On Top of The World Holidays

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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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Pass-a-Grille

Pass-a-Grille is popular for its beaches, and if you're looking for more to see and do, you might think about a trip to Pass-a-Grille Beach or St. Petersburg - Clearwater Beaches.

Find hotels in Pass-a-Grille

Top hotels in On Top of The World

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 4.454.000 ₫ per night from 12 Aug to 13 Aug
4.454.000 ₫
6.069.230 ₫ total
12 Aug - 13 Aug
includes taxes & fees
8/10 Very Good! (2,062 reviews)
"Everything walking distance"

Reviewed on 25 Jul 2025

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 3.310.631 ₫ per night from 4 Aug to 5 Aug
3.310.631 ₫
3.757.565 ₫ total
4 Aug - 5 Aug
includes taxes & fees
8.6/10 Excellent! (2,026 reviews)
"Excellent, for the Price"

Reviewed on 27 Jul 2025

Hotel Alba, Tapestry Collection by Hilton
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 7.504.794 ₫ per night from 17 Aug to 18 Aug
7.504.794 ₫
9.514.255 ₫ total
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (2,438 reviews)
"We loved the proximity to the beach and the beach chairs /umbrellas. Pool was a bit crowded , but to be expected since there is only one pool. Elevators are very slow and at times only one was working. We are still waiting on our itemized invoices as the system was new and they were not able to provide ..."

Reviewed on 26 Jul 2025

Wyndham Grand Clearwater Beach
See all 15,205 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 1null000null000 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

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4/5(33 reviews)

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

John's Pass Village & Boardwalk
Fort De Soto Park featuring a beach

Fort De Soto Park

4.5/5(25 reviews)

Enjoy the beautiful sunsets and explore Fort De Soto Park, a lovely green space in Tierra Verde. Discover the top-notch restaurants and great live music in this family-friendly area.

Fort De Soto Park
Salvador Dali Museum featuring night scenes and modern architecture

Salvador Dali Museum

5/5(20 reviews)

You can spend time browsing the exhibits at Salvador Dali Museum during your trip to St. Petersburg. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Salvador Dali Museum