The Ultimate Guide to Booking Southwest Vacations – Will It Save You Money?

BY 

Katie Seemann

- UPDATED: September 28, 2020

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Southwest started as a budget airline but has blossomed into a solid choice for both domestic and Caribbean travel. They offer a great frequent flyer program, a generous flight change and cancellation policy — and they don’t charge fees for checked luggage!

In addition, Southwest offers vacation packages. These package deals consist of a hotel and flight plus extras like rental cars and activities. Let’s take a look at what they offer and explore whether these vacation packages are a good deal.

What Is Southwest Vacations?

Southwest Vacations offers package deals that include both a hotel stay and flight. You can add extras to your package including rental car, airport transfers, insurance, and even activities in your destination city.

How to Find Southwest Vacations

There are 2 ways to access Southwest Vacations.

First, you can go to the Southwest website and click on Flight|Hotel|Car|Vacations in the main menu. Then click on Vacations.

You can also visit SouthwestVacations.com. The search interface in these 2 different methods will be a little different, but you will get to the same results page either way.

How to Book a Southwest Vacation Package

Choose a Hotel

From the Southwest Vacations home page, input your departure and destination cities, dates of travel, and number of travelers. Then click Find The Best Package Deal.

Image courtesy of Southwest Vacations.This will take you to the search results page for hotels in your selected city. The filtering options are located to the left. You can filter by:

• Hotel name
• Price
• Rating
• Hotel amenities (including fitness facilities, pool, free breakfast, spa services, and more)
• Experience (adults only, beach, family, golfing, etc.)
• Distance from points of interest

Hot Tip: Southwest flies to many international destinations, so you might be surprised at the locations you can access through Southwest Vacations! For more information, check out all of these International destinations that Southwest flies to for some vacation inspiration.

Sort the results list alphabetically, by price, or by top picks using the drop-down box at the top.

There is a map view you can access at the top left side of the screen. Click on View these hotels on a map to see the map. (In theory…I could never actually get this map to pop up!)

Each listing also has a map button you can click to see that particular hotel on a map view.

The prices listed are per person and include hotel, flight, and taxes. You might also notice a per month price — this is referring to Southwest Vacation’s pay over time plan called UpLift (more information on this below).

From here you will be able to select your room type. Any additional charge for a room upgrade will be visible at the right side of your screen.

Choose Keep to stay with your current selection, or Select to choose a new room.

Any promotions available for each room type will be listed in the center of the list. These can be slightly deceiving — when I clicked on the promotion labeled Save up to 65%, I got a message that this was already reflected in the price.

And the promotion called Unlimited Luxury Inclusions included things the hotel offers to everyone, like daily maid service and “no wristbands required.”

If you need to make a change to your hotel selection at any time in the process, you can click Modify Hotel at the top of the page.

Choose a Flight

Next you will be prompted to choose a flight. You will see your hotel selection at the top of the page, with your flight options listed below. Filter your results with options at the left and sort using the drop down box at the top.

Your current flight selection will be marked in green, and some flight options may have higher prices.

The price will be clearly listed to the right, but the higher priced options aren’t labeled as such — so you need to pay attention to your original price quote!

All price quotes will include the least expensive Wanna Get Away fares, but you can switch to an Anytime or Business Select fare if you want.

Click on view flight details to see flight numbers and times, then click Select to continue. Repeat the process to choose your return flight.

Hot Tip: You will still be able to earn Southwest Rapid Rewards points on the flight portion of your Southwest Vacations package!

Next you will be able to review your hotel and flight choices, plus add extras like airport transfers, travel insurance, rental cars, and things to do.

Your vacation package price will now be listed in total for all people including taxes and fees (on previous pages, it’s listed per person).

Rental Car

To add a rental car to your vacation package, click Cars at the top of your screen.

Available options will be listed in the middle of your screen with filtering options to the left. The price listed is the total price for the rental car (per day price will be listed right underneath).

After choosing your car, click Select to continue.

You may see a note that states, “Personal Liability Insurance is mandatory unless renter’s credit card has Personal Liability Insurance coverage.”

Hot Tip: There is not an option to add extra car rental coverage through Southwest Vacations, so it’s best to use a credit card that offers great car rental coverage.

The Chase Sapphire Preferred® Card offers primary rental coverage, which means you do not need to make a claim with your personal insurance first.

Credit Card

Benefits & Info

Chase Sapphire Preferred® Card Apply Now (at Chase's secure site)

Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. Earn 2x points on travel and dining at restaurants worldwide, eligible delivery services, takeout and dining out Earn 1 point per dollar spent on all other purchases. Get unlimited DoorDash deliveries with a $0 delivery fee and reduced service fees on orders over $12 for a minimum of one year on qualifying food purchases with DashPass, DoorDash's subscription service. Activate by 12/31/21. Good to Excellent Credit Recommended (670-850) Annual Fee: $95 Must Reads: For more info on the Chase Sapphire Preferred, see our thoughts on its benefits, travel insurance coverage, and credit score requirements. Take a look at our full review to see why it's one of our favorite Chase credit cards.

Airport Transfers

Airport transfers do not have a separate tab on the main menu, but you can find these options a couple of ways.

First, they can be found by scrolling down on the review page after making a car, flight, or hotel selection. You can also find them under the Things To Do tab.

Click the yellow View options button to select the number of passengers and add the transfer to your vacation package.

Travel Insurance

Travel insurance can also be tricky to find. The options are listed after you make a car, flight, or hotel selection, or you can find them under the Things To Do tab.

For each type of coverage, you can click on More to get all the details about the policy. Click on View options to select the number of passengers and add it to your vacation package.

Whether or not you need insurance is an entirely separate discussion. While I personally have never purchased travel insurance, there are definitely some times when it can make sense.

One alternative to purchasing a separate travel insurance policy is to purchase your vacation package using a credit card that offers insurance. There are lots of credit cards out there that offer different levels and types of coverage, including:

• Travel Accident Insurance
  • Offered by the American Express® Gold Card, Chase Sapphire Preferred® Card, and more!
• Trip Cancellation Insurance
  • Offered by the Ink Business Preferred® Credit Card, Chase Sapphire Preferred® Card, and more!
• Lost Luggage Insurance
  • Offered by The Platinum Card® from American Express, Ink Business Preferred® Credit Card, and more!
• Trip Delay Insurance
  • Offered by the Ink Business Preferred® Credit Card, Chase Sapphire Preferred® Card, and more!

Hot Tip: Travel insurance can be a little overwhelming, so we created 3 guides to make it a little easier to understand. For a full breakdown of what type of insurance comes with what credit card, check out our complete guide to credit card insurance. If you think you might need to purchase an additional policy, refer to our guide to buying travel insurance. You will be able to find the right coverage for your situation in no time! If you want to know exactly which company is right for you, see our list of best travel insurance companies. 

Things to Do

To add activities to your Southwest Vacation package, click on Things to Do in the main menu. Scroll down and you will see a list of available activities.

Click on More to see all details about each activity, and click View options to select the number of people and to add the activity to your vacation package.

Complete Your Purchase

After you have made all of your selections, click Checkout in the main menu.

From here you will be able to scroll through all of your selections, modify any details, and see a breakdown of prices.

If you haven’t already, you can add a promotion code at the bottom of this page, right underneath the price breakdown. Click Continue to move on to finalize payment and traveler information.

Lowest Price Promise

Southwest Vacations offers a Lowest Price Promise on their packages, but it only applies to a price change on the SouthwestVacations.com website — not to a similar package offered by a different company.

If you find an identical package on SouthwestVacations.com, you are eligible to receive the difference in price in the form of a travel credit code good for future travel.

To qualify, the lower priced package needs to be identical in every way, including dates, flight numbers, fare type, hotel room category, car rental company and class, and any activities included in the reservation.

If you find an identical package and want to submit a claim, call customer care at 800-243-8372 at least 1 day prior to your departure date.

Travel Credit Code

If you are issued a travel credit code from a Lowest Price Promise claim, it will be emailed to the primary contact on the reservation within 7-10 business days.

Unfortunately, it is pretty restrictive. It’s only valid for the same travel party as the original trip when traveling together on a future vacation package.

Hot Tip: Not sure which credit card is right for you? Check out our guide to the best credit cards for Southwest Airlines Flyers to find the right one for your situation.

Canceling or Changing a Vacation Package

So, life got crazy and now you have to cancel or change your Southwest Vacation package? Here’s what you need to know.

While Southwest Vacations technically does not charge any cancellation or change fees, any package that is canceled or modified is subject to supplier fees up to 100% of your purchase price.

So, any time you cancel or change a Southwest Vacation package, you could be on the hook for the entire price!

If your package includes a flight, that portion of the package is non-refundable, but it can be exchanged. You will be able to use that money toward another flight on Southwest Airlines.

Any cancellations must be made prior to departure. If you are within 24 hours of your trip, call 1-800-775-7105 to cancel.

Refund requests must be made in writing within 90 days of the scheduled departure date. Email your refund request to [email protected]

No refunds will be given for the following:

• Unused or missed flights, hotel days, or rental car days
• Unused, missed, or canceled lift tickets, show tickets, or theme park passes

Bottom Line: Southwest Vacations does not charge any cancellation or change fees, but you are subject to supplier penalty fees that may be up to 100% of your purchase price!

UpLift

UpLift is a service that breaks down your payments into 12 monthly installments. To take advantage of this payment option, select UpLift Pay Monthly during the checkout process.

Before you get too excited, make sure you know what you are getting into. This is a loan service that charges fees, so you will end up paying more in the long run.

Plus, you won’t be earning any valuable points by paying for your vacation with a great credit card!

How UpLift Works

To qualify for UpLift, you must be at least 18 and provide a valid U.S. address, phone number, full name, email address, date of birth, and the last 4 digits of your social security number.

Hot Tip: Before you are approved for UpLift, there will be a soft pull on your credit report, but it won’t effect your credit score.

Paying through UpLift will come with a minimum 4.99% interest rate and a 2% origination fee. If you miss a payment, you will be charged a $15 late fee and will get a negative hit on your credit report.

Taking on interest charges to pay over time is never a great idea, especially for a luxury purchase like a vacation. Instead, we recommend purchasing your Southwest Vacation package with a great travel credit card like the Chase Sapphire Reserve that earns 3x points on travel purchases.

Keep in mind that you need to pay off your credit card bill in full every month to avoid interest charges and damages to your credit.

How to Contact Southwest Vacations

If you need to contact Southwest Vacations during your trip, call 1-800-775-7105 for 24-hour traveler assistance.

To contact customer service before your vacation, call 1-800-243-8372 within the U.S. or 1-414-934-3017 internationally. Customer service representatives are available:

• Monday through Friday 8:00 am – 9:00 pm CST
• Saturday and Sunday 10:00 am – 6:00 pm CST

You can email questions to [email protected] before your vacation. For any questions after your trip has occurred, email [email protected].

Southwest Vacations Promo Codes and Sweepstakes

Southwest Vacations Promo Codes

There are a few ways to find promo codes for Southwest Vacations packages.

1. First, go to SouthwestVacations.com. In the main search box, you will see a field to input your promo code, labeled Promotion code (find). Click on find to view any current promo codes that are being offered.

   

2. Go to SouthwestVacations.com and click on Deals in the main search bar at the top. Then select Promo code deals.

   

3. You can also search for Southwest Vacations promo codes on coupon sites like Retail Me Not or Valpak.

Southwest Vacations Sweepstakes

If you are feeling lucky, enter the monthly sweepstakes from Southwest Vacations!

Each month Southwest Vacations gives away a trip to 1 lucky winner. You don’t need to make a purchase to enter, so check back often for new prizes.

1. To enter, go to the Southwest Vacations home page, scroll all the way down to the bottom, and click on Sweepstakes.

   

2. Then click Enter Now to fill out the entry form for the current sweepstakes.

   

Rapid Rewards Promotions and Vacations Plus

Rapid Rewards Promotions

Often, you can earn bonus Rapid Rewards points for booking a Southwest Vacations package deal. Just click on Rapid Rewards in the main menu to view any current Rapid Rewards promotions.

Vacations Plus

Vacations Plus is a paid upgrade service that includes:

• $200 room upgrade credit (subject to availability)
• Private transportation to and from your resort
• Vacation coach
• 5,000 bonus Rapid Rewards points

The Vacations Plus package costs $179.99 and is available at 3 partner resorts: El Dorado Spa Resorts & Hotels, select Hard Rock Hotels, and Royalton Luxury Resorts.

5,000 Rapid Rewards points are worth about $75-$85. Depending on the cost of ground transportation and whether you can get a room upgrade, this package could be an OK deal.

However, much of the value of Vacations Plus comes from the potential room upgrade. Since this isn’t guaranteed, this package has the potential to be a waste of money.

If you do find that the Vacations Plus package is a good deal for you, you can add it from the Things To Do tab after choosing a participating hotel.

Are Southwest Vacations a Good Deal?

Now that you know what Southwest Vacations are, how they work, and how to book one, let’s look at one of the most important factors in the equation — will a Southwest Vacation package save you money?

I priced out a couple different packages including a hotel stay, flights, and rental car. Here is what I found.

Package #1

The first package was for a weeklong stay in Cancun at the Hotel Riu Palace Las Americas plus Southwest flights for 2 and a Budget rental car.

As you can see, booking this Southwest Vacations package that includes a hotel, rental car, and flights for 2 people saves $203.97.

The rental car cost $70 through Southwest Vacations, but only $62.54 through Budget. So you could save an additional $7.46 by booking the rental car directly through Budget instead of adding it to the package.

Package #2

The next package I priced out was for a chain hotel. These types of hotels (including Marriott and Hyatt properties) often offer lower prices to their members, so I wanted to see how Southwest Vacations stacked up to those prices.

Hot Tip: One thing to remember if you book a hotel as part of a vacation package is that you will likely not earn any hotel loyalty points, and any elite status you have might not be recognized.

This package was for a weeklong stay at the Courtyard Fort Lauderdale Beach plus flights and a Dollar rental car for 2 people.

In this instance, the package including hotel, flights, and rental car costs $241.61 more than booking everything separately.

There are 2 reasons why the package is so much more than booking everything separately.

First, the separate booking includes Marriott member pricing. It’s free to join Marriott Bonvoy, so this is a price that really is accessible to everyone.

Second, booking the rental car with the package costs $222 — but booking the same car through Dollar costs $166.22.

As you can see, you can save money with Southwest Vacations, but not always. In both of these examples, the rental car was more expensive through Southwest Vacations, so it’s probably best to book those separately.

Also, anytime you’re looking at a chain hotel that has a loyalty program, you will probably get better pricing booking directly.

As with anything, I would suggest pricing out your specific package separately before purchasing to ensure you are getting a good deal.

Bottom Line: Booking a Southwest Vacation package can save you money — sometimes! Rental cars tend to be cheaper when booked separately. Also, if your package includes a chain hotel that offers a rewards program like Marriott, Hilton, or Hyatt, it’s usually best to book directly. You will be able to take advantage of lower members-only pricing and earn hotel loyalty points.

Final Thoughts

Southwest Vacations offers deals on travel packages that can include hotels, Southwest flights, rental cars, insurance, airport transfers, and activities. While these packages don’t always save you money, sometimes they do offer lower pricing versus booking separately.

Before booking a Southwest Vacation package, take into consideration their rigid change and cancellation policy. Sometimes, it might be worth spending a little extra to be able to cancel or change your reservation without penalty.

Since these packages don’t always offer the best deal, it’s smart to price out everything individually before purchasing a package to make sure you are getting a good deal.

Featured image: courtesy of southwest.com