On Top of The World Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

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
5/5(3 area reviews)

As you view this neighborhood’s iconic pink hotel it feels as if you’ve crossed into the past. Find beautiful beaches and serene enjoyment here.

Find hotels in Pass-a-Grille

Top hotels in On Top of The World

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 €303 per night from 31 May to 1 Jun
€303
31 May - 1 Jun
includes taxes & fees
9.4/10 Exceptional! (3,255 reviews)
"Wonderful all around. Just one tiny detail from the check in desk, where we could sense the attendant was probably dealing with some personal matters and projected that to her work."

Reviewed on 18 May 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 refundable
The price is €169 per night from 7 Jun to 8 Jun
€169
7 Jun - 8 Jun
includes taxes & fees
8.6/10 Excellent! (1,310 reviews)
"Sadly the pool was not open however Jimmy & Jenny at the bar were supre friendly and gave great service. The hotel staff was friendly"

Reviewed on 18 May 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 €233 per night from 25 May to 26 May
€233
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,626 reviews)
"The amenities I read online were not free and even after showing the hotel they did nothing about it."

Reviewed on 18 May 2026

Hilton Clearwater Beach Resort & Spa
See all 16,103 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.

Frequently asked questions

How much does an On Top of The World holiday package cost?
Maybe less than you imagined — from just , actually! By combining hotels, flights and car rentals into a customized holiday 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 holiday 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 travellers 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 holiday?
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 holiday!
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 organising 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 holiday 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 holiday 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.

Popular places to visit

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

4.5/5(34 reviews)

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 visit its lively bars.

John's Pass Village & Boardwalk
Fort De Soto Park

Fort De Soto Park

4.5/5(25 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
Vinoy Park

Vinoy Park

While area beaches are abundant, it’s convenient to have this lovely spot right in the city. Lounge under a palm tree and enjoy the frequent entertainment.

Vinoy Park

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

€32
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

€38
per adult
100% of travellers recommend
Pirate Adventure Cruise - John's Pass
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

€34
per adult
90% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
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.