu, Apr 9, priced at $179 found 2 days ago
Spirit Airlines
Mon, Feb 9 - Wed, Feb 18
ATL
Hartsfield-Jackson Atlanta Intl.
PNS
Pensacola Intl.
$181 Roundtrip, found 1 day ago
$181
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Feb 9 from Hartsfield-Jackson Atlanta Intl. to Pensacola Intl., returning Wed, Feb 18, priced at $181 found 1 day ago
Frontier Airlines
Sun, Feb 22 - Sat, Feb 28
DCA
Ronald Reagan Washington National
PNS
Pensacola Intl.
$191 Roundtrip, found 3 days ago
$191
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Feb 22 from Ronald Reagan Washington National to Pensacola Intl., returning Sat, Feb 28, priced at $191 found 3 days ago