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Jay Flight + Hotel Packages

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)
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.
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,968, price is now $1,338 per person
$1,338
per person
Apr 5 - Apr 10
found 15 hours 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.
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 $1,173, price is now $800 per person
$800
per person
Feb 28 - Mar 7
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) 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.
El Matador

El Matador

4 out of 5
Save 100% on your flight
Price was $1,366, price is now $938 per person
$938
per person
Mar 29 - Apr 3
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.
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 $1,120, price is now $771 per person
$771
per person
Mar 29 - Apr 3
found 1 day ago
Roundtrip non-stop 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.
30A Inn & Suites

30A Inn & Suites

3 out of 5
Price was $1,047, price is now $732 per person
$732
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
Stay at this hotel in Santa Rosa Beach. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff in our reviews. Popular attractions Sandestin Golf Resort - Raven, Burnt Pine, Baytowne, The Links and Santa Rosa Beach Golf Club are located nearby.
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Save 100% on your flight
Price was $1,529, price is now $1,074 per person
$1,074
per person
Mar 29 - Apr 3
found 1 day ago
Roundtrip 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.

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 $1,394, price is now $983 per person
$983
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
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 $1,173, price is now $800 per person
$800
per person
Feb 28 - Mar 7
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)
Landing Apartments Santa Rosa Beach

Landing Apartments Santa Rosa Beach

4 out of 5
Price was $1,510, price is now $995 per person
$995
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Save 100% on your flight
Price was $1,451, price is now $986 per person
$986
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Walton Beach (VPS)
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,968, price is now $1,338 per person
$1,338
per person
Apr 5 - Apr 10
found 15 hours 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 5 days ago
$156
Roundtrip
found 5 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 5 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 2 days ago
$181
Roundtrip
found 2 days 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 2 days 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