Southwest Holidays

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    Better together
    Save up to S$134 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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    Plan, book, and manage your trip all in one place
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Southwest

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 S$372 per night from 29 Nov to 30 Nov
S$372
includes taxes & fees
29 Nov - 30 Nov
9.2/10 Wonderful! (787 reviews)
"Amazing!!!"

Reviewed on 19 Nov,2024

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! (252 reviews)
"Our cottage Castaways is a bit rustic but have all the basic things and is comfortable. They had some issues with water supply due to island wide outage, but it was fixed within a day. The beach is very beautiful, easy access and you can snorkel for hours right at the beach, lots of tropical fish, ..."

Reviewed on 4 Nov,2024

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Cottages by the Sea
Carambola Beach Resort St. Croix, US Virgin Islands
Carambola Beach Resort St. Croix, US Virgin Islands
4 out of 5
Estate Davis Bay, Kingshill, St. Croix
The price is S$265 per night from 7 Dec to 8 Dec
S$265
includes taxes & fees
7 Dec - 8 Dec
7.4/10 Good! (920 reviews)
"Gorgeous beach. Your own secret hideaway"

Reviewed on 1 Nov,2024

Carambola Beach Resort St. Croix, US Virgin Islands
See all 803 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.