On Top of The World Holidays from AU$521

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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.

Top Holiday Package Deals in On Top of The World

Price found within the past 48 hours. Click for updated prices.
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
North Trail
Price was AU$606, price is now AU$521 per person
AU$521
per person
25 Nov - 28 Nov
found 4 hours ago
Return flight included
New York (NYC) to Tampa (TPA)
8.4/10 Very Good! (2,128 reviews)
Good value for the price

Reviewed on 24 Oct 2025

Carlisle Inn

Carlisle Inn

3.5 out of 5
Pinecraft
Price was AU$849, price is now AU$672 per person
AU$672
per person
25 Nov - 28 Nov
found 4 hours ago
Return flight included
New York (NYC) to Tampa (TPA)
10/10 Exceptional! (2,057 reviews)
The room was very clean, the staff were very friendly and easy to talk to! Very nice hotel! The only thing was, I was expecting different kind of breakfast. It’s an Amish hotel, so I was expecting some home cooked food. Also, a little more option, especially offering bacon!

Reviewed on 23 Oct 2025

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
Price was AU$768, price is now AU$644 per person
AU$644
per person
25 Nov - 28 Nov
found 4 hours ago
Return flight included
New York (NYC) to Tampa (TPA)
8.2/10 Very Good! (1,469 reviews)
Wonderful views. Stayed in October. Work still be completed on bottom floor rooms. Lots of construction workers. Very few people in the resort area. Felt like we were the only ones there at times. The only complaint we had on the rooms was the floors did not get mopped often. Nightly music and campfire s'mores. We walked everywhere or got a beach ride. Very peaceful. We will be back!

Reviewed on 22 Oct 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Price was AU$1,016, price is now AU$860 per person
AU$860
per person
25 Nov - 28 Nov
found 4 hours ago
Return flight included
New York (NYC) to Tampa (TPA)
9.4/10 Exceptional! (2,723 reviews)
Resort was perfect and staff was very friendly

Reviewed on 24 Oct 2025

Pier House 60 Clearwater Beach Marina Hotel

Pier House 60 Clearwater Beach Marina Hotel

3 out of 5
Price was AU$691, price is now AU$589 per person
AU$589
per person
25 Nov - 28 Nov
found 4 hours ago
Return flight included
New York (NYC) to Tampa (TPA)
8.8/10 Excellent! (1,785 reviews)
2nd time staying here. Brought family and friends up for our wedding. We all stayed here. Hotel is clean. Love the rooftop bar. Shopping/dining/beach short walking distance. Only complaint is lack of shower pressure.

Reviewed on 23 Oct 2025

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
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Downtown St. Petersburg

1 out of top 10 points of interest in this area

Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.

Find hotels in Downtown St. Petersburg

Our pick of the best On Top of The World Hotel Deals

DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
3050 N Rocky Point Dr W, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is AU$134 per night from 23 Nov to 24 Nov
AU$134
23 Nov - 24 Nov
includes taxes & fees
8/10 Very Good! (1,025 reviews)
We didn’t eat breakfast. We had dinner and the chicken was cold and not cooked throughly. The chicken was sent back two times and it was returned in the same way.

Reviewed on 18 Oct 2025

DoubleTree by Hilton Tampa Rocky Point Waterfront
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 AU$244 per night from 23 Nov to 24 Nov
AU$244
23 Nov - 24 Nov
includes taxes & fees
8.6/10 Excellent! (2,288 reviews)
Very clean and pleasant staff

Reviewed on 18 Oct 2025

Hotel Alba, Tapestry Collection by Hilton
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$372 per night from 30 Oct to 31 Oct
AU$372
30 Oct - 31 Oct
includes taxes & fees
8/10 Very Good! (2,268 reviews)
Great location and amenities.

Reviewed on 19 Oct 2025

Hilton Clearwater Beach Resort & Spa
See all 15,364 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.
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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 AU$521, 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

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
Salvador Dali Museum featuring night scenes and modern architecture

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
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

Activities

The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

AU$57
per adult
88% 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$53
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
Stunning view of dolphins in St. Petersburg, Florida

Dolphin Racer Speedboat Adventure

AU$43
per adult
92% of travellers recommend
Dolphin Racer Speedboat Adventure
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.