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?

Many Expedia hotel reservations are refundable, provided that you cancel before the hotel’s cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Diamond Isle hotel for you.

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.

10 Best Hotels in Diamond Isle, St. Petersburg - Clearwater for 2026

A beach with a pier, beach umbrellas, and a lifeguard tower.

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Our top choices for Diamond Isle hotels

1. Fairfield Inn & Suites by Marriott Clearwater Beach

0.5 km from Diamond Isle

Billy

CA $191 total

includes taxes & fees

Sep 9 - Sep 10

2. Pier House 60 Clearwater Beach Marina Hotel

1.6 km from Diamond Isle

John

CA $248 total

includes taxes & fees

Sep 9 - Sep 10

3. Comfort Suites Clearwater - Dunedin

2.6 km from Diamond Isle

Ronald

CA $162 total

includes taxes & fees

Sep 24 - Sep 25

Suite, 2 Bedrooms, Ocean View, Oceanfront (Full Kitchen) | Terrace/patio

4. Hyatt Regency Clearwater Beach Resort and Suites

1.8 km from Diamond Isle

Cathy

CA $370 total

includes taxes & fees

Sep 3 - Sep 4

5. ChartHouse Clearwater Beach Marina Hotel

1.6 km from Diamond Isle

SHANNON

CA $255 total

includes taxes & fees

Sep 7 - Sep 8

6. Residence Inn by Marriott Clearwater Downtown

3.9 km from Diamond Isle

Aimee

CA $211 total

includes taxes & fees

Sep 9 - Sep 10

7. Devon Shores

1.9 km from Diamond Isle

Antonio

CA $163 total

includes taxes & fees

Sep 17 - Sep 18

8. SpringHill Suites by Marriott Clearwater Beach

1.8 km from Diamond Isle

Mirtha

CA $237 total

includes taxes & fees

Sep 9 - Sep 10

9. CW Resort

1.1 km from Diamond Isle

Salina

CA $388 total

includes taxes & fees

Sep 23 - Sep 24

Outdoor pool, pool umbrellas, sun loungers

10. Wyndham Grand Clearwater Beach

1.6 km from Diamond Isle

Maria

CA $394 total

includes taxes & fees

Sep 7 - Sep 8

11. Holiday Inn & Suites Clearwater Beach by IHG

2.4 km from Diamond Isle

Cindy

CA $235 total

includes taxes & fees

Sep 7 - Sep 8

12. AC Hotel Clearwater Beach

2 km from Diamond Isle

Daniel

CA $249 total

includes taxes & fees

Sep 9 - Sep 10

13. Edge Hotel Clearwater Beach

2.3 km from Diamond Isle

Sherie

CA $259 total

includes taxes & fees

Sep 30 - Oct 1

14. Clearwater Beach Hotel

2.3 km from Diamond Isle

Mindy

CA $161 total

includes taxes & fees

Sep 8 - Sep 9

15. Holiday Inn Express Hotel & Suites Clearwater North-Dunedin by IHG

4.3 km from Diamond Isle

kameron

CA $210 total

includes taxes & fees

Sep 30 - Oct 1

16. Gulfview Hotel on the Beach

2.4 km from Diamond Isle

Lucia

CA $167 total

includes taxes & fees

Oct 1 - Oct 2

17. Dolphin Sands Clearwater Beach, an Ascend Collection Hotel

2.5 km from Diamond Isle

Ashley

CA $252 total

includes taxes & fees

Sep 29 - Sep 30

18. Hampton Inn & Suites Clearwater Beach

2.4 km from Diamond Isle

Edgardo

CA $300 total

includes taxes & fees

Sep 30 - Oct 1

19. The Grant Street Inn Dunedin Downtown Historic District, an Ascend Collection Hotel

4.3 km from Diamond Isle

Lynn

CA $189 total

includes taxes & fees

Sep 9 - Sep 10

20. La Quinta Inn by Wyndham Clearwater Central

9.2 km from Diamond Isle

Noemi

CA $134 total

includes taxes & fees

Sep 9 - Sep 10

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Where to stay in Diamond Isle

Find the best Diamond Isle areas and neighborhoods for the activities you enjoy most. Learn more about Diamond Isle

A waterfront promenade with palm trees, a canal, and modern high-rise buildings in the background.

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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A sandy beach with dunes and a clear sky.

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.

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A beach with white sand, a red lifeguard tower, and buildings in the background.

Sand Key

While visiting Sand Key, you might make a stop by sights like Belleair Beach and Sand Key Park.

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A wooden boardwalk leading to the ocean, surrounded by greenery.

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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A coastal city with a large beach, a prominent pink building, and a marina.

Don Cesar

Don Cesar might not have many top sights, but Splash Island Water Park and Pass-a-Grille Beach are two attractions nearby that you can check out.

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Top Diamond Isle Hotel Reviews

Hilton Clearwater Beach Resort & Spa

10/10 Excellent

"Awesome location"

The Beachcomber

10/10 Excellent

"We had a wonderful stay! The location was perfect, right by the beach with beautiful views and easy access to everything. The room was clean and comfortable, and the staff was friendly and helpful. We also really enjoyed the bar and the overall atmosphere of the property. It was a great place for our family vacation, and we would definitely stay here again."

Opal Sands Resort

8/10 Good

"Wonderful views of sunsets over the gulf from the balcony! Our room and the property including the pool were kept very clean. The only reason I am not giving it 5 stars is because there was incessant, very loud pop music playing from the pool and bar area. It was loud all the way up to our room on the fourth floor until at least 10:00 p.m., starting at least at least 5:00 p.m.. We could hear it even inside the room with the door closed. I feel like many people would prefer to have a more relaxing time watching sunsets, not listening to screaming loud pop pop rock music while doing so. I had nothing against the music in general, but it was too loud and overdone. Otherwise, lovely place to stay!"

RumFish Beach at TradeWinds

10/10 Excellent

"Our rooms were clean and comfortable and loved the upgrade with a balcony. I loved the little coffee/breakfast bar. Staff was so very helpful and went out of their way to answer any questions and help us. The only thing questionable was the creamer in my room for coffee. It was rock solid and very stale."

Hotels in Diamond Isle, St. Petersburg - Clearwater

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Diamond Isle hotels

1. Fairfield Inn & Suites by Marriott Clearwater Beach

2. Pier House 60 Clearwater Beach Marina Hotel

3. Comfort Suites Clearwater - Dunedin

4. Hyatt Regency Clearwater Beach Resort and Suites

5. ChartHouse Clearwater Beach Marina Hotel

6. Residence Inn by Marriott Clearwater Downtown

7. Devon Shores

8. SpringHill Suites by Marriott Clearwater Beach

9. CW Resort

10. Wyndham Grand Clearwater Beach

11. Holiday Inn & Suites Clearwater Beach by IHG

12. AC Hotel Clearwater Beach

13. Edge Hotel Clearwater Beach

14. Clearwater Beach Hotel

15. Holiday Inn Express Hotel & Suites Clearwater North-Dunedin by IHG

16. Gulfview Hotel on the Beach

17. Dolphin Sands Clearwater Beach, an Ascend Collection Hotel

18. Hampton Inn & Suites Clearwater Beach

19. The Grant Street Inn Dunedin Downtown Historic District, an Ascend Collection Hotel

20. La Quinta Inn by Wyndham Clearwater Central

Where to stay in Diamond Isle

Downtown St. Petersburg

Pass-a-Grille

Sand Key

Sunset Beach

Don Cesar

Top Diamond Isle Hotel Reviews

Hilton Clearwater Beach Resort & Spa

Frequently asked questions

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