Southwest Vacation Packages 2026 from $909

Southwest flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Waves at Cane Bay

$909

per person

May 28 - May 31

found 8 hours ago

Roundtrip non-stop flight included

Baltimore (BWI) to Christiansted (STX)

This hotel features a restaurant and 2 bars/lounges. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, express check-in, and express check-out are also on offer.

Carina Bay Boutique All Inclusive Resort & Casino

$972

per person

May 28 - May 31

found 8 hours ago

Roundtrip non-stop flight included

Baltimore (BWI) to Christiansted (STX)

A casino, 2 restaurants, and 2 outdoor pools are all featured at this all-inclusive hotel. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.

The Frederiksted Hotel

Downtown Frederiksted

$1,076

per person

Jun 4 - Jun 7

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Christiansted (STX)

A rooftop terrace, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.

Colony Cove Beach Resort by Antilles Resorts

$1,167

per person

Jun 21 - Jun 25

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Christiansted (STX)

An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.

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

$1,216

per person

Jun 21 - Jun 25

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Christiansted (STX)

An outdoor pool, free self parking, and barbecue grills are featured at this condo. A terrace, a garden, and a picnic area are also on offer.

Top Southwest hotels deals

Sand Castle on the Beach - Adults Only

127 Smithfield Frederiksted St. Croix

$244 nightly

$275 total

Apr 4 - Apr 5

Total with taxes and fees

This hotel features 2 outdoor pools, a restaurant, and a bar/lounge. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at the poolside bar and enjoy free perks like continental breakfast and free self parking.

Cottages by the Sea

127A Smithfield Rd Frederiksted St. Croix

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This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Enjoy a day at the beach snorkeling, or relax with beach umbrellas. A terrace, a garden, and a library are also on offer.

PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"

Frederiksted, St. Croix St. Croix Island

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An outdoor pool is featured at this vacation home, along with a garden and laundry facilities.

Carina Bay Boutique All Inclusive Resort & Casino

5025 Turner Hole Christiansted St. Croix

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Palms Resort and Beach

4126 La Grande Princess Christiansted St. Croix

$114 nightly

$127 total

Apr 29 - Apr 30

Total with taxes and fees

This resort features an outdoor pool, an outdoor tennis court, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. There's a beach bar on site, and laundry facilities and wedding services are also provided.

The Buccaneer Beach & Golf Resort

Estate Shoys Christiansted St. Croix

Free Cancellation

Reserve now, pay when you stay

$381 nightly

$422 total

Apr 29 - Apr 30

Total with taxes and fees

A golf course, 3 restaurants, and 2 outdoor pools are all featured at this boutique hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families will appreciate the free kid's club, onsite laundry facilities, and in-room childcare.

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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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Trunk bay on St John island, US Virgin Islands

Frequently asked questions

How much are vacation packages to Southwest?

Packages, which include hotels and flights in Southwest, start from as little as $909. Make your daydreams a reality and begin your booking with Travelocity today.

Where can I get the best vacation package deals for Southwest?

Travelocity is the only place you need to go to score a great Southwest package deal. Take your pick of 400 airlines and 1,000,000 properties around the world and put together a travel itinerary that's right for you. With almost endless choice, you have inspiration galore for your next big adventure.

Why should I purchase my Southwest vacation package with Travelocity?

Whether you're searching for the ultimate unplugged escape or after the fun and excitement that only a big city can provide, booking everything with Travelocity saves you time, hassle and money. No need to scour through countless websites to find the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our professional customer service experts are available for you round-the-clock.

Can I save money on my Southwest car rental if I combine it with my hotel or flight?

Sure can. And our Southwest vacation packages will help you do it. With just a few clicks you can save cash as well as time by booking everything in one place. Pick up the keys to your rental car then chart your own course. Searching for things to do? Add some tours or experiences to your package and save on those too.

Which airport is best for Southwest?

Cyril E. King Airport (STT), Terrance B. Lettsome Intl. Airport (EIS) and Antonio Rivera Rodriguez Airport (VQS) are the most used airports for those flying in and out of Southwest.