Deals on vacations and trips to Southwest

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Southwest flight + hotel vacation packages

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

King Christian Hotel

3.5 out of 5
Christiansted Historic District
Price was $953, price is now $760 per person
$760
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Christiansted (STX)
This smoke-free hotel's 3 restaurants, 4 bars/lounges, and outdoor pool are some of the featured amenities. WiFi in public areas is free. Self parking, a coffee shop, and a terrace are also offered.
Carina Bay Boutique All Inclusive Resort & Casino

Carina Bay Boutique All Inclusive Resort & Casino

3.5 out of 5
Save 100% on your flight
Price was $1,999, price is now $1,266 per person
$1,266
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and free self parking.
Oceans at Divi Carina Bay Adults Only

Oceans at Divi Carina Bay Adults Only

4 out of 5
Save 100% on your flight
Price was $2,213, price is now $1,424 per person
$1,424
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Christiansted (STX)
A casino, 3 restaurants, and 2 outdoor pools are all featured at this all-inclusive hotel. Dine at the beachfront restaurant and relax with beach umbrellas. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and free self parking.
The Cove Hotel St.Croix

The Cove Hotel St.Croix

3 out of 5
Price was $1,034, price is now $795 per person
$795
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Christiansted (STX)
An outdoor pool, free self parking, and concierge services are featured at this hotel. WiFi in public areas is free. Dry cleaning and luggage storage are also provided.
The Frederiksted Hotel

The Frederiksted Hotel

3 out of 5
Downtown Frederiksted
Price was $1,430, price is now $1,140 per person
$1,140
per person
Oct 18 - Oct 25
found 24 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.

Top Southwest hotels 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
$230 nightly
The price is $258 total per night
$258 total
Aug 30 - Aug 31
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.
Pool
Breakfast included
Cottages by the Sea

Cottages by the Sea

3 out of 5
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.
Parking included
Free WiFi
PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"

PARADISE COVE SECLUDED PRISTINE VILLA, "MARGARITA"

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An outdoor pool is featured at this vacation home, along with a garden and laundry facilities.
Pool
Kitchen
Carambola Beach Resort St. Croix, US Virgin Islands

Carambola Beach Resort St. Croix, US Virgin Islands

4 out of 5
Estate Davis Bay, Kingshill, St. Croix
Free Cancellation
Reserve now, pay when you stay
$232 nightly
The price is $261 total per night
$261 total
Sep 3 - Sep 4
Total with taxes and fees
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 4 conference rooms, free WiFi in public areas, and laundry service. Relax with a drink at the poolside bar and enjoy perks like free self parking.
Pool
Parking included
The Buccaneer Beach & Golf Resort

The Buccaneer Beach & Golf Resort

4 out of 5
Estate Shoys, Christiansted, St. Croix
Free Cancellation
Reserve now, pay when you stay
$250 nightly
The price is $276 total per night
$276 total
Sep 17 - Sep 18
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.
Pool
Breakfast included
Carina Bay Boutique All Inclusive Resort & Casino

Carina Bay Boutique All Inclusive Resort & Casino

3.5 out of 5
5025 Turner Hole, Christiansted, St. Croix
Get rates
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. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and free self parking.
Pool
Breakfast included
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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.

Photos of local treasures

Browse Southwest vacation photos for more inspiration

Whim Plantation Museum
Whim Plantation Museum
Whim Plantation Museum showing heritage elements
Whim Plantation Museum featuring heritage elements and flowers
Whim Plantation Museum showing interior views and heritage elements

Frequently asked questions

How much are vacation packages to Southwest?
Packages, which include hotels and flights in Southwest, start from as little as $760. 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.