Diamond Isle Holidays

Book a Hotel + Flight or Car together to unlock savings

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
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Pass-a-Grille

5/5(3 area reviews)

Pass-a-Grille is popular for its beaches, and if you're looking for more to see and do, you might think about a trip to Pass-a-Grille Beach or St. Petersburg - Clearwater Beaches.

Find hotels in Pass-a-Grille

Top hotels in Diamond Isle

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 3.551.974 ₫ per night from 24 Aug to 25 Aug
3.551.974 ₫
5.646.535 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,363 reviews)
"Plenty of food options, comfortable and clean."

Reviewed on 17 Aug 2025

RumFish Beach at TradeWinds
Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

4 out of 5
2900 Bayport Drive, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is 4.468.867 ₫ per night from 24 Aug to 25 Aug
4.468.867 ₫
5.966.725 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,019 reviews)
"Great time"

Reviewed on 14 Aug 2025

Grand Hyatt Tampa Bay
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy, Tampa, FL
Fully refundable
The price is 4.108.941 ₫ per night from 31 Aug to 1 Sept
4.108.941 ₫
4.663.648 ₫ total
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Great hotel"

Reviewed on 12 Aug 2025

The Westin Tampa Bay
See all 12,905 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 holiday 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 1null000null000 properties across the globe, which lets you customize your Diamond Isle holiday.
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 traveller favourites.
How far in advance should I book my Diamond Isle holiday?
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 holiday package?
Yes, you're in charge. Expedia has access to more than 550 airlines around the world, so you can design your Diamond Isle holiday according to your budget and travel needs.
If I'm not able to travel, can I cancel my Diamond Isle holiday package?
Your situation can change without warning, so yes, you can. You may be able to cancel and rebook your Diamond Isle holiday 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.

Popular places to visit

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4/5(33 reviews)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the beautiful beaches in this family-friendly area or visit its lively bars.

John's Pass Village & Boardwalk
Fort De Soto Park featuring a beach

Fort De Soto Park

4.5/5(25 reviews)

Enjoy the beautiful sunsets and explore Fort De Soto Park, a lovely green space in Tierra Verde. Discover the top-notch restaurants and great live music in this family-friendly area.

Fort De Soto Park
Salvador Dali Museum featuring night scenes and modern architecture

Salvador Dali Museum

5/5(20 reviews)

You can spend time browsing the exhibits at Salvador Dali Museum during your trip to St. Petersburg. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Salvador Dali Museum