Southwest Vacation Packages

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  • Better together

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

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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
Price was CA $1,606, price is now CA $1,308 per person
CA $1,308
per person
Jul 6 - Jul 11
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Christiansted (STX)
9.8/10 Exceptional! (179 reviews)
Enjoyed our stay at The Cove! The property is currently undergoing renovations. What has been completed LOOKS GREAT. Our room was very clean but unfinished. Room definitely needs more lighting and storage. No TV service, even after getting assistance to get online. AC unit in the room, unfortunately the last night, failed. Ample parking, and the grounds/pool area all are well taken care of and maintained. The staff/owners were the best! Any issues we had they were right there to help. The Cove, minus the minor issues, is a "diamond in the ruff", and would definitely consider rebooking another stay.

Reviewed on Apr 9, 2026

Carina Bay Boutique All Inclusive Resort & Casino

Carina Bay Boutique All Inclusive Resort & Casino

3.5 out of 5
Price was CA $2,583, price is now CA $1,883 per person
CA $1,883
per person
Jul 6 - Jul 11
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Christiansted (STX)
7.6/10 Good! (631 reviews)
Staff was friendly. Bartenders were amazing

Reviewed on Apr 15, 2026

The Frederiksted Hotel

The Frederiksted Hotel

3 out of 5
Downtown Frederiksted
Price was CA $1,991, price is now CA $1,528 per person
CA $1,528
per person
Jun 10 - Jun 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Christiansted (STX)
8.4/10 Very Good! (354 reviews)
This place was immaculate. I had beautiful sunsets and friendly people. I had delicous creole breakfast every morning. Ate at Napoleon's and Top Deck. Their food was fresh and very tasty. Must have sunset on the pier!!!

Reviewed on Apr 14, 2026

Victoria House

Victoria House

3.5 out of 5
Downtown Frederiksted
Price was CA $1,798, price is now CA $1,423 per person
CA $1,423
per person
Jun 10 - Jun 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Christiansted (STX)
9.2/10 Wonderful! (127 reviews)
Nice room and staff.

Reviewed on Apr 4, 2026

The Fred - Adults Only

The Fred - Adults Only

3.5 out of 5
Downtown Frederiksted
Price was CA $1,790, price is now CA $1,420 per person
CA $1,420
per person
Jun 10 - Jun 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Christiansted (STX)
8.4/10 Very Good! (371 reviews)
Beautiful place! We were there in the off-season, and almost had it to ourselves. The pool and the hot tub are gorgeous, and I can't think of a bar that has a better view! There is some walking required to get dinner, as local restaurants are a few blocks away, and the Fred's kitchen doesn't serve in the evening. The beach is beautiful, but not very accessible, as there are rocks you have to get over, before you can swim.

Reviewed on Apr 18, 2026

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 $327 per night from Apr 26 to Apr 27
CA $327
CA $368 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (946 reviews)
The most relaxing vacation we've ever taken. Staff, food, rooms, pools, beach, and snorkeling were all exceptional. My wife swam with a sea turtle! Expect to pay island prices for dinner, but it is well worth it. We hadn't planned on it but we ate every dinner at their restaurant, just a couple of ...

Reviewed on Apr 16, 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! (317 reviews)
Staff was excellent Room was great

Reviewed on Apr 2, 2026

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Cottages by the Sea
PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"

PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"

Frederiksted, St. Croix St. Croix Island
9.8/10 Exceptional! (49 reviews)
Such an amazing property! It was absolutely lovely. We did struggle to find the location, but after we found it for the first time, it was not a problem. The island was amazing and it was the perfect mother/daughter trip. Thank you so much!

Reviewed on Apr 7, 2026

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PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"
See all 912 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 $1,308, 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.