The Site: SouthwestVacations.com
- Affordable fun vacation packages in exciting destinations from coast to coast
- Southwest Vacations’ packages are combined with cheap Southwest Airlines flights.
- No checked baggage charges. Your first and second checked bags are free! (*under 50 lbs.) - Only airline we know of with a free bag policy.
- Hotel-only bookings available.
- Reserve car rentals, activities and attraction tickets in one complete vacation package.
- Popular destinations include Las Vegas, Los Angeles, Orlando and Reno.
- Search Southwest by “Vacation Themes”. Specialty vacation packages for adventure, culture, family, gaming, golf, ski, spa, sports and more.
- Clickable “Destination Map”. Easily find your closest departure city and all available destinations.
- Destination videos.
- Earn “Rapid Rewards” from Southwest Airlines for every vacation package booked on southwestvacations.com, if you are already a Rapid Reward member. Enroll on the Southwest Airlines site to earn rewards.
The Good:
Southwest Vacations always have inexpensive vacation packages, which are easily found under the “DEALS” tab on southwestvacations.com. All of Southwest Vacations’ current deals are listed, and it is easy to find a cheap vacation package here. Southwest Vacations’ deals are sorted by destination city, so just scroll down and find what looks fun to you. Remember that even if the “departure city” is not yours, you can still click on the deal and then choose your nearest departure city. Quite often, that destination will still be reduced in price.
The Bad:
Southwest Vacations hotel descriptions and ratings are sparse. The good news is that this information is easily found online elsewhere. We recommend that you read hotel reviews and ratings on another site prior to booking, such as Expedia, to make sure the hotel is not a dump! Be advised that you cannot book a “flight only” on the Southwest Vacations site, unless you include a rental car. Not really a bad thing, but this site is dedicated to “packages” of either “flight plus hotel“, “flight plus car“, ect…
The Fees *:
- Variable $30 (up to $100) penalty per person to cancel or change a Southwest Vacations reservation. Must be at least 48 hours prior to departure.
- No refunds on attractions and passes.
- Purchase a “pre-travel waiver” and all Southwest Vacations penalties will be waived if you need to cancel your vacation. Also, you’ll be guaranteed the lowest available rate for the specified travel itinerary.
- Document delivery fee $7.50 per package ONLY if booked LESS than 15 days in advance. Southwest Vacations are not ticketless. Boarding passes can not be issued online or at airport kiosks when traveling on a vacation package. You are required to bring your flight tickets with you to the airport in order to travel.
- No fees for checked bags!
- No fuel surchages.
* Based solely on research done by TravelSiteCritic.com, and may be inaccurate or subject to changes.
The Deals:
Southwest Airlines Vacations Current Deals << CLICK HERE for all updated travel coupon codes
Cheap Disney World vacation packages. Stay 5-Nights in a Disney Hotel, including Flight to Orlando from only $424* per person. Cheapest departures are on Saturday or Monday
Cheap rates on vacation packages to Las Vegas

Don’t even try to make any changes after you book a Southwest vacation. We wanted to see if we could upgrade our hotel room. The hotel said we had to do it through Southwest. Southwest said they couldn’t do it b/c it was less than a week before our vacation. How ridiculous! We would have been better off booking everything separately. I don’t believe we saved any $$ at all booking through Soutwest vacations either.
I feel your pain. I just called to change a vacation I had booked, not minding to pay the extra fees in order to get the dates which worked toward my convenience only to have an incompetent, rude employee misinform me of the policy (which I was under the impression I had to pay just the difference, not have to pay for the new trip IN FULL, to have to await a refund) – Southwest called me back and apologized for giving me misinformation and I was on hold for over an hour and a half. I’m pretty livid and plan on never booking a vacation through them ever again nor will I probably ever book a flight through them either.
I wanted to share my recent experience with Southwest Vacations. The hotels are a great deal- the flights are a different story. We purchased a round trip flight to Vegas, and only after we received confirmation, did they tell us that that flight had a lay over. When we called to change our flight, they told us we could not change or cancel the reservation- no exceptions. Upon further discussions, I learned that I would be snail mailed our airplane tickets- I specifically asked if these would be coming via Fed Ex and need a signature, as I, like most of the world, work all day. They told me “no- it will come via US Mail.” So what happens a few days later, but I get a Fed Ex ticket on my door- saying they cant leave the package without a signature- great. So, I call Southwest Vacation packages, again and ask if there is anyway I can change the Ship to address or have the tickets delivered electronically- I am told NO and NO. Wow… could they make this any more difficult? So, I end nup having to go to Fed Ex, and pick up the tickets myself. Ok- fast forward to day of the travel- I go to check in online- and receive a “fake” boarding pass that tells me I cannot use this to get on the plane, but only to get through security. On the day of my trip, I take the “boarding pass” to security, and am told they cannot let me through with the document, and have to call over their manager.
WHAT A NIGHTMARE. I honestly don’t think that they could have made flying on Southwest any more difficult. Next time, I will skip the vacation package, spend the extra $100, and have a stress free travel experience. I would suggest you do the same
We feel your pain JP. They indeed do try to make traveling with them as difficult as possible. Not even addressing their archaic check in policies, upon trying to buy an early check in pass, we were told we were not allowed to since we purchased a vacation package. This means because we booked in advance and basically thought we were doing something we assumed would result in a stress free vacation, we are being penalized by Southwest. Their claim to be customer service friendly is joke. There’s no friendliness if you have an issue with them. I, too, will think twice about buying a so called Vacation Package from Southwest, and will certainly not be in a big hurry to fly with them.