Southwest Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Southwest Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Ambros Daytona, Trademark Collection by Wyndham
$605
per person
Dec 17 - Dec 21
found 5 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Orlando (MCO)
Book a stay at this beach hotel in Daytona Beach Shores. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Beach at Daytona Beach and Daytona Beach Boardwalk are located nearby.
Disney's Animal Kingdom Lodge
Bay Lake
$1,388
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Orlando (MCO)
Book a stay at this luxury hotel in Kissimmee. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
$818
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
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
Captiva Beach Resort
South Village
$1,137
per person
Nov 9 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Tampa (TPA)
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Everything
Reviewed on Sep 30, 2026
Siesta Palms By the Beach
South Village
$1,297
per person
Nov 9 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Tampa (TPA)
Stay at this hotel in Siesta Key. Enjoy free WiFi, free parking, and a garden. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
The unit was very clean. We had everything we needed to enjoy the beach. Would definitely stay there again. Loved the Breeze Trolley to all shops and restaurants. The pool was very clean and nice. It was very quiet while we were there.
Reviewed on Sep 23, 2026
The Westin Sarasota
Central Sarasota
$1,498
per person
Nov 9 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Tampa (TPA)
Book a stay at this spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.
There was a water leak in front of the window
Reviewed on Sep 30, 2026
Top Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Legoland Florida Hotel
1 Legoland Way Winter Haven FL
Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions LEGOLAND® Florida and Peppa Pig Theme Park Florida ...
Days Inn & Suites by Wyndham Lakeland
4502 N Socrum Loop Rd Lakeland FL
Book a stay at this business-friendly hotel in Lakeland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Howard Johnson by Wyndham Lakeland
939 W. Robson St. Lakeland FL
Book a stay at this business-friendly hotel in Lakeland. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Comfort Inn & Suites Lakeland North I-4
3520 N Hwy 98 Lakeland FL
Book a stay at this business-friendly hotel in Lakeland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Best Western Plus Winter Haven Inn & Suites
5801 Roosevelt Dr Winter Haven FL
Book a stay at this business-friendly hotel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Lakeland Center
525 W Orange St Lakeland FL
Book a stay at this business-friendly hotel in Lakeland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Hampton Inn by Hilton Plant City
2702 Thonotosassa Rd Plant City FL
Stay at this hotel in Plant City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Howard Johnson by Wyndham Winter Haven FL
1300 3rd St Winter Haven FL
Stay at this motel in Winter Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Staybridge Suites Winter Haven Auburndale by IHG
305 5th St NW and Avenue D NW Winter Haven FL
Stay at this hotel in Winter Haven. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
Extended Stay America Premier Suites Lakeland I4
4360 Lakeland Park Drive Lakeland FL
Book a stay at this business-friendly hotel in Lakeland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
SpringHill Suites by Marriott Lakeland
511 WEST LIME ST Lakeland FL
Book a stay at this business-friendly hotel in Lakeland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Lakeland East
4315 Lakeland Park Dr Lakeland FL
Book a stay at this business-friendly hotel in Lakeland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Birch Hill Suites - Lakeland
4335 Williamstown Boulevard Lakeland FL
Stay at this hotel in Lakeland. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Shoppes of Lakeland and Lakeland Square Mall are located ...
Motel 6 Lakeland, FL
3120 US 98 North Lakeland FL
Stay at this motel in Lakeland. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
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.
Best points of interest in Lakeland
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