Southwest Vacations & Trips

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 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

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 ₩302,076 per night from Sep 15 to Sep 16
₩302,076
₩339,836 total
Sep 15 - Sep 16
includes taxes & fees
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
Get rates
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
Fully refundableReserve now, pay when you stay
The price is ₩294,968 per night from Sep 18 to Sep 19
₩294,968
₩331,839 total
Sep 18 - Sep 19
includes taxes & fees
Carambola Beach Resort St. Croix, US Virgin Islands
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 vacation 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 vacation?
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 vacation!
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 vacation is only a few clicks away.
Can I choose my airline with a Southwest Expedia vacation 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 vacation package?
It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Southwest vacation 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.