Skip to main content
A serene lake with a forested island reflecting the sun.

Gulf Pines Vacations from $1,069

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Gulf Pines Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Beach nearby
    Aug 23 - Aug 28

    Hidden Beach Villas + Flight

    Seagrove Beach
    5 nights
    4.0 star property
    8.4/10 - Very Good (26 reviews)
    "Close to beach, pool was awesome, place was awesome"
    Reviewed July 18, 2026
    Roundtrip • New York (EWR) - Destin (DSI)
    EWR - VPS • 1 stop VPS - EWR • 1 stop
    $1,666
    $1,069
    per traveler
    found 1 day ago
    Hidden Beach Villas
  • Outdoor pool, free cabanas
    Aug 23 - Aug 28

    Landing Apartments Santa Rosa Beach + Flight

    Santa Rosa Beach
    5 nights
    4.0 star property
    9.2/10 - Wonderful (12 reviews)
    Roundtrip • New York (EWR) - Destin (DSI)
    EWR - VPS • 1 stop VPS - EWR • 1 stop
    $2,001
    $1,174
    per traveler
    found 1 day ago
    Landing Apartments Santa Rosa Beach
  • On the beach
    Aug 23 - Aug 28

    Beachside Condominiums + Flight

    Seagrove Beach
    5 nights
    3.0 star property
    7.6/10 - Good (5 reviews)
    "The condo was very clean and well maintained! Communication with the host was fast and reliable. There was a nice beach view on the balcony. But my favorite part is that the condo was right on the beach, the walk was less than a minute to the beach. Overall, well worth a stay."
    Reviewed June 1, 2026
    Roundtrip • New York (EWR) - Destin (DSI)
    EWR - VPS • 1 stop VPS - EWR • 1 stop
    $1,793
    $1,192
    per traveler
    found 1 day ago
    Beachside Condominiums
  • House (4 Bedrooms) | Interior
    Aug 23 - Aug 28

    Southern Dreams on 30A by Avantstay Pool + Outdoor Lounge + Golf Cart Access Minutes to the Beach + Flight

    Dune Allen Beach
    5 nights
    3.0 star property
    Roundtrip • New York (EWR) - Destin (DSI)
    EWR - VPS • 1 stop VPS - EWR • 1 stop
    $2,366
    $1,586
    per traveler
    found 1 day ago
    Southern Dreams on 30A by Avantstay Pool + Outdoor Lounge + Golf Cart Access Minutes to the Beach
  • Interior
    Aug 23 - Aug 28

    🌴 Private Backyard Minutes to 30A + Beaches Golf Cart + Bikes The Little Blue Beach House by Avantstay + Flight

    Santa Rosa Beach
    5 nights
    3.0 star property
    Roundtrip • New York (EWR) - Destin (DSI)
    EWR - VPS • 1 stop VPS - EWR • 1 stop
    $2,443
    $1,638
    per traveler
    found 1 day ago
    🌴 Private Backyard Minutes to 30A + Beaches Golf Cart + Bikes The Little Blue Beach House by Avantstay
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.