On Top of The World Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Jul 21 - Jul 28

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    7 nights
    3.0 star property
    9.2/10 - Wonderful (526 reviews)
    "Excellent service!!"
    Reviewed June 6, 2026
    Roundtrip • Montreal (YUL) - Tampa (TPA)
    YUL - TPA • 1 stop TPA - YUL • 1 stop
    CA $2,866
    CA $1,766
    per traveller
    found 1 day ago
    Cedar Cove Resort and Cottages
  • Presidential Quadruple Room, Bay View | Living area
    Jul 30 - Aug 6

    CW Hotel + Flight

    Clearwater Beach
    7 nights
    2.0 star property
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $3,170
    CA $1,848
    per traveller
    found 8 hours ago
    CW Hotel
  • 2 bedrooms, memory foam beds, in-room safe, blackout drapes
    Jul 20 - Jul 27

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    7 nights
    4.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    "We stayed for one weekend and the experience was disappointing. The pool was closed for maintenance the entire time and no one on staff seemed concerned. The microwave in our room did not work, which made simple things inconvenient. The hotel is not actually right off the beach and you end up walking what feels like two miles of sand just to reach the water. You also cannot see the ocean from the rooms. All those large windows only give you views of sand, trees, and the street. For a place that..."
    Reviewed June 7, 2026
    Roundtrip • Montreal (YUL) - Tampa (TPA)
    YUL - TPA • 1 stop TPA - YUL • 1 stop
    CA $2,953
    CA $1,940
    per traveller
    found 1 day ago
    Ocean Club Treasure Island Hotel
  • Exterior
    Jul 21 - Jul 28

    The Don CeSar + Flight

    St. Pete Beach
    7 nights
    4.0 star property
    9.2/10 - Wonderful (1,163 reviews)
    "Amazing hotel, timeless and beautiful."
    Reviewed June 6, 2026
    Roundtrip • Montreal (YUL) - Tampa (TPA)
    YUL - TPA • 1 stop TPA - YUL • 1 stop
    CA $2,981
    CA $1,961
    per traveller
    found 1 day ago
    The Don CeSar
  • Exterior
    Jul 30 - Aug 6

    The Marker + Flight

    Clearwater Beach
    7 nights
    2.0 star property
    6.0/10 - (3 reviews)
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $3,443
    CA $2,387
    per traveller
    found 8 hours ago
    The Marker

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
Pass-a-Grille

Pass-a-Grille

1 out of top 10 points of interest in this area

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotels in Pass-a-Grille

On Top of The World Hotel Deals

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $418 per night from Jun 11 to Jun 12
CA $418
CA $528 total
Jun 11 - Jun 12
includes taxes & fees
9.4/10 Exceptional! (3,327 reviews)
"Wonderful stay! Would go back"

Reviewed on Jun 7, 2026

Wyndham Grand Clearwater Beach
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $256 per night from Jun 18 to Jun 19
CA $256
CA $291 total
Jun 18 - Jun 19
includes taxes & fees
8.6/10 Excellent! (1,352 reviews)
"Excellent service, clean property, great location and awesome amenities."

Reviewed on Jun 7, 2026

The Westin Tampa Bay
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 $313 per night from Jun 29 to Jun 30
CA $313
CA $409 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (2,677 reviews)
"Rooms are extremely small and the partial view was a joke we could not open the door because the AC fans for the facility was blowing straight for our door causing a loud sound all night. But Beach view was perfect (NOT FROM OUR ROOM) But private beach was nice."

Reviewed on Jun 7, 2026

Hilton Clearwater Beach Resort & Spa
See all 16,193 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 , 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

Aerial view of the pink-tinged waters reflecting the vibrant sunset hues next to the John's Pass Village & Boardwalk, Treasure Island, Florida, United States.

John's Pass Village & Boardwalk

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

John's Pass Village & Boardwalk
Aerial sunset view of Clearwater beach and Sand key in Western Florida on the Mexican Gulf coast with vacation homes, hotels and bridges connecting

Clearwater Beach

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

Fort De Soto Park

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

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $51
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $51
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

CA $61
per adult
100% of travellers recommend
Pirate Adventure Cruise - John's Pass
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.