Southwest Vacations Guide: Does it Really Save you Money? [2020]

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Are you looking for ways to save on your next vacation?

Well, if you travel Southwest Airlines then you might want to look into using “Southwest Vacations.” Southwest Vacations is a special portal where you can book packages such as flight and hotel or flight and rental car packages and save some serious cash.

However you may not always be saving money and so you want to know how to get the most out of this program.

Below, I will show you some real world examples that I found on this portal when researching and give you some insight into what types of packages might be the most worthwhile. I’ll also answer a lot of common questions about these packages.

What is Southwest Vacations?

Southwest Vacations is the leisure vacation package product for Southwest Airlines. They offer special travel packages that you can purchase to save money by bundling your bookings together, such as flights, hotels, car rentals, and activities. 

The packages come in different forms but you can buy package deals for flights and hotels or flights and car rentals. You can also lump in activities and jump on special promo deals throughout the year to maximize savings.

How do you use Southwest Vacations?

  • Step one: Navigate to the Southwest Vacations website
  • Step Two: Choose the type of vacation package you’re interested in
  • Step Three: Enter your travel details
  • Step Four: Sort and locate your desired bookings
  • Step Five: Confirm your booking details
  • Step Six: Checkout 

Navigate to Southwest Vacations

Choose the type of vacation package you’re interested in

On the main Southwest Vacations homepage, you’ll be able to select the type of vacation package you are interested in by selecting one of three tabs. 

Screenshot of menu showing different types of travel packages
Southwest offers different types of travel packages.

It’s possible to add on more to your package at the time of checkout. For example, you can add a rental car to a flight and hotel package or even add activities. 

Enter your travel details

You’ll need to enter in your travel destinations as well as your planned departure and return dates. You can also select the specific details for your package such as the number of adults and rooms needed. Don’t forget that Southwest now travels to many international destinations.

Sort and locate your desired bookings

Once you have input your travel details, you’ll be able to sort through a lot of travel bookings.

If you are choosing a flight and hotel package, you will choose your hotel stay first and then your flights. If you are booking a flight and rental car, you will choose your flight first.

Using the panel on the left side, you can search and filter hotels by price, star rating, map location, amenities, experience, etc. You can also sort by price and/or rating.

If you are booking a rental car, you can filter by lots of different brands for rental car companies, such as Alamo, Budget, Dollar, Enterprise, Hertz, and National. You can also filter by car type and class such as compact, fullsize, etc.

Confirm your booking details

Once you have selected your entire travel package, you will see a breakdown of all of your bookings before you make your payment.

This is an important page because it is where you can confirm the details of things like the hotel cancellation policy.  

Screenshot of a hotel cancellation policy
Be sure to check your hotel cancellation policies before booking!

You can also add travel protections if needed.

Note that the terms make clear that flights may be nonrefundable and that your refund will be issued in the form of an airline credit for future travel. This is even the case if you purchase insurance for trips disrupted by hurricanes. (This is typical for a Wanna Get Away fare).

Personally, I rarely ever add these protections because I have such great travel protections with my credit cards.

Checkout 

Check out will be pretty straightforward but you do have the option to add on a few things. If you have not added a rental car or activities, you will have the chance to do that.

You can also choose to add Southwest EarlyBird which will allow you to automatically check in 36 hours prior to departure and give you a better boarding position. Southwest has a unique boarding policy and if you don’t know how it works you should read up on it here. 

EarlyBird can be worth it to secure a better party position for some people.

And finally, there will be an option for a payment plan via Uplift.

At check out you simply select “Pay Monthly.”

But don’t jump on this payment plan too quickly.

When I reviewed the going interest rates they were at 15% APR, so they aren’t exactly among the best.

Personally, I would be very hesitant to go into debt at that interest-rate just for a vacation package.

It’s one thing to go into debt for something like medical expenses or starting up a business, but when you start going into debt for vacation packages like this I don’t think that that is often a good idea.

Plus, if you wanted to go into debt for a vacation package you could try to get approved for a 0% APR credit card and avoid paying interest on those expenses. 

However, you can check your eligibility for the loan without impacting your credit score.

Picture of the castle at Disney World.
Southwest Vacations is easy to use and can offer great deals.

Southwest flight and hotel packages

I was very curious about whether or not the Southwest Vacations packages for flights and hotels would be cheaper than simply booking these individually. So I tested out five random flights and hotel stays to get a sense of the price comparisons.

I made sure that the hotel cancellation policies were identical or at least very close to being identical since sometimes the exact same policy was not listed. However, where there were cancellation policy differences, those are noted.

Package #1

Details

  • LaGuardia Airport (LGA) to McCarran International Airport (LAS) + The Cosmopolitan of Las Vegas 

Prices

  • Southwest flight and hotel packages: $799.81
  • Individual booking: $1,079.46 (Airfare: $591.92; Hotel: $487.54)

Package #2

Details

  • Dallas Love Field Airport (DAL) to Luis Muñoz Marín International Airport (SJU) + San Juan Marriott Resort & Stellaris Casino

Prices

  • Southwest flight and hotel packages: $1,174.41
  • Individual booking: $1,432.92 (Airfare: $850.40; Hotel: $582.52)

Package #3

Details

  • Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO) + Hyatt Regency San Francisco

Prices

  • Southwest flight and hotel packages: $750.46
  • Individual booking: $848.97 (Airfare: $395.92; Hotel: $453.05)

Package #4

Details

  • Seattle-Tacoma International Airport (SEA) to William P. Hobby Airport (HOU) + Hilton Americas-Houston

Prices

  • Southwest flight and hotel packages: $688.82
  • Individual booking: $753.56 (Airfare: $411.92; Hotel: $341.64)

In this case, there was a cancellation deadline difference of three days.

Package #5

Details

  • Phoenix Sky Harbor International Airport (PHX) – Orlando International Airport (MCO) + Universal’s Cabana Bay Beach Resort

Prices

  • Southwest flight and hotel packages: $1023.02
  • Individual booking: $1077.42 (Airfare: $595.92; Hotel: $481.50)

In this case, there was a cancellation deadline difference of four days.

The results

Every vacation package that I tested came back cheaper than booking the airfare and hotel individually. So if you are trying to save money on your flights and hotels, I think Southwest Vacations can be a smart way to book.

One thing I have not been able to verify is whether or not you can earn elite credits and utilize your elite benefits when staying at hotels booked through Southwest Vacations.

If I had to guess, I would say that these bookings are considered to be just like any other online travel agency. That would mean that you would not earn elite credits and that you would have to “fight” for your elite benefits.

If that is the case, then you will have to evaluate whether or not the savings will be worth the loss of benefits. If your hotel elite status would entitle you to breakfast and valuable upgrades then it may not be worth it.

But don’t forget to factor in special earning rates at certain hotels.

For example, Southwest in the summer of 2020 was offering a special promo where you could earn 600 Rapid Rewards points per room for every qualifying stay at Las Vegas M life MGM Resorts International Properties.

Typically, you should you should be able to see these additional earning rates when you are searching for your booking.

A picture of the cosmopolitan hotel suite in Las Vegas.
Flight and hotel packages can be well worth it.

Southwest flight and rental car packages

For the rental car packages, I once again chose five separate packages with random destinations. (To keep things consistent, I focused on Enterprise Rental Car.)

Once again, I compared the prices found on the vacation website to prices found for the identical flights on the main Southwest website and identical vehicles on the Enterprise website. 

In most cases, booking rental cars on an individual basis was cheaper than Southwest Vacations. (And in some cases, it was way cheaper.) So personally, I would not be attracted to the Southwest flight + rental car packages. 

Package #1

Details

  • LaGuardia Airport (LGA) to McCarran International Airport (LAS) + Enterprise Rental Car 

Prices

  • Southwest flight and rental car packages: $781.83
  • Individual booking: $705.64 (Airfare: $591.92; Car: $113.72)

Package #2

Details

  • Los Angeles International Airport (LAX) to LaGuardia Airport (LGA) + Enterprise Rental Car

Prices

  • Southwest flight and rental car packages: $928.17
  • Individual booking: $939.52 (Airfare: $591.92; Car: $347.60)

Package #3

Details

  • Chicago Midway International Airport (MDW) to Fort Lauderdale-Hollywood International Airport (FLL) + Enterprise Rental Car

Prices

  • Southwest flight and rental car packages: $577.19
  • Individual booking: $481.08 (Airfare: $281.92; Car: $199.16)

Package #4

Details

  • Seattle-Tacoma International Airport (SEA) to Chicago Midway International Airport (MDW) + Enterprise Rental Car

Prices

  • Southwest flight and rental car packages: $802.02
  • Individual booking: $617.42 (Airfare: $437.92; Car: $179.50)

Package #5

Details

  • William P. Hobby Airport (HOU) to San Diego International Airport (SAN) + Enterprise Rental Car

Prices

  • Southwest flight and rental car packages: $718.67
  • Individual booking: $627.84 (Airfare: $403.92; Car: $223.92)

Activities

I was curious to see how the prices for activities compared when booking through the Southwest Vacations website or through a third-party website like Viator.

So I found activities that were the same or virtually identical and priced them out against each other. Overall, it looks like booking activities through Southwest Vacations was more expensive on average.

Activity

  • Palm Pleasure Sunset Sail (AUA)

Prices

  • Southwest packages: $158
  • Individual booking: $123.98

Activity

  • Blue Man Group Show at Universal Orlando Resort Tier 1

Prices

  • Southwest packages: $150
  • Individual booking: $159.58

Activity

  • Swim with Whale Sharks from Cancun

Prices

  • Southwest packages: $449.96
  • Individual booking: $380

Activity

  • Turtle Snorkel Sail with Lunch Honolulu

Prices

  • Southwest packages: $282
  • Individual booking: $280.48

Activity

  • Sunset Dinner Cruise in Cabo San Lucas

Prices

  • Southwest packages: $214
  • Individual booking: $178
I would recommend booking activities separately or at least checking price comparisons.

Special deals and promo codes

You can often find special deals and promo codes for Southwest Vacations.

You really have to factor these in since Southwest Vacations can have more expensive prices for certain types of packages. On many occasions, these promotions can make up for that price difference and present a better deal.

These deals will vary throughout the year but here is an example of what you could find during Black Friday and Cyber Week 2018 with promo codes and daily deals.

Book a flight + hotel package to any destination we offer, and save up to $250 at the time of booking.

  • $125 off U.S. vacations with promo code SAVE125DOM*
  • $250 off international vacations with promo code SAVE250INT*

Here’s a look at another promo package that went out in 2020:

  • $125 off U.S. vacations (excluding Hawaii) with promo code 125DOM20.
  • $250 off international vacations with promo code 250INTL20.
  • $250 off Hawaii vacations with promo code 250HI20.

These deals will come with certain types of terms and conditions that limit travel to certain dates. For example, you are the limitations for the 2020 promo:

  • Book: 6/2/2020 – 6/22/2020 by 11:59 p.m. CT
  • Travel for U.S. vacations (excluding Hawaii): 6/3/2020 – 1/4/2021
  • Travel for international & Hawaii vacations: 7/1/2020 – 1/4/2021

Other times you can find special deals for certain destinations, such as Mexico or Las Vegas. Other popular destinations that often have deals are tourist hot spots in Florida like Disney World and Universal Studios. You can search for the current deals here.

Southwest Vacations FAQ

Can I cancel a Southwest Vacations package?

Yes, you can cancel a Southwest Vacations package but it may come at a cost. Flights may be refunded in the form of travel credits and hotel cancellations may result in fees if not canceled before the cancellation window which may be 24 to 48 hours or more prior to check out.

Can I make changes to my Southwest Vacations package?

Yes, you can make changes to your reservation. However, you cannot make changes to flights less than one day prior to departure. In order to make changes, it’s recommended to call the customer care center at 1-800-243-8372 during our regular operating hours. 

Can I add activities to my Southwest Vacations package?

Yes, you can add activities to your vacation package even after you have made your booking. Simply call the customer care number to process your changes.

Can I use Southwest Rapid Rewards points to book a Southwest Vacations package?

No, unfortunately you cannot use your Southwest Rapid Rewards towards the purchase price of a vacation package.

Can I use Southwest travel funds on a Southwest Vacations package?

Yes, you can use Southwest travel funds on a Southwest Vacations package that includes air. Funds must be applied at time of initial booking by selecting “Southwest Travel Funds” as your payment type.

What is the Southwest Vacations Coronavirus policy?

Southwest Vacations put into effect a special policy that will automatically provide you with a travel credit if a government’s travel restriction that results in a flight or hotel cancellation. You should receive an email from Southwest Vacations with rebooking instructions. 

You can try calling for more details but be prepared for a long wait times. You read more about the policy here.

What is the Southwest Vacations phone number?

The Southwest Vacations phone number is: 1-800-243-8372.

Final word

The Southwest Vacations deals are worth looking at but you need to make sure that you do some additional research.

You will often find great deals for flight plus hotel packages (especially when you can leverage promo codes), but when you start to throw in other things like rental cars you really need to be sure that you are getting the best deal, since on a couple of occasions Southwest did not offer the best price.

Also when it comes to booking activities, I would stick to booking those individually.

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