Southwest Holidays

Book a Hotel + Flight or Car together to unlock savings

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 6.698.595 ₫ per night from 25 Jul to 26 Jul
6.698.595 ₫
7.535.920 ₫ total
25 Jul - 26 Jul
includes taxes & fees
9.4/10 Exceptional! (982 reviews)
"This is a unique property with a lovely access to the best beach ever! The staff is friendly and knowledgeable. The room is spacious and all utilities worked perfectly. I loved that it is non frills and at the same time well thought out in terms of comfort. Will certainly recommend and return!"

Reviewed on 10 Jul 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! (323 reviews)
"By far the best beach on the island. The property has everything you need. Cute. Modest. Steps from the beach. Perfect for a short term or long term stay! I would not hesitate to recommend to my friends and family, or book again! Cottages by the Sea is my new Happy Place!!!!!"

Reviewed on 6 Jul 2026

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Cottages by the Sea
Carina Bay Boutique All Inclusive Resort & Casino

Carina Bay Boutique All Inclusive Resort & Casino

3.5 out of 5
5025 Turner Hole Christiansted St. Croix
7.6/10 Good! (733 reviews)
"Where do I start the place is dated and not maintained well. Seaweed was bad which is not there fault but it smelt of sulfur. The bees were awful at the bar. Food was a buffet style that was not that great. Coffee shop had no espresso machine. It is in the middle of nowhere and you must taxi which ..."

Reviewed on 12 Jul 2026

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Carina Bay Boutique All Inclusive Resort & Casino
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 1null000null000 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)
Find out about the history of Estate Two Brothers with a stop at Fort Frederik. Amble around this relaxing area's beautiful beaches or seek out the snorkelling spots.
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