On Top of The World Vacation Packages

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Top Holiday Package Deals in On Top of The World

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,041, price is now CA $591 per person
CA $591
per person
Nov 16 - Nov 22
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (59 reviews)
Close to downtown safety harbor, oldsmar and Clearwater, the perfect retreat being close to everything but not in the heart of it all.

Reviewed on May 12, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was CA $1,867, price is now CA $1,090 per person
CA $1,090
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
9.6/10 Exceptional! (618 reviews)
Amazing customer service

Reviewed on Sep. 5, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $1,546, price is now CA $918 per person
CA $918
per person
Oct 11 - Oct 15
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
9.2/10 Wonderful! (1,056 reviews)
The property was nice but there is no bar/restaurant on site like there used to be. Once I got to the property I had to pay well over $100 in "resort fees" and taxes. I am not sure what qualifies as a resort but I guess this was just to use the pool? I mean there really isnt anything else on site, except a couple fire pits i never saw lit and a sad few hole putt putt course I never saw anyone use so dont even know if there was equipment. But the parking was easy. I tried to call to the front desk using their phone one morning but no one answered. So I called the main number using my cell phone, but no one answered. Not sure what that was all about.

Reviewed on Sep. 5, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $1,491, price is now CA $906 per person
CA $906
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (446 reviews)
Place was very clean loved how large it was and was in a great location, could walk to everything The only negative thing was the pool seemed to be pictured different on the website and was very small and the rooftop bar really cannot be called a bar. They were out of most of the beers didn’t sell liquor and really was not a bar at all.

Reviewed on Sep. 1, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was CA $1,955, price is now CA $1,207 per person
CA $1,207
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
9.2/10 Wonderful! (1,017 reviews)
Loved it Voco hotel was great clean and quiet great place to just sit back and relax place was not busy at all kids are all back in school thank god . Beach’s all near by 10 to 20 minute drive to any beach u wana go too.

Reviewed on Sep. 2, 2025

Where to stay in On Top of The World

Find the best On Top of The World areas and neighborhoods for the activities you enjoy most. Learn more about On Top of The World
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Downtown St. Petersburg

1 out of top 10 points of interest in this area

Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.

Find hotels in Downtown St. Petersburg

On Top of The World Hotel Deals

Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

4 out of 5
333 1st St S, St. Petersburg, FL
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Sep 14 to Sep 15
CA $148
CA $167 total
Sep 14 - Sep 15
includes taxes & fees
Hilton St. Petersburg Bayfront
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $234 per night from Sep 14 to Sep 15
CA $234
CA $319 total
Sep 14 - Sep 15
includes taxes & fees
Hilton Clearwater Beach Resort & Spa
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Sep 14 to Sep 15
CA $210
CA $239 total
Sep 14 - Sep 15
includes taxes & fees
Hotel Alba, Tapestry Collection by Hilton
See all 15,342 properties in On Top of The World
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an On Top of The World vacation package cost?
Maybe less than you imagined — from just CA $591, 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.

Discover the most popular places to visit in On Top of The World

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(136 reviews)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the beautiful beaches in this family-friendly area, or check out its lively bars.

John's Pass Village & Boardwalk
Clearwater Beach

Clearwater Beach

4.5/5(5 reviews)

Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach
Fort De Soto Park which includes a sandy beach

Fort De Soto Park

4.5/5(28 reviews)

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park

Things to do

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $44
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

CA $48
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

CA $51
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.