Southwest Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Top Southwest Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Cove Hotel St.Croix

The Cove Hotel St.Croix

3 out of 5
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Christiansted (STX)
10/10 Exceptional! (34 reviews)
From the moment we arrived, we knew we had found something special. The owners welcomed us with warm smiles and genuine hospitality that made us feel at home instantly. Our room was spotless, beautifully decorated, and offered breathtaking views of the turquoise Caribbean Sea. The amenities were top-notch—comfortable beds, a sparkling pool, and close to the beach. What stood out the most was the owner’s attention to detail. From remembering our names to offering personalized recommendations for exploring the island, they truly went above and beyond. This hotel was the perfect base for our St. Croix adventure, combining comfort, beauty, and authentic island charm. We can’t wait to come back!

Reviewed on Jul. 30, 2025

Gorgeous Ocean Views! Welcome to Bella Breeze! BeachFront 2BR 2BA

Gorgeous Ocean Views! Welcome to Bella Breeze! BeachFront 2BR 2BA

4 out of 5
per person
Sep 12 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Christiansted (STX)
8.8/10 Excellent! (8 reviews)
The apartment needs a deeper cleaning. Certain areas have dust and spiderwebs, and the kitchen requires attention. The central air conditioning does not cool the master bedroom well. The curtains in the master bedroom should be replaced to block out the sunlight, too much light comes through the glass windows. The mattresses in the second bedroom are very uncomfortable.

Reviewed on Jul. 28, 2025

Oceans at Divi Carina Bay Adults Only

Oceans at Divi Carina Bay Adults Only

4 out of 5
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Christiansted (STX)
7.8/10 Good! (195 reviews)
Very friendly staff. Too much seaweed. Quiet and comfortable. Bartenders are great! But if you really want to enjoy the beach go somewhere else. Taxi rates are really high. Rent a car. Food is good but very low choices.

Reviewed on Jun. 3, 2025

Divi Carina Bay All Inclusive Beach Resort & Casino

Divi Carina Bay All Inclusive Beach Resort & Casino

3.5 out of 5
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Christiansted (STX)
8/10 Very Good! (459 reviews)
I wish there had been more seafood options available.

Reviewed on Jul. 31, 2025

The Frederiksted Hotel

The Frederiksted Hotel

3 out of 5
Downtown Frederiksted
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Christiansted (STX)
8.4/10 Very Good! (293 reviews)
The Frederiksted hotel was clean. The bed was comfortable. The room was nice. I enjoyed my stay there.

Reviewed on Jun. 1, 2025

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 CA $318 per night from Aug 3 to Aug 4
CA $318
CA $358 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (870 reviews)
"Third time….amazing every single time!!"

Reviewed on Jul. 29, 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! (283 reviews)
"Our stay at Cottages By The Sea was absolutely amazing! This quaint little complex is a crown jewel of St. Croix. The staff was very friendly and it is a very calm and relaxing environment with pristine beach access. We stayed in the Crow's nest in which our second level porch overlooking the sea ..."

Reviewed on Jul. 28, 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 Apr. 2, 2025

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PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"
See all 913 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.
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Frequently asked questions

How much does a Southwest vacation package cost?
Maybe less than you imagined — from a tempting CA $1,483, 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.