Callaway Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Callaway
Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Pensacola - University Area by IHG
Northeast Pensacola
€652
per person
9 Oct - 11 Oct
found 1 day ago
Return flight included
Chicago (ORD) to Pensacola (PNS)
9/10 Wonderful! (791 reviews)
Very helpful and friendly staff. Comfortable room. Clothes left in the room... A worn robe was behind the bathroom door
Reviewed on 31 Aug 2026
The Pensacola Beach Resort
Villa Sabine
€1,017
per person
9 Oct - 11 Oct
found 1 day ago
Return flight included
Chicago (ORD) to Pensacola (PNS)
9.6/10 Exceptional! (3,477 reviews)
This resort was beautiful and in a quiet section of Pensacola Beach. I stayed for a weekend getaway and completely enjoyed my stay. The food in the restaurant was really good and the service was fantastic.
Reviewed on 1 Sept 2026
Landing Apartments - North Central Pensacola
€658
per person
9 Oct - 11 Oct
found 1 day ago
Return flight included
Chicago (ORD) to Pensacola (PNS)
10/10 Exceptional! (12 reviews)
Amenities were solid (gym, swimming pool, filtered water machine, clubhouse). Nice apartment overall, able to cook and WFH with no issue. Parking was ample, residents were friendly. Will definitely be staying here again.
Reviewed on 16 Aug 2026
Surf & Sand Hotel
€712
per person
9 Oct - 11 Oct
found 1 day ago
Return flight included
Chicago (ORD) to Pensacola (PNS)
8.8/10 Excellent! (3,262 reviews)
Breakfast, staff, and beach/pool were great. Staff were pleasant and helpful. We did have an issue with our door that required maintenance to change batteries and do other work. All was resolved satisfactorily.
Reviewed on 31 Aug 2026
Top hotels in Callaway
Holiday Inn Express Hotel & Suites Panama City-Tyndall by IHG
5627 E Highway 22 State Route Panama City FL
Fully refundable
€92
3 Oct - 4 Oct
includes taxes & fees
Chateau Beachfront Hotel, A By The Sea Resort
12525 Front Beach Rd Panama City Beach FL
Fully refundableReserve now, pay when you stay
€55
3 Sept - 4 Sept
includes taxes & fees
7/10 Good! (2,085 reviews)
"Beach view awesome"
Reviewed on 1 Sept 2026
Boardwalk Beach Hotel
9600 S Thomas Dr Panama City Beach FL
Fully refundableReserve now, pay when you stay
€70
23 Sept - 24 Sept
includes taxes & fees
6.8/10 (2,551 reviews)
"When I booked the room online, there was no information disclosed regarding an additional $50 fee for guests under the age of 25. I am 20 years old and active-duty military, and I was not made aware of this charge until I arrived at the property. I was then required to pay a non-refundable $50 fee, ..."
Reviewed on 2 Sept 2026
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.
What to do in Callaway
Sunset Cruise with Good Jibez Only in Panama City Beach
€39
per adult
98% of travellers recommend
Scream Machine l - Xtreme Thrill Ride at Panama City Beach
€60
per adult
72% of travellers recommend
Frequently asked questions
How much does a Callaway holiday package cost?
You can snap up a holiday package to this destination from €652 on Expedia. However, how much your holiday 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'd like to book a cheap Callaway holiday package, consider travelling in February, November and December. You're likely to find lower rates on accommodation and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Callaway?
With a well-organised itinerary, you can easily tick off the main Callaway attractions in a handful of days. But if you want to discover hidden spots or take day trips, consider booking your Callaway holiday for longer.
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 holiday as a package?
You can enjoy significant savings on your Callaway retreat by booking a personalised holiday 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 holiday 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.
How to plan a trip to Callaway?
- Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Callaway.
- Plan your budget wisely: Besides the price of your hotel, you'll need to factor in other expenses. These include flights, food and transportation. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Callaway.
- Decide your trip length: Think about how much time you'd like to spend discovering Callaway. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customised Callaway holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
