On Top of The World Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest On Top of The World Vacation Packages
- Saddlebrook Resort
Oct 10 - Oct 15Saddlebrook Resort + Flight
Wesley Chapel South5 nights4.0 star property8.0/10 - Very good (143 reviews)Roundtrip • Toronto (YTO) - Tampa (TPA)YYZ - TPA • 1 stop TPA - YYZ • 1 stopCA $1,229CA $887found 8 hours agoper traveller - The Avalon Club
Oct 10 - Oct 15The Avalon Club + Flight
Clearwater Beach5 nights4.0 star property9.4/10 - Exceptional (574 reviews)Roundtrip • Toronto (YTO) - Tampa (TPA)YYZ - TPA • 1 stop TPA - YYZ • 1 stopCA $2,770CA $1,770found 11 hours agoper traveller - CW Hotel
Oct 10 - Oct 15CW Hotel + Flight
Clearwater Beach5 nights4.0 star property9.6/10 - Exceptional (30 reviews)"We were on the 7th floor in a suite with a wrap around balcony and we could see the bay and the ocean. It was a easy 5 min walk to the Clearwater beach. Great location, great room and good food at the hotel. We will definitely be coming back."Reviewed July 27, 2026Roundtrip • Toronto (YTO) - Tampa (TPA)YYZ - TPA • 1 stop TPA - YYZ • 1 stopCA $1,632CA $1,120found 11 hours agoper traveller - Wyndham Grand Clearwater Beach
Aug 27 - Aug 31Wyndham Grand Clearwater Beach + Flight
Clearwater Beach4 nights4.0 star property9.4/10 - Exceptional (3,616 reviews)"Room was clean. Staff was excellent. Location was great. Would stay again."Reviewed July 27, 2026Roundtrip • Toronto (YYZ) - Tampa (TPA)YYZ - TPA • 1 stop TPA - YYZ • 1 stopCA $1,637CA $1,136found 9 hours agoper traveller - Cedar Cove Resort and Cottages
Sept 24 - Sept 27Cedar Cove Resort and Cottages + Flight
Holmes Beach3 nights3.0 star property9.2/10 - Wonderful (563 reviews)"Everything was amazing from the moment I walked in to the office for check in, the staff was friendly, helpful and informative! This was a home away from home! I will definitely be back next year!"Reviewed July 26, 2026Roundtrip • Toronto (YYZ) - Tampa (TPA)YYZ - TPA • 1 stop TPA - YYZ • 1 stopCA $1,544CA $1,098found 1 day agoper traveller
On Top of The World Hotel Deals
Holiday Inn Express Hotel & Suites Clearwater/Us 19 N by IHG
Holiday Inn Express Hotel & Suites Clearwater/Us 19 N by IHG
La Quinta Inn by Wyndham Clearwater Central
La Quinta Inn by Wyndham Clearwater Central
Comfort Suites Clearwater - Dunedin
Comfort Suites Clearwater - Dunedin
Clarion Inn & Suites Central Clearwater Beach
Clarion Inn & Suites Central Clearwater Beach
Best Western Plus Yacht Harbor Inn
Best Western Plus Yacht Harbor Inn
Residence Inn by Marriott Clearwater Downtown
Residence Inn by Marriott Clearwater Downtown
Hampton Inn & Suites Tampa Northwest/Oldsmar
Hampton Inn & Suites Tampa Northwest/Oldsmar
The Grant Street Inn Dunedin Downtown Historic District, an Ascend Collection Hotel
The Grant Street Inn Dunedin Downtown Historic District, an Ascend Collection HotelFrequently Asked Questions
How much does an On Top of The World vacation package cost?
Maybe less than you imagined — from just CA $887, actually! By combining hotels, flights and car rentals into a customized vacation package, your trip to On Top of The World is only clicks away.
How do I get a cheap travel package to On Top of The World?
Our On Top of The World vacation packages mean plenty of savings for the savvy globetrotter. For the best deal, simply bundle your hotel, flights and extras (including tours) into a budget-friendly package. But low prices are just the beginning of your next awesome adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotels around the world to pick from. Whatever your budget or style, there's a package with your name on it.
Where should I stay in On Top of The World?
Stay where the action is. Many travelers book hotels around top attractions, like Ruth Eckerd Hall, Eddie C. Moore Softball Complex and Westfield Countryside Mall.
How far in advance should I book my On Top of The World vacation?
You'll be rewarded with the widest variety and the cheapest prices by booking your trip to On Top of The World early. Air carriers usually release flight tickets anywhere up to a year prior to departure, so reserve your spot as soon as you can. That said, Expedia is committed to providing you with the best bargains around, so it's always a good time to book your dream vacation!
What does an Expedia On Top of The World travel package include?
Expedia has all you need to plan your On Top of The World trip, but what your package looks like is your call. Choose from a combination of flights, rental cars and hotels. Looking for some activities to keep you on the move? Once you've made your booking, you can add them too. No matter your style, there's a package deal to meet your needs.
What should I know before booking an On Top of The World travel package?
You'll enjoy big savings when you combine your flights, hotels and rental cars into a travel package. Not only that, booking everything in one place will make your trip planning easier. So why waste your money or time? Whether you're organizing a ritzy city getaway or a budget solo adventure, have a look at our package deals today.
Can I choose my airline with an On Top of The World Expedia vacation package?
You certainly can. We offer more than 550 airline partners all over the world, so fly with the carrier that best suits your budget needs.
If I'm not able to travel, can I cancel my On Top of The World vacation package?
Because we know life can be unpredictable, the answer is yes. For more information, visit our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to change or cancel it with no penalties. Your airline, hotel or car rental company may impose a fee if your booking is older than that.