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

RumFish Beach at TradeWinds

8/10 Good

"First time staying at Rumfish and we were automatically upgraded to a Gulf view! No balcony, but floor to ceiling sliding glass door with a railing which worked perfectly. The pool was directly below us and the view was amazing. Room was a little dated, but we had all the essentials, stove, microwave refrigerator. Too bad no one seemed to know where the Publix and Walmart was. We were told we would have to go to Tampa, but they are located a few miles south of the resort and can use the free shuttle to get there. Great Restaurants are within walking distance and TradeWinds has made some nice upgrades, adding more eateries. We stayed there several years ago. Location is excellent! Staff is friendly and cannot say enough about our checkin/out service. Hubby lost his CC the night before checking out. I made mention to the agent and he asked if I wanted him to leave information with security. I handed him the information, he went behind the counter and came back with our CC in hand! What a relief and must say quite surprised and very grateful. Thank you staff at RumFish Resort. We will be back 👍"

Courtyard by Marriott Clearwater Beach

4/10 Poor

"Force you into destination fees that they only tell you about once you check in and you’re paying for amenities that suck. The room felt like staying in a low budget motel and the shower was dirty and water everywhere because their design is horrible. Avoiding this company moving forward."

Tropical Palms Hotel

6/10 Okay

"The front desk was very unprofessional and on their cellphones while checking in. The room was clean but the rest of the hotel was not so clean. Also, no working ice machines, they were both broken. Besides that it’s a quiet place to stay very close to the airports and about 35 min away from Clearwater beach. Also, plenty of restaurants in the area to eat."

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

RumFish Beach at TradeWinds

Hampton Inn Tampa-International Airport/Westshore

Bilmar Beach Resort

Hollander Boutique Hotel

Barefoot Beach Club

Crystal Bay Historic Hotel

Fairfield Inn & Suites by Marriott Clearwater

Tru By Hilton St. Petersburg Downtown Central Ave, FL

Belleair Beach Resort Motel

Hyatt House Tampa Airport Westshore

Island Grand at TradeWinds

Hampton Inn & Suites Tarpon Springs

Innisbrook Resort

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

Home2 Suites by Hilton Largo

GALAXY HOTEL

Pier House 60 Clearwater Beach Marina Hotel

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Comfort Inn & Suites Northeast - Gateway

Where to stay in Diamond Isle

Pass-a-Grille

Downtown St. Petersburg

Sand Key

Sunset Beach

Sunshine Beach

Top Diamond Isle Hotel Reviews

RumFish Beach at TradeWinds

Frequently asked questions

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