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
A beach with people, a city skyline, and a distinctive pink building.

Pass-a-Grille

1 out of top 10 points of interest in this area
5/5(3 area reviews)

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 St. Petersburg - Clearwater Beaches or Gulf Beaches Historical Museum.

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 5.872.134 ₫ per night from 21 Jul to 22 Jul
5.872.134 ₫
7.675.281 ₫ total
21 Jul - 22 Jul
includes taxes & fees
9.4/10 Exceptional! (3,460 reviews)
"Excellent beach view wth nice ambiance"

Reviewed on 3 Jul 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
The price is 5.382.615 ₫ per night from 14 Jul to 15 Jul
5.382.615 ₫
7.121.962 ₫ total
14 Jul - 15 Jul
includes taxes & fees
8.2/10 Very good! (2,749 reviews)
"My husband and I booked to stay here for our wedding anniversary. It is close to our daughter so we chose this hotel. We were very disappointed!! Upon arriving, we realize you can only valet your car for guests. They charge $40/day to park your car there. So you also need to tip the valet. Atleast ..."

Reviewed on 3 Jul 2026

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 4.708.539 ₫ per night from 9 Jul to 10 Jul
4.708.539 ₫
6.954.573 ₫ total
9 Jul - 10 Jul
includes taxes & fees
8.2/10 Very good! (2,099 reviews)
"Beach staff was great, pool staff and games were fun!"

Reviewed on 3 Jul 2026

RumFish Beach at TradeWinds
See all 16,234 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.