On Top of The World Holidays from £862

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Your On Top of The World Holiday

Let our On Top of The World holiday packages take you to a destination where unforgettable memories are waiting to be made. While it's especially noted for its golfing, there's plenty more to like about this neighbourhood. Your trip to On Top of The World wouldn't be complete without stopping by top attractions nearby such as Ruth Eckerd Hall, Eddie C. Moore Softball Complex and Westfield Countryside Mall. Don't just imagine it — do it! Lock in your ideal On Top of The World holiday with Expedia and travel your way.

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was £1,153, price is now £862 per person
£862
per person
9 Sept - 16 Sept
found 1 day ago
Return flight included
London (LHR) to Tampa (TPA)
8/10 Very good! (127 reviews)
We spent great time celebrating the 4th of July with live music and pool entertainment. This place is very relax far from metropolitan area.

Reviewed on 10 Jul 2026

Landing Apartments near Sun City Center and Riverview

Landing Apartments near Sun City Center and Riverview

4 out of 5
Price was £1,765, price is now £1,391 per person
£1,391
per person
13 Aug - 20 Aug
found 1 day ago
Return flight included
London (LHR) to Tampa (TPA)
8.8/10 Excellent! (30 reviews)
Very clean and quite, near to the main beaches, have everything that you need, 100 recomended

Reviewed on 24 Jun 2026

Hyatt Place Tampa Downtown

Hyatt Place Tampa Downtown

3 out of 5
Downtown Tampa
Price was £1,322, price is now £1,048 per person
£1,048
per person
9 Sept - 16 Sept
found 1 day ago
Return flight included
London (LHR) to Tampa (TPA)
9.4/10 Exceptional! (2,084 reviews)
Clean room. For just a short stay the desk personnel was very polite and the bar attendees very helpful.

Reviewed on 10 Jul 2026

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Beach Park
Price was £1,241, price is now £990 per person
£990
per person
9 Sept - 16 Sept
found 1 day ago
Return flight included
London (LHR) to Tampa (TPA)
8.6/10 Excellent! (1,833 reviews)
Very clean, spacious and wonderfully located hotel.

Reviewed on 9 Jul 2026

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Price was £1,229, price is now £988 per person
£988
per person
9 Sept - 16 Sept
found 1 day ago
Return flight included
London (LHR) to Tampa (TPA)
8.6/10 Excellent! (2,669 reviews)
Friendly staff, clean rooms, and the comforter was very comfortable!

Reviewed on 10 Jul 2026

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

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 £242 per night from 2 Aug to 3 Aug
£242
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (3,516 reviews)
"."

Reviewed on 10 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
Fully refundableReserve now, pay when you stay
The price is £192 per night from 9 Aug to 10 Aug
£192
9 Aug - 10 Aug
includes taxes & fees
8.2/10 Very good! (2,808 reviews)
"We loved our stay! Will be going back next time we go to Florida!"

Reviewed on 10 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 £182 per night from 9 Aug to 10 Aug
£182
9 Aug - 10 Aug
includes taxes & fees
8.2/10 Very good! (2,133 reviews)
"Beautiful property. Well maintained. The only amenity we would have loved is an ice machine. Otherwise, pools were clean. Lots of eating options. Ample parking. Excellent location."

Reviewed on 10 Jul 2026

RumFish Beach at TradeWinds
See all 16,290 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an On Top of The World travel package cost?
Handcraft your On Top of The World travel package from a low £862. Pick from any combination of flights, hotels and rental cars to build the escape you've been dreaming about. Be sure to add on a few activities!
If I'm not able to travel, can I cancel my On Top of The World travel package?
Yes you can, and we're here to help. You may be able to cancel or change your On Top of The World travel package for free within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your travel plans unexpectedly change, browse our Customer Service Portal for further information.
How do I get a cheap travel package to On Top of The World?
Our On Top of The World travel packages mean plenty of savings for the savvy explorer. For the best deals, simply combine your hotel, flights and extras (such as activities) into an affordable package. But cheap prices are just the beginning of your next unforgettable adventure. Book with Expedia and and you'll have over 550 air carriers and 1,000,000 hotels worldwide to choose from. No matter your style or budget, there's a travel package here just for you.
Does Expedia offer Book Now, Pay Later On Top of The World holidays?
Expedia has joined forces with online lender Klarna to make booking your next break easier on your hip pocket. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to pick from, so you're sure to find one that fits into your budget. Consider these flexible payment options:

  • Pay monthly holidays: Klarna has easy monthly payment plans that suit all types of budgets, so you can lock in that well-deserved holiday sooner.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you see an awesome deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you secure your getaway.

Where should I stay in On Top of The World?
A trip to On Top of The World isn't complete without seeing Bright House Field, Ruth Eckerd Hall and Eddie C. Moore Softball Complex. Stay close to these top sights and make sightseeing simple.
What are the top hotels in On Top of The World?
SureStay Hotel by Best Western St. Pete Clearwater Airport and Residence Inn by Marriott Clearwater Downtown are two of the most sought-after hotels in On Top of The World. Why not check out the amenities and rates at each and then make a decision?
How far in advance should I book my On Top of The World holiday?
Reserving your seat early with Expedia means one less thing to have to worry about. A number of air carriers advertise prices up to 12 months prior to departure dates. This is generally the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to On Top of The World sometimes occur a few weeks before departure.
What does an Expedia On Top of The World travel package include?
Flights, hotels and a cool set of wheels for all your fun road trip adventures. Simply pick and choose your preferred bundle and get access to incredible deals. Once you've made your booking, add on some sightseeing tours and watch your savings stack up. When it comes to organising your On Top of The World holiday, you're in charge!
What should I know before booking an On Top of The World travel package?
Whether it's relaxation or adventure you're seeking, an On Top of The World travel package lets you plan your escape your way. Plus, you'll score great discounts just for combining your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with an On Top of The World Expedia travel package?
Definitely. Expedia has over 550 airline partners to pick from around the world. With such a big range of choice, finding the ideal carrier to get you to On Top of The World will be a breeze.

Things to do

Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

£28
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

£28
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
Clearwater Beach: Dolphin & Island Sandbar Cruise

Clearwater Beach: Dolphin & Island Sandbar Cruise

£21
per adult
90% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
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. Flight-inclusive packages are ATOL protected.