Southwest Vacation Packages
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Top Holiday Package Deals in Southwest
Price found within the past 48 hours. Click for updated prices.
CW Hotel
CA $1,191
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (48 reviews)
Great place to stay in Clearwater Beach. The staff is very communicative and responsive. There are a few discrepancies on the property rules and regulations but of you fine the details you will be prepared. For example the website stated that the incidental hold is for $200 but is actually for $300 once you are checking in.
Reviewed on Aug 15, 2026
Where to stay in Southwest
Find the best Southwest areas and neighborhoods for the activities you enjoy most. Learn more about Southwest
Downtown Lakeland
2 out of top 10 points of interest in this area
If you're spending some time in Downtown Lakeland, RP Funding Center and Lake Mirror are top sights worth seeing.
Lake Hollingsworth
If you're spending some time in Lake Hollingsworth, Lake Hollingsworth and Veterans Park are top sights worth seeing.
Lakeland Highlands
When in Lakeland Highlands, you can plan a visit to Family Fun Center and The Club at Eaglebrooke, some noteworthy sights in the nearby area.
South Lake Morton
1 out of top 10 points of interest in this area
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 RP Funding Center.
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 Theatre.
Southwest Hotel Deals
Beachy getaway in lovely Lakeland, Fl!
Lakeland FL
9.8/10 Exceptional! (9 reviews)
"House was very clean had all the essentials needed for staying, host was great with communication. Very family friendly home with a beautiful backyard and pool, and nice game room for kids to be entertained"
Reviewed on Jul 6, 2026
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundableReserve now, pay when you stay
CA $121
CA $136 total
Sep 13 - Sep 14
includes taxes & fees
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
CA $256
CA $286 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (179 reviews)
"Great customer service!"
Reviewed on Aug 9, 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.
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.