A wide sandy beach with clear shallow waters and dunes in the background.

Callaway Vacations from $506

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Your Callaway Vacation

The coastal scenery and laid-back lifestyle are just the start of the things Callaway has on offer. Discover the sights and sounds of this captivating city the way you want with a personalized Callaway vacation package. A trip to Callaway is a superb opportunity to sightsee. Make sure you visit renowned attractions like Panama City Mall, Saint Andrews Shopping Center and Cove Shopping Center. A couple of quick clicks is all it takes to put together a tailored Callaway vacation on Expedia.

The Latest Callaway Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 26 - Jan 29

    Hotel Margot + Flight

    Downtown Pensacola
    3 nights
    4.0 star property
    9.4/10 - Exceptional (20 reviews)
    Roundtrip • Minneapolis (MSP) - Pensacola (PNS)
    MSP - VPS • 1 stop VPS - MSP • Nonstop
    $675
    $506
    per traveler
    found 18 hours ago
    Hotel Margot
  • Dec 24 - Dec 29

    Bay Club of Sandestin + Flight

    Miramar Beach
    5 nights
    3.5 star property
    9.0/10 - Wonderful (187 reviews)
    Roundtrip • Dallas (DFW) - Fort Walton Beach (VPS)
    DFW - VPS • Nonstop VPS - DFW • Nonstop
    $1,004
    $736
    per traveler
    found 1 day ago
    Bay Club of Sandestin
  • Dec 24 - Dec 29

    The Pensacola Beach Resort + Flight

    Villa Sabine
    5 nights
    4.0 star property
    9.6/10 - Exceptional (3,710 reviews)
    "This was a lovely place to stay! Very clean, spacious, and beautiful views from the rooms and the lobby. Plenty of places to sit and enjoy the ocean view. Loved the sunrise every morning and the pool was awesome for a morning (uncrowded) swim! The water was warm and the perfect temperature. Breakfast is not included but the onsite restaurant had good breakfast and was reasonably priced. We would definitely stay here again. A great place to relax and enjoy time with friends or family near the..."
    Reviewed November 9, 2026
    Roundtrip • Dallas (DFW) - Pensacola (PNS)
    DFW - VPS • Nonstop VPS - DFW • Nonstop
    $935
    $699
    per traveler
    found 16 hours ago
    The Pensacola Beach Resort
  • Feb 1 - Feb 5

    Camp Creek Inn + Flight

    Panama City Beach
    4 nights
    4.0 star property
    9.8/10 - Exceptional (159 reviews)
    "Beautiful property with fabulous amenities."
    Reviewed October 19, 2026
    Roundtrip • Minneapolis (MSP) - Panama City (ECP)
    MSP - VPS • Nonstop VPS - MSP • Nonstop
    $1,071
    $810
    per traveler
    found 1 day ago
    Camp Creek Inn
  • Jan 21 - Jan 27

    Destin Dream by Avantstay 2-story Home, Walk to Beach + Flight

    Frangista Beach
    6 nights
    3.0 star property
    10/10 - Exceptional (5 reviews)
    "We had such a lovely week here. First time to the Miramar Beach/Destin area. The house was top shelf 10/10 and felt like home for our family. 100% will be back. Everything was too good not to hit “the easy button” and book the same trip again. Host was communicative and helpful in every way. We were overjoyed to make wonderful memories with our kids that we will cherish forever."
    Reviewed October 24, 2026
    Roundtrip • Minneapolis (MSP) - Fort Walton Beach (VPS)
    MSP - VPS • 1 stop VPS - MSP • 1 stop
    $1,597
    $1,217
    per traveler
    found 5 hours ago
    Destin Dream by Avantstay 2-story Home, Walk to Beach

Callaway Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a Callaway vacation package cost?

You can snap up a vacation package to this destination from $506 on Expedia. However, how much your vacation to Callaway costs will depend on your hotel choice, length of stay and season.

What are the cheapest months to go to Callaway?

If you're hoping to snag a cheap Callaway vacation package, consider traveling in November, December and January. You'll usually find better prices on flights and accommodations during these months — ideal for travelers wishing to save money.

How many days is enough for Callaway?

Usually, a handful of days is enough to visit the top sights during your Callaway vacation. However, if you prefer to have more time to unwind or go on day trips, think about extending your trip.

How to find the best Callaway package deals?

Begin your search for a Callaway package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Callaway package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Callaway escape off to a flying start.

Is it cheaper to book a Callaway vacation as a package?

You can enjoy significant savings on your Callaway retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.

When to book a vacation package to Callaway?

If you're planning an impromptu Callaway adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.

Does Expedia offer Book Now, Pay Later Callaway vacation packages?

Secure your ideal getaway to Callaway with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait for the next payday — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snag great deals before they disappear.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.