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

One Key™ —Expedia’s free travel rewards program—gives you instant access to discounts with Member Prices on Diamond Isle hotels. Plus, you’ll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Diamond Isle?

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.

Diamond Isle Hotels: Cheap Accommodation in Diamond Isle

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

Tami

includes taxes & fees

18 Aug - 19 Aug

Outdoor pool, pool umbrellas, pool loungers

2. Wyndham Grand Clearwater Beach

1.6 km from Diamond Isle

Keishaw

includes taxes & fees

23 Aug - 24 Aug

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

3. Hyatt Regency Clearwater Beach Resort and Suites

1.8 km from Diamond Isle

James

includes taxes & fees

17 Aug - 18 Aug

4. Comfort Suites Clearwater - Dunedin

2.6 km from Diamond Isle

Mark

includes taxes & fees

9 Aug - 10 Aug

5. ChartHouse Clearwater Beach Marina Hotel

1.6 km from Diamond Isle

Susan

includes taxes & fees

6 Aug - 7 Aug

6. Pier House 60 Clearwater Beach Marina Hotel

1.6 km from Diamond Isle

John

includes taxes & fees

10 Aug - 11 Aug

7. Residence Inn by Marriott Clearwater Downtown

3.9 km from Diamond Isle

Ashley

includes taxes & fees

10 Aug - 11 Aug

8. Holiday Inn & Suites Clearwater Beach by IHG

2.4 km from Diamond Isle

Jonathan

includes taxes & fees

17 Aug - 18 Aug

9. Devon Shores

1.9 km from Diamond Isle

Iris

includes taxes & fees

10 Aug - 11 Aug

10. Best Western Plus Yacht Harbor Inn

3.9 km from Diamond Isle

Diane

includes taxes & fees

3 Aug - 4 Aug

11. Ivory Sands Beach Suites

2.2 km from Diamond Isle

Alejandro

includes taxes & fees

5 Aug - 6 Aug

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

4.3 km from Diamond Isle

Scott

includes taxes & fees

28 Aug - 29 Aug

13. Clearwater Beach Hotel

2.3 km from Diamond Isle

Shawana

includes taxes & fees

13 Aug - 14 Aug

Outdoor pool, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)

14. Hampton Inn & Suites Clearwater Beach

2.4 km from Diamond Isle

Karla

includes taxes & fees

17 Aug - 18 Aug

Desk, blackout curtains, iron/ironing board, free cots/infant beds

15. Dolphin Sands Clearwater Beach, an Ascend Collection Hotel

2.5 km from Diamond Isle

george

includes taxes & fees

18 Aug - 19 Aug

16. Edge Hotel Clearwater Beach

2.3 km from Diamond Isle

Leonardo Javier

includes taxes & fees

2 Aug - 3 Aug

17. Gulfview Hotel on the Beach

2.4 km from Diamond Isle

NESIM

includes taxes & fees

4 Aug - 5 Aug

18. Pelican Pointe Clearwater Beach Hotel

2.2 km from Diamond Isle

kimberly

includes taxes & fees

16 Aug - 17 Aug

Outdoor pool, pool cabanas (surcharge), pool umbrellas

19. Clearwater Beach Marriott Resort on Sand Key

Sand Key, 3.9 km from Diamond Isle

Jackie

includes taxes & fees

11 Aug - 12 Aug

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

4.3 km from Diamond Isle

Philip

includes taxes & fees

4 Aug - 5 Aug

View all properties

Our guide on where to stay in Diamond Isle

Find the best Diamond Isle areas for the activities you enjoy most.

A sandy beach with dunes and a clear sky.

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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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 red lifeguard tower on a sandy beach with a clear blue sky.

Sand Key

If you're spending some time in Sand Key, St. Petersburg - Clearwater Beaches and Sand Key Park are top sights worth seeing.

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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 St. Petersburg - Clearwater Beaches and Sunset Beach.

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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 Gulf Beaches Historical Museum and Splash Island Water Park are two attractions nearby that you can check out.

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Top Diamond Isle Hotel Reviews

Recent Reviews in Diamond Isle

JW Marriott Clearwater Beach Resort & Spa

10/10 Excellent

"This hotel is wonderful! You can’t beat the private beach and beautiful rooftop pool. The rooms are spacious and clean. The beds were comfortable. The hotel is beautiful and well maintained. This was our second stay and we will definitely be back."

Clearwater Beach Marriott Resort on Sand Key

10/10 Excellent

"The pool area is terrific, great chairs and sun deck, pool temp was just right, very nice bathrooms and easy to get to from the pool area, accommodated quite a few people without feeling crowded. The workout facility was small but nice equipment. The room was a great size and allowed us to have plenty of space for our things, pool view and balcony were a nice touch, strange having to walk outside to room but worked out fine."

Diamond Isle Hotels, St. Petersburg - Clearwater

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Our top choices for Diamond Isle hotels

1. Fairfield Inn & Suites by Marriott Clearwater Beach

2. Wyndham Grand Clearwater Beach

3. Hyatt Regency Clearwater Beach Resort and Suites

4. Comfort Suites Clearwater - Dunedin

5. ChartHouse Clearwater Beach Marina Hotel

6. Pier House 60 Clearwater Beach Marina Hotel

7. Residence Inn by Marriott Clearwater Downtown

8. Holiday Inn & Suites Clearwater Beach by IHG

9. Devon Shores

10. Best Western Plus Yacht Harbor Inn

11. Ivory Sands Beach Suites

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

13. Clearwater Beach Hotel

14. Hampton Inn & Suites Clearwater Beach

15. Dolphin Sands Clearwater Beach, an Ascend Collection Hotel

16. Edge Hotel Clearwater Beach

17. Gulfview Hotel on the Beach

18. Pelican Pointe Clearwater Beach Hotel

19. Clearwater Beach Marriott Resort on Sand Key

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

Our guide on where to stay in Diamond Isle

Pass-a-Grille

Downtown St. Petersburg

Sand Key

Sunset Beach

Don Cesar

Top Diamond Isle Hotel Reviews

Recent Reviews in Diamond Isle

JW Marriott Clearwater Beach Resort & Spa

Frequently asked questions

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