Southwest Holidays & Package Deals 2026

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Southwest Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Henry E. Rohlsen Airport (STX)

Our pick of the best Southwest Hotel Deals

Sand Castle on the Beach - Adults Only

127 Smithfield Frederiksted St. Croix

AU$349

8 Oct - 9 Oct

includes taxes & fees

Cottages by the Sea

127A Smithfield Rd Frederiksted St. Croix

9.6/10 Exceptional! (331 reviews)

"Would stay again and definitely recommend best view on the island"

Reviewed on 26 Sept 2026

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Carina Bay All Inclusive Resort & Casino - Adults Only

5025 Turner Hole Christiansted St. Croix

7.4/10 Good! (786 reviews)

"Everything was great."

Reviewed on 5 Oct 2026

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See all 915 properties in Southwest

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.

Frequently asked questions

How much does a Southwest holiday package cost?

Maybe less than you imagined — from a tempting , actually! By combining flights, hotels and car rentals into a custom-built package, your Southwest escape is just a few clicks away.

How do I get a cheap travel package to Southwest?

You'll save loads of cash if you bundle your hotels, car rentals and flights into a Southwest travel package. Sometimes cheap means fewer options. But not with Expedia. We offer over 550 partner airlines and 1 000 000 properties across the globe, so you'll always have plenty of variety to choose from. Like to save even more? Add some interesting activities to your package deal to unlock even bigger bargains! After all, travel is about more than just getting to your destination.

How far in advance should I book my Southwest holiday?

Reward yourself with the biggest variety and the lowest prices by booking your trip to Southwest early. Air carriers typically publish flights anywhere up to 12 months before departure, so secure your spot as soon as possible. Having said that, Expedia is committed to giving you the best bargains around, so there's never a bad time to book your dream holiday!

What does an Expedia Southwest travel package include?

Hotels, flights and a reliable car for your road trip adventures. Simply pick and choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of activities and tours and watch your savings grow. When it comes to creating your Southwest escape, you're in charge!

What should I know before booking a Southwest travel package?

You can save big by combining your airfares, hotels and rental cars. Once you've created your package, you can add on things like activities or tours. Your next unforgettable holiday is only a few clicks away.

Can I choose my airline with a Southwest Expedia holiday package?

Definitely. Expedia has over 550 partner airlines to select from all over the world. With all that choice at your fingertips, finding the ideal carrier to take you to Southwest will be a cinch.

If I'm not able to travel, can I cancel my Southwest holiday package?

It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Southwest holiday package. If your booking was made in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to find out more.

Stay near popular Southwest attractions

A red colonial building with arched doorways and a central archway, labeled "1760".

Fort Frederik

8.2/10 (204 reviews)

Once an important defensive stronghold, this atmospheric fort now houses a museum dedicated to the island’s enthralling history.

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A stone building with green shutters and a sign that reads "Welcome to the Museum Store."

Estate Whim Museum

8.6/10 (43 reviews)

Explore this serene, tropical plantation and imagine what life was like here in the days when sugar cane production thrived in the Caribbean.

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Carambola Golf Club

8.4/10 (25 reviews)

Play a round of golf at Carambola Golf Club and enjoy other activities in Estate Whim such as snorkelling. Wander through the beautiful beaches and seaside in this relaxing area.

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Carlton Beach

8.8/10 (8 reviews)

Why not spend a lazy afternoon at Carlton Beach during your trip to Frederiksted? Wander the beautiful beaches in this romantic area.

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Old Danish School

7.8/10 (23 reviews)

You can learn about the history of Estate Two Brothers when you stop by Old Danish School. Wander through the beautiful beaches and seaside in this relaxing area.

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St. Patrick's Catholic Church

8.4/10 (38 reviews)

St. Patrick's Catholic Church is just one of the places to see in Estate Two Brothers, so why not enjoy the other things to explore during your travels? Stroll along the seaside in this relaxing area or seek out the snorkelling spots.

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Carmbola Tide Pools

8.6/10 (40 reviews)

Enjoy a trip to Carmbola Tide Pools and popular activities such as snorkelling in Estate Whim. Wander through the beautiful beaches and seaside in this relaxing area.

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