The Best Hotels in On Top of The World, St. Petersburg - Clearwater - 2026 Updated Prices

Top the best beaches in the world. Wide and long Ocean beach. Summer or autumn vacation. Location Clearwater beach Florida. American Coast or shore. Island in Gulf of Mexico. Aerial view of city.

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Where to stay in On Top of The World

Find the best On Top of The World areas for the activities you enjoy most.

Pass-a-Grille

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.

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Downtown St. Petersburg

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

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Sand Key

If you're spending some time in Sand Key, Belleair Beach and Sand Key Park are top sights worth seeing.

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Sunset Beach

Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like Sunset Beach and St. Petersburg Municipal Beach at Treasure Island.

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Sunshine Beach

While visiting Sunshine Beach, you might make a stop by sights like St. Petersburg Municipal Beach at Treasure Island and St. Petersburg - Clearwater Beaches.

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Top On Top of The World Hotel Reviews

Hilton Tampa Airport Westshore

8/10 Good

"Very nice and affordable worth the money"

Bilmar Beach Resort

4/10 Poor

"Our first room, my issue was the carpet. It was extremely nasty. My feet stuck to it as I walked from the front door to the patio. I went down to exchange my room. I had to complain quite a lot to get them to switch me rooms with no carpet once I did that the room that I went into the bed, you could tell as soon as you seen it half of it, the frame was broke as far as cleaning, I don’t think the floors have been mopped since the building has been built totally overpaid for this experience"

Hyatt Regency Clearwater Beach Resort and Suites

2/10 Terrible

"#1Well phone in room worked half the time #2 Went down stairs to get my truck which we were paying 40 a day and walked up to young man at valet handed him my ticket and he didn't even take it at first he looked at me and said what's this arrogantly as I was suppose to know the pro ess of call down be4 you come get your car or truck very unfriendly & arroganty sarcastic. #3Went to breakfast at the property called shore and the wait was super long not knowing it was a buffet or a la cart we went thinking it was a la cart only so we actualy went to be seated and pay top dollar when the finaly got to us it was like 30to45 minutes later waiter was un focused u engaged clearly was somewhere else no napkins were brought no starts either and I asked for a bowl.of fruit to eat with my breakfast well they forgot and didn't bring that I mentioned to 1 waitress she said she would get that for me never came out my breakfast was already at the table mind you #4Well my wifes steak as well came uncooked super bloody she asked for to medium well so they took .y wife's plate and brought her another 20.minutes later when I already had finished earing meanwhile my fruit never brought out so that's service at the SHORE in the hotel #5 Ive been world Hyatt member for over 7 years related this to the man at the front desk he confirmed my status to attach the stay for credit to.my points as well as that did not get recorded or do e as he said he was doing at checkin. #6 Another disappointment no in"

RumFish Beach at TradeWinds

4/10 Poor

"I stayed at the TradeWinds years ago and had such a wonderful experience but it was not at the Rum Fish Resort. Unfortunately, this stay was nothing like what I experienced in the past. We specifically booked a room with two queen beds, but upon arrival were told none were available and were given two double beds instead. My husband is 6’2”, so this made for a very uncomfortable stay right from the start. The room had a very strong mildew smell that was impossible to ignore. It honestly made the room feel unclean and unpleasant. We had also requested a quiet room location, hoping for a relaxing beach weekend. Instead, we were placed directly above and overlooking a massive beach party/event with 1,500 people. The event started around 6 PM and was followed by extensive breakdown and cleanup noise afterward until late in the evening. To make matters worse, we paid extra for front-row beach chairs, only to be seated in front of what felt like a nonstop frat party on the beach. Hundreds of college-aged kids were packed into the area drinking and partying loudly from late morning until evening. None of these kids were from our hotel, they kept pouring in from a walkway between hotels. Overall, we were extremely disappointed in our stay. We live locally and have seen the beautiful commercials for TradeWinds for years, but the reality was nothing like what is advertised."

Frequently asked questions

What other neighbourhoods are similar to On Top Of The World?

While On Top Of The World is a unique 55+ community, areas like Sun City Center and The Villages offer similar lifestyles for those seeking an active adult community in Florida.

Sun City Center, located south of Tampa, is a well-established 55+ community known for its extensive amenities and a wide range of social clubs and activities. It features multiple golf courses, community centres with swimming pools, fitness facilities, and various craft rooms. It's designed for residents who enjoy a full social calendar and easy access to healthcare facilities.

The Villages, situated in central Florida, is one of the largest active adult communities in the world. It's characterised by its distinct town squares, each offering live entertainment nightly, a multitude of shops, and restaurants. The community boasts numerous golf courses, recreation centres with high-end fitness equipment, and a vast network of golf cart-friendly paths.

When is the best time to go to On Top Of The World?

The best time to go to On Top Of The World is from late autumn through to late spring, specifically November to May, when the weather is most pleasant.

During these months, you'll experience comfortable temperatures, typically ranging from the low 20s to high 20s Celsius (70s to 80s Fahrenheit), and lower humidity. This makes it ideal for enjoying outdoor activities, whether it's a round of golf, a swim in a heated pool, or simply relaxing on your lanai. It's great for those looking to escape colder climates and enjoy the Florida sunshine without the intense heat and humidity of summer.

For those who enjoy a lively social calendar, winter (December to February) is particularly popular. This is when the community often has a full schedule of events, clubs, and activities, offering plenty of opportunities to socialise and meet new people. It's a great time for solo travellers or couples who appreciate a busy, engaging environment with a strong sense of community.

While the summer months (June to October) offer lower prices, they come with higher temperatures, significant humidity, and a greater chance of afternoon thunderstorms or tropical weather.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in On Top of The World.

How can I save on a On Top of The World hotel booking with Expedia?

Members always get our best prices. Find our best On Top of The World hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.

How much is the nightly rate at a On Top of The World hotel?

Hotel prices in On Top of The World often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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Our top choices for On Top of The World hotels

Quality Inn Tampa Airport - Cruise Port

Hotel South Tampa & Suites

Hampton Inn & Suites Tampa Airport Avion Park Westshore

Bilmar Beach Resort

RumFish Beach at TradeWinds

Hampton Inn Tampa-International Airport/Westshore

Hollander Boutique Hotel

Barefoot Beach Club

Tropical Palms Hotel

Crystal Bay Historic Hotel

Mint House Tampa Downtown by Kasa

Fairfield Inn & Suites by Marriott Clearwater

Country Inn & Suites by Radisson, Tampa Airport North, FL

Malibu Resort Motel

Island Grand at TradeWinds

Innisbrook Resort

Tru By Hilton St. Petersburg Downtown Central Ave, FL

Hampton Inn Tampa/Rocky Point-Airport

Home2 Suites by Hilton Largo

Hyatt House Tampa Airport Westshore

Where to stay in On Top of The World

Pass-a-Grille

Downtown St. Petersburg

Sand Key

Sunset Beach

Sunshine Beach

Top On Top of The World Hotel Reviews

Hilton Tampa Airport Westshore

Frequently asked questions

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