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
A beach with people, a city skyline, and a distinctive pink building.

Pass-a-Grille

1 out of top 10 points of interest in this area
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 St. Petersburg - Clearwater Beaches or Gulf Beaches Historical Museum.

Find hotels in Pass-a-Grille

Top hotels in Diamond Isle

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 6.640.328 ₫ per night from 2 Aug to 3 Aug
6.640.328 ₫
8.543.199 ₫ total
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (3,463 reviews)
"😊"

Reviewed on 3 Jul 2026

Wyndham Grand Clearwater Beach
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
The price is 5.382.615 ₫ per night from 14 Jul to 15 Jul
5.382.615 ₫
7.121.962 ₫ total
14 Jul - 15 Jul
includes taxes & fees
8.2/10 Very good! (2,752 reviews)
"I always love to stay at Hilton properties because I know they take care of their guests, but this was not true here. We arrived at the property at 7pm. Check in is 4. I was told that our room was not ready yet, they were fixing a light. It should only be 15 minutes. The man at check-in told me that ..."

Reviewed on 3 Jul 2026

Hilton Clearwater Beach Resort & Spa
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 4.708.539 ₫ per night from 9 Jul to 10 Jul
4.708.539 ₫
6.954.573 ₫ total
9 Jul - 10 Jul
includes taxes & fees
8.2/10 Very good! (2,095 reviews)
"Beach staff was great, pool staff and games were fun!"

Reviewed on 3 Jul 2026

RumFish Beach at TradeWinds
See all 13,790 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.