Southwest Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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$425 per night from 15 Aug to 16 Aug
NZ$425
15 Aug - 16 Aug
includes taxes & fees
9.2/10 Wonderful! (873 reviews)
"We loved this place so much. Peaceful, beautiful, great staff. Would stay here again."

Reviewed on 10 Aug. 2025

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
9.4/10 Exceptional! (285 reviews)
"Everything was absolutely perfect and beautiful here! Very quiet and peaceful and relaxing. Perfect for a couples getaway or a quiet beach vacation with your kids!"

Reviewed on 4 Aug. 2025

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

PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"

Frederiksted, St. Croix
9.6/10 Exceptional! (43 reviews)
Wonderful Spring Break
"I couldn’t be more pleased with the stay. Great location, house was perfect, Gail responded promptly to a few questions."

Reviewed on 2 Apr. 2025

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PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"
See all 914 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.