On Top of The World Vacation Packages

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Top Holiday Package Deals in On Top of The World

Price found within the past 48 hours. Click for updated prices.
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
7.6/10 Good! (1,005 reviews)
Completely remodeled- looks great!

Reviewed on Jun. 1, 2024

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Jul. 26 - Jul. 31
found 13 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
9.6/10 Exceptional! (302 reviews)
Cleanliness of the beaches and not as packed

Reviewed on Jun. 5, 2024

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Wesley Chapel South
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
6.8/10 (1,004 reviews)
Beautiful grounds. Rooms were clean and spacious. Would stay here again

Reviewed on May 29, 2024

Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9/10 Wonderful! (1,244 reviews)
Was very clean and relaxing

Reviewed on Jun. 4, 2024

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jul. 21 - Jul. 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
8.8/10 Excellent! (1,000 reviews)
Lively motel with great location and access to the beach. Friendly staff. Kitchenette is great convenience. Would stay again.

Reviewed on Jun. 2, 2024

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

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotel + flight trips in Pass-a-Grille

On Top of The World Hotel Deals

RumFish Beach Resort by TradeWinds
RumFish Beach Resort by TradeWinds
4 out of 5
6000 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Jun. 6 to Jun. 7
CA $233
CA $348 total
includes taxes & fees
Jun 6 - Jun 7
8.2/10 Very Good! (1,021 reviews)
"."

Reviewed on Jun. 4, 2024

RumFish Beach Resort by TradeWinds
Sirata Beach Resort
Sirata Beach Resort
3 out of 5
5300 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Jun. 27 to Jun. 28
CA $213
CA $302 total
includes taxes & fees
Jun 27 - Jun 28
7.2/10 Good! (2,264 reviews)
"Good atmosphere"

Reviewed on Jun. 4, 2024

Sirata Beach Resort
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4 out of 5
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Jul. 5 to Jul. 6
CA $190
CA $216 total
includes taxes & fees
Jul 5 - Jul 6
8.6/10 Excellent! (1,028 reviews)
"I liked the location. I would like to have had a microwave in the room."

Reviewed on Jun. 4, 2024

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
See all 16,063 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an On Top of The World vacation package cost?
Maybe less than you imagined — from just CA $557, actually! By combining hotels, flights and car rentals into a customized vacation 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 vacation 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 travelers 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 vacation?
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 vacation!
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 organizing 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 vacation 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 vacation 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

Image for John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(136 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 check out its top-notch restaurants.

John's Pass Village & Boardwalk
Image for Tropicana Field

Tropicana Field

4/5(26 reviews)

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the top-notch restaurants while you're in the area.

Tropicana Field
Image for Fort De Soto Park

Fort De Soto Park

4.5/5(28 reviews)

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park

Things to do

Image for StarLite Majesty Evening Yacht Cruise Clearwater

StarLite Majesty Evening Yacht Cruise Clearwater

CA $43
Per adult
86% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Image for 2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

CA $47
Per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
Image for Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

CA $81
Per adult
100% of travellers recommend
Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar
See all activities in St. Petersburg - Clearwater

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.