Southwest Holidays

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    Save up to €185 when you book a flight and hotel together*

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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 €239 per night from 31 Oct to 1 Nov
€239
31 Oct - 1 Nov
includes taxes & fees
9.2/10 Wonderful! (888 reviews)
The room exceeded expectations. The pictures make it seem darker than it is. Very clean and perfectly stocked with pillows, towels, kitchenette items. I’m not sure if the restaurant is under the same management. The vibe was completely different from the restaurant staff. While no one was unpleasant, ...

Reviewed on 24 Oct 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! (302 reviews)
The staff was friendly and very accommodating to what was needed. Very clean room.

Reviewed on 14 Oct 2025

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Cottages by the Sea
4Br, 5Bath, 5 minutes to Beach AC Home

4Br, 5Bath, 5 minutes to Beach AC Home

Federiksted
9.8/10 Exceptional! (56 reviews)
Nice clean house with a lot of room for everyone. Host was very accommodating with early church in and late check out to match our flight schedule. Bonnie if you like dogs let her know so she can let her sweet pup brownie come out to play in the huge back yard.

Reviewed on 14 Aug 2025

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4Br, 5Bath, 5 minutes to Beach AC Home
See all 903 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.