On Top of The World Holidays

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Your On Top of The World Holiday

Whatever your travel style, you can experience it all with a tailor-made On Top of The World holiday package. Spend your next break uncovering this neighbourhood's golfing and its other appeals. Wondering what to see and do during your trip to On Top of The World? Nearby attractions such as Ruth Eckerd Hall, Eddie C. Moore Softball Complex and Westfield Countryside Mall are good places to start. Expedia is here to help put your travel plans into action. Book your ideal On Top of The World holiday today.

Our guide on 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

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

Our pick of the best 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 AU$525 per night from 31 May to 1 June
AU$525
31 May - 1 June
includes taxes & fees
9.4/10 Exceptional! (3,237 reviews)
We had a fabulous Mother’s Day weekend at Wyndham Grand Clearwater Beach. It also happened to be Country Weekend, which made the experience even more fun and memorable. The entertainment was a huge plus and created such an amazing atmosphere throughout the weekend. The lobby bar staff and pool staff ...

Reviewed on 12 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 refundableReserve now, pay when you stay
The price is AU$230 per night from 24 May to 25 May
AU$230
24 May - 25 May
includes taxes & fees
8.6/10 Excellent! (1,298 reviews)
elevators not working, pool closed for renovations,noicy hallways ,only one electric charger for cars and always not available.

Reviewed on 11 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 AU$369 per night from 26 May to 27 May
AU$369
26 May - 27 May
includes taxes & fees
8.2/10 Very Good! (2,619 reviews)
Room and property appeared run down. Broken patio door, leaking shower head, broken toilet seat. Bathroom faucet was loose. Room overlooked equipment area so even though it was a “gulf view” it was dirty and noisy and they did a poor job trying to cover the equipment. This was very subpar from what ...

Reviewed on 11 May 2026

Hilton Clearwater Beach Resort & Spa
See all 16,128 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 Holidays
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beach holidays
Beach Holidays
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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.

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

White sand and palm trees in Clearwater beach

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
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
Salvador Dali Museum

Salvador Dali Museum

5/5(1 review)

Browse the surrealistic masterpieces of a world-famous Spanish painter in a remarkable building that perfectly suits the style of the art exhibits.

Salvador Dali Museum

Activities

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

AU$52
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

AU$56
per adult
90% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

AU$63
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.