Diamond Isle Vacations

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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
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

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is NT$6,017 per night from Apr 12 to Apr 13
NT$6,017
NT$8,787 total
Apr 12 - Apr 13
includes taxes & fees
8.2/10 Very Good! (1,749 reviews)
Accommodations were nice. The room was big and clean, the property is clean, staff is friendly. Beach area clean, lots of restaurants on the property.

Reviewed on 2026/4/2

RumFish Beach at TradeWinds
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
The price is NT$12,208 per night from May 3 to May 4
NT$12,208
NT$15,060 total
May 3 - May 4
includes taxes & fees
9.4/10 Exceptional! (3,106 reviews)
Fr a distraction free, lovely environment to vacation, wyndham Grand Clearwater is the best, Staff, hotel, proximity to activities is all you could wish for. The spa is beyond OUTSTANDING for quality of services.

Reviewed on 2026/4/3

Wyndham Grand Clearwater Beach
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 NT$9,592 per night from Apr 14 to Apr 15
NT$9,592
NT$12,104 total
Apr 14 - Apr 15
includes taxes & fees
8.2/10 Very Good! (2,521 reviews)
The hotel is in an excellent location. It could really use an update to the rooms.

Reviewed on 2026/4/2

Hilton Clearwater Beach Resort & Spa
See all 13,651 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

Aerial view of the pink-tinged waters reflecting the vibrant sunset hues next to the John's Pass Village & Boardwalk, Treasure Island, Florida, United States.

John's Pass Village & Boardwalk

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Vinoy Park

Vinoy Park

While area beaches are abundant, it’s convenient to have this lovely spot right in the city. Lounge under a palm tree and enjoy the frequent entertainment.

Vinoy Park
Salvador Dali Museum

Salvador Dali Museum

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.