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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.
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 $948, price is now $662 per person
$662
per person
Mar 30 - 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.
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 $1,346, price is now $901 per person
$901
per person
Apr 2 - Apr 10
found 4 hours ago
Roundtrip non-stop flight included
Appleton (ATW) to Pensacola (PNS)
Book a stay at this business-friendly hotel in Orange Beach. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Gulf Shores Beach and The Wharf are located nearby.
Landing Apartments Santa Rosa Beach

Landing Apartments Santa Rosa Beach

4 out of 5
Save 100% on your flight
Price was $1,441, price is now $968 per person
$968
per person
Mar 29 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Walton Beach (VPS)
Stay at this aparthotel in Santa Rosa Beach. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Seaside Beach and Alys Beach are located nearby.
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,002, price is now $1,376 per person
$1,376
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.
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,478, price is now $1,068 per person
$1,068
per person
Mar 21 - Mar 28
found 4 hours 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.
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Save 100% on your flight
Price was $1,061, price is now $774 per person
$774
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Henderson Beach State Park and Big Kahuna's Water and Adventure Park are located nearby.
Portofino Island Resort

Portofino Island Resort

4 out of 5
Save 100% on your flight
Price was $2,028, price is now $1,492 per person
$1,492
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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.
Beach Club Resort Residence and Spa

Beach Club Resort Residence and Spa

4.5 out of 5
Save 100% on your flight
Price was $1,648, price is now $1,220 per person
$1,220
per person
Mar 21 - Mar 28
found 4 hours 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.

Jay Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Price was $781, price is now $563 per person
$563
per person
Mar 20 - Mar 24
found 21 hours 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 $948, price is now $662 per person
$662
per person
Mar 30 - 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
Price was $792, price is now $577 per person
$577
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Pensacola (PNS)
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Crystal Beach
Save 100% on your flight
Price was $1,061, price is now $774 per person
$774
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)

Jay Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Orange Beach - Gulf Shores by IHG

Hotel Indigo Orange Beach - Gulf Shores by IHG

3.5 out of 5
Price was $788, price is now $533 per person
$533
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Pensacola (PNS)
Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Save 100% on your flight
Price was $1,152, price is now $769 per person
$769
per person
Mar 3 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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 $1,411, price is now $942 per person
$942
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pensacola (PNS)
Landing Apartments Santa Rosa Beach

Landing Apartments Santa Rosa Beach

4 out of 5
Save 100% on your flight
Price was $1,441, price is now $968 per person
$968
per person
Mar 29 - Apr 3
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 21 - Sat, Feb 28
DFW
Dallas-Fort Worth Intl.
PNS
Pensacola Intl.
$141 Roundtrip, found 1 day ago
$141
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Dallas-Fort Worth Intl. to Pensacola Intl., returning Sat, Feb 28, priced at $141 found 1 day ago
Frontier Airlines
Mon, Feb 23 - Mon, Mar 2
BWI
Baltimore Washington Intl. Thurgood Marshall
PNS
Pensacola Intl.
$160 Roundtrip, found 5 days ago
$160
Roundtrip
found 5 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 5 days ago
Spirit Airlines
Sun, Apr 5 - Thu, Apr 9
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$179 Roundtrip, found 8 hours ago
$179
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Sun, Apr 5 from O'Hare Intl. to Pensacola Intl., returning Thu, Apr 9, priced at $179 found 8 hours ago
Spirit Airlines
Mon, Feb 9 - Wed, Feb 18
ATL
Hartsfield-Jackson Atlanta Intl.
PNS
Pensacola Intl.
$181 Roundtrip, found 22 hours ago
$181
Roundtrip
found 22 hours 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 22 hours ago