Southwest Vacation Packages

Plan, book, travel with confidence
Better together
Save up to CA $4,200 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Southwest

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

Seasons Florida Resort

CA $908

per person

Dec 11 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Orlando (MCO)

9/10 Wonderful! (3,949 reviews)

El stand muy amable. Los cuartos limpios.

Reviewed on Oct 2, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

CA $1,495

per person

Dec 20 - Dec 27

found 1 day ago

Roundtrip flight included

Halifax (YHZ) to Orlando (MCO)

8.4/10 Very good! (7,160 reviews)

Westgate Vacation Villas Resort

CA $1,009

per person

Dec 3 - Dec 10

found 7 hours ago

Roundtrip non-stop flight included

Halifax (YHZ) to Orlando (MCO)

8.2/10 Very good! (2,074 reviews)

Great location, property was very clean, pools were amazing. enjoyed our week stay, highly recommend. staff was very friendly and helpful

Reviewed on Oct 1, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

CA $1,596

per person

Dec 18 - Dec 23

found 1 day ago

Roundtrip flight included

Halifax (YHZ) to Orlando (MCO)

9.2/10 Wonderful! (1,003 reviews)

We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms. The staff at the main building were so helpful with our packages and printing documents for us. Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort. Overall, a great selection and would start again!

Reviewed on Sep 25, 2026

Westgate Cocoa Beach Resort

Save 100% on your flight

CA $1,286

per person

Dec 8 - Dec 14

found 20 hours ago

Roundtrip flight included

Toronto (YTO) to Orlando (MCO)

8.6/10 Excellent! (565 reviews)

Where to stay in Southwest

Find the best Southwest areas and neighborhoods for the activities you enjoy most. Learn more about Southwest

A garden with a central fountain, surrounded by white columns and covered walkways.

Lake Hollingsworth

If you're spending some time in Lake Hollingsworth, Lake Hollingsworth and Beerman Family Tennis Center are top sights worth seeing.

A calm lake with lily pads, surrounded by a park with palm trees and buildings.

Downtown Lakeland

2 out of top 10 points of interest in this area

If you're spending some time in Downtown Lakeland, Polk Theatre and RP Funding Center are top sights worth seeing.

A circular fountain with a statue in the center, surrounded by palm trees and a building with a red roof in the background.

South Lake Morton

If you're looking for some top things to see and do in South Lake Morton and surrounding area, you can visit Lake Mirror and Polk Theatre.

A crocodile resting on a log near a body of water with greenery around.

Lakeland Highlands

When in Lakeland Highlands, you can plan a visit to The Club at Eaglebrooke and Family Fun Center, some noteworthy sights in the nearby area.

A wooden boardwalk by a lake with trees and a bench.

Dixieland

While there might not be top attractions in Dixieland, you can explore the larger area and discover places like RP Funding Center and Polk Museum of Art.

Southwest Hotel Deals

Charming Home Close to Downtown, Fully Renovated

Lakeland FL

10/10 Exceptional! (39 reviews)

"We had a wonderful stay. The home is simple, comfortable and tidy. We had everything we needed. The kitchen is well appointed and the living room provided ample space to relax and visit. The beds were comfortable and cozy with extra pillows. We enjoyed our time there."

Reviewed on Sep 26, 2026

Get rates

Beachy getaway in lovely Lakeland, Fl!

Lakeland FL

Get rates

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL

Fully refundable

CA $156

CA $175 total

Oct 5 - Oct 6

includes taxes & fees

See all 945 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.