Southwest Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Our pick of the best Southwest Hotel Deals

Sand Castle on the Beach - Adults Only

Sand Castle on the Beach - Adults Only

3.5 out of 5
127 Smithfield Frederiksted St. Croix
The price is NZ$502 per night from 11 July to 12 July
NZ$502
11 July - 12 July
includes taxes & fees
9.4/10 Exceptional! (979 reviews)
"Great staff, good food"

Reviewed on 30 June 2026

Sand Castle on the Beach - Adults Only
Cottages by the Sea

Cottages by the Sea

3 out of 5
127A Smithfield Rd Frederiksted St. Croix
9.6/10 Exceptional! (322 reviews)
"The kitchen was well stocked, and the ocean was just steps away! Perfect room"

Reviewed on 14 June 2026

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Cottages by the Sea
PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"

PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"

Frederiksted, St. Croix St. Croix Island
9.8/10 Exceptional! (49 reviews)
"Such an amazing property! It was absolutely lovely. We did struggle to find the location, but after we found it for the first time, it was not a problem. The island was amazing and it was the perfect mother/daughter trip. Thank you so much!"

Reviewed on 7 Apr 2026

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PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"
See all 910 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 cruise ship docked at a pier with a red wall and cannons in the foreground.

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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What to do in Southwest

Parasail Experience in St Croix

Parasail Experience in St Croix

NZ$143
per adult
80% of travellers recommend
Parasail Experience in St Croix
Sea Turtle Snorkel Tour

Sea Turtle Snorkel Tour

NZ$100
per adult
Sea Turtle Snorkel Tour
Driving in the Left Lane: Self-Guided St. Croix Driving Tour

St. Croix’s Forts, Freedom, and Beaches: A Self-Drive Audio Tour

NZ$42
per traveller
St. Croix’s Forts, Freedom, and Beaches: A Self-Drive Audio Tour
See all activities in Southwest