The Best Hotels in Diamond Isle, St. Petersburg - Clearwater - 2026 Updated Prices

Sunset at Clearwater beach with Pier 60 fishing pier, white sand beach dramatic colorful sky

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Where to stay in Diamond Isle

Find the best Diamond Isle 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 Diamond Isle Hotel Reviews

Wyndham Grand Clearwater Beach

10/10 Excellent

"We were only there one night but would go back for a longer stay. Very nice hotel with a beautiful pool and quick access to the beach."

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

When is the best time to go to Diamond Isle?

The best time to visit Diamond Isle is during the spring months of March, April, and May, or in the autumn, from late September through November.

These periods offer the most pleasant weather, with comfortable temperatures and lower humidity, making it ideal for enjoying the island's outdoor activities and beaches. You'll find the island less crowded than during the peak summer season, which means a more relaxed experience and often better value on accommodation and activities.

For those looking to enjoy the island's natural beauty without the bustling crowds, late autumn is particularly good. The sea remains warm enough for swimming into November, and the clear skies are superb for sunsets over the Gulf of Mexico. This is especially good for couples seeking a tranquil getaway.

If you're planning a family holiday, spring break can be popular, but late May offers a good balance of warm weather and fewer crowds before the full summer rush begins.

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 Diamond Isle.

How can I save on a Diamond Isle hotel booking with Expedia?

Members always get our best prices. Find our best Diamond Isle 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 Diamond Isle hotel?

Hotel prices in Diamond Isle 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 Diamond Isle hotels

Hampton Inn & Suites Tampa Airport Avion Park Westshore

Barefoot Beach Club

Crystal Bay Historic Hotel

Hollander Boutique Hotel

Bilmar Beach Resort

Hampton Inn Tampa-International Airport/Westshore

Avalon Hotel Downtown St. Petersburg

Malibu Resort Motel

Belleair Beach Resort Motel

Innisbrook Resort

RumFish Beach at TradeWinds

Tru By Hilton St. Petersburg Downtown Central Ave, FL

Fairfield Inn & Suites by Marriott Clearwater

Home2 Suites by Hilton Largo

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

Hampton Inn Tampa/Rocky Point-Airport

Comfort Suites Tampa Airport North

Cambria Hotel St Petersburg-Madeira Beach Marina

Mari Jean Hotel - All Adults Welcome

Days Inn by Wyndham Clearwater/Gulf to Bay

Where to stay in Diamond Isle

Pass-a-Grille

Downtown St. Petersburg

Sand Key

Sunset Beach

Sunshine Beach

Top Diamond Isle Hotel Reviews

Wyndham Grand Clearwater Beach

Frequently asked questions

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