Diamond Isle Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

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
Pass-a-Grille

Pass-a-Grille

5/5(26 area reviews)

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.

Find hotels in Pass-a-Grille

Diamond Isle Hotel Deals

Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is ₩257,438 per night from Aug 11 to Aug 12
₩257,438
₩345,600 total
Aug 11 - Aug 12
includes taxes & fees
8/10 Very Good! (2,002 reviews)
"Great resort"

Reviewed on Jul 12, 2025

Hilton Clearwater Beach Resort & Spa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is ₩209,103 per night from Aug 7 to Aug 8
₩209,103
₩237,333 total
Aug 7 - Aug 8
includes taxes & fees
8.6/10 Excellent! (1,654 reviews)
"Nice overnight stay! Super comfortable"

Reviewed on Jul 12, 2025

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is ₩380,419 per night from Aug 4 to Aug 5
₩380,419
₩484,570 total
Aug 4 - Aug 5
includes taxes & fees
9.2/10 Wonderful! (2,375 reviews)
"Great location with convenient stores, restaurants,very clean the hotel with excellent guest service. Overall everything was great at our stay."

Reviewed on Jul 13, 2025

Wyndham Grand Clearwater Beach
See all 12,902 properties in Diamond Isle
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Diamond Isle vacation package cost?
Starting from a low , a package is your gateway to low-priced travel. Custom make your Diamond Isle getaway by picking from our wide range of airfares, hotels and rental cars.
How do I get a cheap travel package to Diamond Isle?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and rental cars --- we've got them all covered. Select a combination that suits you and see your savings grow. Of course, a travel package is never one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 properties across the globe, which lets you customize your Diamond Isle vacation.
Where should I stay in Diamond Isle?
Make sightseeing easier by staying in a hotel within walking distance of Diamond Isle's iconic attractions. Clearwater Marine Aquarium and Sand Key Park are two traveler favorites.
How far in advance should I book my Diamond Isle vacation?
Search Expedia to compare international fares as soon as you know your travel dates. You can generally purchase a ticket up to a year prior to departure. If you don't see your preferred air carrier, or you've left things to the last minute, don't stress. Low prices to Diamond Isle occasionally appear a few weeks before departure.
What does an Expedia Diamond Isle travel package include?
Much of that depends on you. You can select from a range of Diamond Isle bundles, such as a hotel, flight and rental car. You can also book a flight and a hotel, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your dream Diamond Isle trip looks like, you're sure to save!
What should I know before booking a Diamond Isle travel package?
You can save a tidy sum by combining your hotels, airfares and rental cars. Once you've made your booking, you can add on things like activities or sightseeing tours. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with a Diamond Isle Expedia vacation package?
Yes, you're in charge. Expedia has access to more than 550 airlines around the world, so you can design your Diamond Isle vacation according to your budget and travel needs.
If I'm not able to travel, can I cancel my Diamond Isle vacation package?
Your situation can change without warning, so yes, you can. You may be able to cancel and rebook your Diamond Isle vacation package at no cost if you've booked in the last 24 hours. For bookings older than that, you can still make changes, but your car rental company, airline or hotel may impose a fee. Looking for more information? Have a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

Discover the most popular places to visit in Diamond Isle

Fort De Soto Park which includes a sandy beach

Fort De Soto Park

4.5/5(676 reviews)

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park
Tropicana Field

Tropicana Field

4.5/5(591 reviews)

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the lively bars while you're in the area.

Tropicana Field
Salvador Dali Museum showing night scenes and modern architecture

Salvador Dali Museum

4.5/5(1,166 reviews)

Browse the surrealistic masterpieces of a world-famous Spanish painter in a remarkable building that perfectly suits the style of the art exhibits.

Salvador Dali Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.