Southwest Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Southwest Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Tamarind Reef Resort Spa & Marina
CA $1,835
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Christiansted (STX)
8.2/10 Very good! (604 reviews)
Flight from Miami was delayed because of thunderstorms, called hotel to let them know, no answer.... Called many times, left messages and phone numbers, no call back, nothing. Finally got to St. Croix and went straight to the hotel, exhausted, ready for shower and bed, long day, got there at 3AM. Nobody around, AT ALL!!!!! Had to sleep in the rental car until 7AM. ABSOLUTELY TERRIBLE!!! Will never go there again and will never, ever recommend. Worst in my entire life and I travel all over.
Reviewed on Aug 30, 2026
Carina Bay All Inclusive Resort & Casino - Adults Only
CA $3,667
per person
Nov 12 - Nov 22
found 10 hours ago
Roundtrip flight included
Calgary (YYC) to Christiansted (STX)
7.4/10 Good! (760 reviews)
We brought our entire family on vacation a group of 10. An all-inclusive resort was really the only financial option for this large of a party. After experiencing this disgusting Motel 6 like place, we should have rented a home and purchased local food and enjoyed the local nightlife! there was zero entertainment, unusable beach, no amenities or anyone working the activity “center “, terrible food, limited bar hours and we felt to always inconvenience the staff by being there ! we had to spend more money renting a car and leaving the resort eating at local restaurants and enjoying other beaches! If you can find a very cheap daily rate, this would be a good place to just sleep and go enjoy the island, but beware of the overpowering seaweed smell- NEVER got cleaned up or goes away. The turtles were NOT NESTING on this beach. Everything is run down and never cleaned(vomit and iguana poop -pool side and wasn’t cleaned up the entire six days we were there) the Divi website is very misleading about this location. Yes I have buyers remorse!
Reviewed on Sep 9, 2026
Grapetree Bay Hotel & Villas
Grapetree
CA $2,713
per person
Nov 12 - Nov 22
found 10 hours ago
Roundtrip flight included
Calgary (YYC) to Christiansted (STX)
8.8/10 Excellent! (209 reviews)
We had an amazing stay at Grapetree Bay. The rooms are as pictured clean, renovated and large. AC was nice and cold. The staff was very friendly and professional. Enjoyed all our delicious meals on the balcony with a beautiful view of the ocean. I would recommend this property to everyone and cannot wait to return.
Reviewed on Aug 28, 2026
Southwest Hotel Deals
Sand Castle on the Beach - Adults Only
127 Smithfield Frederiksted St. Croix
CA $299
CA $336 total
Sep 11 - Sep 12
includes taxes & fees
PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"
Frederiksted, St. Croix St. Croix Island
9.8/10 Exceptional! (53 reviews)
"It was excellent and will stay again."
Reviewed on Aug 11, 2026
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 CA $1,835, 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.
Stay near popular Southwest attractions
Fort Frederik
8.2/10 (204 reviews)
Once an important defensive stronghold, this atmospheric fort now houses a museum dedicated to the island’s enthralling history.
Estate Whim Museum
8.6/10 (43 reviews)
Explore this serene, tropical plantation and imagine what life was like here in the days when sugar cane production thrived in the Caribbean.
Carambola Golf Club
8.4/10 (25 reviews)
Play a round of golf at Carambola Golf Club and enjoy other activities in Estate Whim such as snorkeling. Wander the beautiful beaches and seaside in this relaxing area.
Carlton Beach
8.8/10 (8 reviews)
Why not spend a lazy afternoon at Carlton Beach during your trip to Frederiksted? Wander the beautiful beaches in this romantic area.
Caribbean Museum Center for the Arts
Enjoy an outing to Caribbean Museum Center for the Arts during your stay in Estate Two Brothers.
Carmbola Tide Pools
8.6/10 (40 reviews)
Enjoy a trip to Carmbola Tide Pools and popular activities like snorkeling in Estate Whim. Wander the beautiful beaches and seaside in this relaxing area.
Old Danish School
7.8/10 (23 reviews)
You can learn about the history of Estate Two Brothers with a trip to Old Danish School. Wander the beautiful beaches and seaside in this relaxing area.
St. Patrick's Catholic Church
8.4/10 (38 reviews)
St. Patrick's Catholic Church is just one of the places to see in Estate Two Brothers, so why not enjoy the other things to explore during your travels? Stroll along the seaside in this relaxing area, or seek out the snorkeling spots.
What to do in Southwest
Island Chocolate Experience with Tasting
CA $87
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
