On Top of The World Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp16.000.000 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 Rp4.628.506 per night from 8 Jul to 9 Jul
Rp4.628.506
Rp5.934.429 total
8 Jul - 9 Jul
includes taxes & fees
9.4/10 Exceptional! (3,400 reviews)
"This truly was one of the best beach hotel experiences I’ve ever had. Right off the bat the front desk guy got us additional water bottles when we checked in and additionally gave us an hour later check out. Each floor has an ice machine and filtered water station- never seen this at a hotel so this ..."

Reviewed on 22 Jun 2026

Wyndham Grand Clearwater Beach
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 Rp3.497.774 per night from 6 Jul to 7 Jul
Rp3.497.774
Rp4.656.636 total
6 Jul - 7 Jul
includes taxes & fees
Hilton Clearwater Beach Resort & Spa
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is Rp2.868.224 per night from 28 Jun to 29 Jun
Rp2.868.224
Rp4.347.612 total
28 Jun - 29 Jun
includes taxes & fees
8.2/10 Very Good! (2,053 reviews)
"This trip was supposed to be something special for my family. For starters there was a huge wasp nest on our balcony, which we were told would be taken care of - never was. Then our AC stopped working - they did offer to move us but by then it was day 3 of our trip. I was told that they were going ..."

Reviewed on 22 Jun 2026

RumFish Beach at TradeWinds
See all 16,244 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

Salvador Dali Museum

Salvador Dali Museum

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
Sand Key Park

Sand Key Park

If a restful holiday is part of your travel plans, Sand Key Park might be the perfect place to visit during your trip to Clearwater Beach. Stroll along the seaside in this family-friendly area or visit its top-notch restaurants.

Sand Key Park
Eckerd College

Eckerd College

Walk around the campus at Eckerd College as part of your travels around St. Petersburg. Amble around this family-friendly area's beautiful beaches and enjoy its lively bars.

Eckerd College

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

Rp659.190
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

Rp651.081
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

Rp797.415
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.