Southwest Vacations: Your Guide to the Best Southwest Airlines Destinations Worldwide

If you’ve watched a program with ads, you’ve seen the insurance commercials. Bundle your home and auto, and save money on your next bill. Seems like a pretty good deal. Now, if only vacations worked the same way … Oh wait, they do! With Southwest Vacation packages, you can find fantastic vacation deals you won’t find elsewhere. And save yourself some time and a headache while you plan.

Whether you’re looking to stay close to home or whip out that passport and kick it in the Caribbean, you can score a great vacation package with Southwest Vacations.

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What Is a Southwest Vacation Package?

Saving money with vacation packages isn’t a surprise—at least, not anymore.

Getting your flight, hotel, and rental car bundled together is good. However, plenty of services offer that, which may make you wonder what Southwest offers that those sites don’t. 

Southwest provides the benefits of a budget airline and incredible flight savings paired with fantastic hotel offers and great deals on car rentals. 

Booking Southwest Vacation packages allow you to purchase all your individual travel expenses together and even occasionally fun destination activities as well.

Bundling your vacation expenses this way can help you save money in the long run. That said, it’s still a good idea to double-check the prices separately to ensure you’re coming away with a win.

Here are a few things to keep in mind when considering your Southwest Vacation package.

  1. You can earn Rapid Rewards Points on the flight portion of your vacation package. However, you cannot use your points toward your vacation package purchase.
  2. Southwest doesn’t charge cancellation fees, but the hotel, rental car, or excursion activities may apply penalties or fees for cancellations.
  3. offers a deals page with a breakdown of discounts and savings, including resort coupons and Southwest Vacations promo codes.

Southwest Vacation Packages

You may be wondering where exactly you can fly with Southwest Vacations packages. The answer includes some pretty exotic destinations that’ll quickly have you searching for the next available flight!

Because while Southwest may not fly overseas to other continents, that doesn’t mean you’re without options.

One booking with Southwest is the only thing standing between you and a vacation to the Caribbean, a sojourn in Mexico, or a quick flight to the mountains of California. 

Tropical Vacations 

Did we have you at the word “tropical”? Point us anywhere with a beach, and we’re there, bathing suit donned and flip flops flopped off in the sand.

Southwest Vacations to the tropics will have you sunbathing on the Mexican coast and chilling in the Caribbean Sea. 

With so much beach and sunshine, you’re not likely to need a rental car to enjoy the best of what these destinations have to offer, but the added Rapid Rewards points will undoubtedly be a bonus, along with the freedom to go anywhere you want. Just don’t forget your beach bag!

Cancun, Mexico

This stunning jewel on the Mexican coast is easily one of the hottest Southwest Vacation destinations.

Cancun is known for its beautiful white-sand beaches and party atmosphere. With Southwest Vacation packages, you can take advantage of both. 

Coming in after a late night out or waking up to a brilliant sun out over the water? Sounds like heaven.

Punta Cana, Dominican Republic

Endless beaches and sunshine make Punta Cana a favorite destination for many, which is why it often trends on Southwest Vacations. 

The perfect weather and blue-green waters invite travelers to stay and discover paradise amidst calm waves and palm-studded views.

Away from the beach, you can explore the wonders of the island and the casinos dotting Punta’s Cana’s luxury resorts.


Aruba is a desert gem in the middle of the Caribbean sea. You won’t find many rainy days here, making it the perfect retreat for a tropical getaway and a hot ticket among Southwest Vacations. 

While searching for your ideal hideaway beach, see if you can spot Aruba’s iconic Divi Divi and Fofoti trees. You’ll find them sprouting out of the dirt and sand, wind-blown, and pointing toward the southwest.

Montego Bay, Jamaica

This Caribbean destination isn’t just a popular port for cruises; it’s also a hot getaway for Southwest Vacations. 

That might have to do with the multitude of resort hotels and duty-free shopping. Additionally, between the gorgeous beaches, lush jungles, and mountain views, you’re in for a treat.

Miami, Florida

If you’re looking for the best Southwest Vacations deals, look no further than one of Florida’s hottest destinations

The vibrant culture and vibes in Miami will make you think you’ve washed ashore on a Caribbean island. Your confusion won’t last long, though. The bold lifestyle and buzzing nightlife will quickly make it clear you’ve arrived in the Magic City. 

Romantic Getaways

If you dream of the perfect romantic getaway with your partner, then a Southwest Vacations package may be just what you need. Prepare to flee your everyday routine and escape into romance. 

With deals to some of the hottest destinations in the US, Caribbean, and Mexico, you’re bound to find your vacation version of happily ever after. 

Grand Cayman

Dive into the wonder that is Grand Cayman Island. You’ll discover endless stretches of sandy beaches, unforgettable encounters with sea creatures, and scuba diving through crystal clear waters. 

With a Southwest Vacation package, you can experience a sunset cruise or swim with stingrays, all while hand-in-hand.

Las Vegas, Nevada

You don’t have to get married in Vegas to take advantage of all its sweet, romantic perks. We’re talking luxury spas, world-class restaurants, and infinite entertainment. 

Las Vegas is the perfect place to get swept away in the glitz, glamor, and lights, and Southwest Vacation packages come with hotel offers for the most luxurious of stays. From the ARIA Resort & Casino to The Venetian, there are plenty of options to make your trip truly pampered.

Providenciales, Turks and Caicos Islands

Romantic retreats don’t always have to be sweet. For a getaway full of adventure, Providenciales is just a flight away.

The perfect weather year-round means you can relax on sandy white beaches, snorkel through turquoise blue waters, and explore the island on a dune buggy with your partner. 

Napa Valley/Sonoma, California

You don’t need to love wine to appreciate the rolling hills and expansive vineyards that make up Napa Valley. 

Napa Valley is perfect for a fun time filled with romantic activities for two. Ride a bike through the scenic beauty, enjoy unique wine tours of the region’s different varieties, or take a trip through the sky on a hot air balloon.

Maui, Hawaii

A warm welcome awaits couples in Maui, the perfect Hawaiian getaway for romance and excitement. Whether you decide to take it easy or get out there and explore, Maui has something for everyone.

Celebrating new moments and shared years among the island’s lush landscapes and before beautiful sunrises are experiences few forget. 

History and Culture Trips

Hoping to bring back some interesting facts and histories to share with your friends and family? 

Vacations that teach you something new or enthrall you in the culture and heritage of a place are the most memorable and rewarding types of trips. 

If your goal is to return wiser than when you left, here are some Southwest Vacation packages you can’t miss.

New Orleans, Louisiana

This quirky city sat on the ​​Mississippi River is a choice stop for fans of US history. It’s also a must-visit for the unique Creole culture. 

Founded by the French, controlled by the Spanish, and purchased by the US, New Orleans’s colored history draws in visitors. 

Whether you lose yourself in the French Quarter or among the many revels that NOLA is famous for, you’re bound to have fun as you learn more about this Southern gem.

Washington, DC

Is there a better place to explore American history than the US capital? 

From soaring monuments to expansive museums making up the largest museum complex in the world, DC is synonymous with US history. 

The fact that it’s become a bustling city with a youthful twist is another reason this city’s popularity refuses to decline among Southwest Vacations. 

Tulum, Mexico

One of the last cities inhabited by the Mayans, Tulum is a rich tapestry of ruins, beaches, sinkholes, and jungles. 

From ruins in Cobá in the heart of the jungle to clifftop El Castillo overlooking the sea, you’ll quickly find yourself caught up in the history and stories of this once great civilization that ruled the Yucatán and beyond.

San Juan, Puerto Rico

Once the Caribbean pearl of the Spanish Empire, San Juan’s dramatic history is still visible today. Colonial forts and Catholic cathedrals still dominate the city, etching its history on its very walls. 

But out of that turbulent history, visitors will be enchanted by the city’s strong Puerto Rican culture. From the Old World to the New, you’ll be fascinated by all San Juan has to offer.

Big Island, Hawaii

The Big Island of Hawaii is home to the only royal palace in the United States—one of the best reasons to book a Southwest Vacation here. But, it’s not the only one. 

Learn about the volcanoes that first formed the Hawaiian Islands and dive deep into the Polynesian culture that shaped its people. 

Hawaii’s history is almost as colorful as the lush islands themselves!

Winter Holiday Retreats

Want to make the most of the snow and cold and escape to a winter wonderland? 

Booking Southwest Vacations to any one of these incredible destinations will have you packing your scarf and boots and preparing for your next winter adventure!   

Vail and Beaver Creek, Colorado

If you plan to ski away your winter holiday, look no further than Vail, one of the biggest ski resorts in North America. The Bavarian-style town and warm atmosphere will help take the winter chill out of the air. You’ll no doubt find yourself equally charmed by the village as you are by its slopes.

And if you simply hail a ride or book a rental car of your choice, you’ll find another famous ski town just a short trip away. Beaver Creek provides fewer busy lifts and slopes to while away your days in the mountains.

Yosemite National Park, Fresno, California

Winter is the perfect time to visit this national park. Not only will you catch more wildlife and fewer crowds, but the magic of Yosemite comes alive in winter. 

A freshly fallen layer of snow over the towering sequoias and pines makes winter in Yosemite National Park a different outdoor experience altogether. You’ll find yourself gazing out over the park with new eyes and a new appreciation for the snow seeping through your favorite pair of winter socks.

Breckenridge via Denver, Colorado

This mountain town at the base of the Rocky Mountains’ Tenmile Range is another skiers’ paradise.

The mountains provide endless fun learning the ropes and shooting down the slopes at breakneck speed. And when not on the slopes, you can wander the same streets that once brought miners rushing west in search of gold.

Lake Tahoe, Nevada

Lake Tahoe is known for its year-round fun. While summer has its perks, winters on the lake are their own unique experience. After all, we are talking about the place that, on its California side, hosted the 1960 Winter Olympic games.

Head to North Lake Tahoe on the Nevada side for all kinds of fun winter activities. Go for nighttime ice skating, be the first to rise and head to the slopes, or relax and enjoy the heat of a spa amid the winter chill. Whatever your winter vacation desires, Lake Tahoe delivers.

Boston, Massachusetts

For a less adrenaline-pounding and more time-traveling winter destination, Boston awaits. 

Cobblestone streets covered in snow and charming colonial buildings sporting Christmas lights are just a few reasons this town makes a wonderful winter getaway. Ice skate on a local pond, wander the markets, and warm up with a cup of hot chocolate after a fun-filled day. 

Family Vacations

Planning a trip for the whole family can quickly get expensive and tedious, between finding the right flight, booking an affordable hotel, and securing a good deal with a car rental company. 

A Southwest Vacations package makes all of that planning just a little bit easier. Package deal options will have you taking your family on unique getaways to national parks, beachside resorts, and more. 

Orlando, Florida

Some might call this city the king of family vacations. Orlando is a bit of an expert on family fun, with enough theme parks to keep your family entertained for days. It’s no surprise that Southwest Vacations would be sure to include Orlando among its top Florida destinations. 

A rental car is a must in Orlando because once your family has their fill of theme parks, you can take a relaxing break and soak in the Florida sun as you’re meant to—laid back and toes in the sand on a gorgeous beach. 

Nashville, Tennessee

Everyone loves dinner and a show. Treating your family to both in the “Music City” itself is sure to go down as a hit. 

Hiking in beautiful state parks, discovering murals painted all over the city, and exploring Nashville’s iconic music scene are just a few of the activities you can get up to here.

A city with a voice of its own, Nashville’s siren call will have your family enchanted from the first song. 

Anaheim, California

For a west coast retreat, Anaheim delivers fun-packed amusement parks and rides that the whole family will enjoy. And outside of the whirlwind of your favorite movie-themed rides, Orange County is one car rental away. 

Thirty minutes takes you out of the midst of theme parks and right up to the mesmerizing Pacific coast, perfect for lazy days on the beach, surfing the waves, and enjoying Anaheim’s picture-perfect weather.

Puerto Vallarta, Mexico

As a hot tropical getaway for vacationers with kids, Puerto Vallarta is much-loved for its Southwest Vacation package and frequent deals to travel.

Have fun on the beach or experience some thrills in the water park, and snorkel in beautiful blue-green waters surrounding uninhabited islands. 

It won’t take long before the whole family falls in love with Puerto Vallarta.

Nassau, Bahamas

The Bahamas are a Caribbean gem, with fantastic food, stunning beaches, and one of the largest barrier reefs in the world.

For a destination as special as the Bahamas, Southwest Vacations offers all-inclusive deal options to take your family vacation to the next level. If you’re looking for a family getaway with no cooking, no cleaning, and no worries, then Nassau is the place for you.

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