Diamond Isle Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

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

  • 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
A modern plaza with a large sculpture, palm trees, and a high-rise building in the background.

Downtown St. Petersburg

1 out of top 10 points of interest in this area

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

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 beach with a rainbow over the ocean.

Sand Key

1 out of top 10 points of interest in this area

If you're spending some time in Sand Key, Belleair Beach and Sand Key Park are top sights worth seeing.

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A beach with people walking along the shore, waves crashing onto the sand, and a city skyline in the background.

Sunset Beach

Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like Sunset Beach and St. Petersburg Municipal Beach at Treasure Island.

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A sunset over the ocean with a person paddleboarding and a floating structure.

Sunshine Beach

While visiting Sunshine Beach, you might make a stop by sights like St. Petersburg Municipal Beach at Treasure Island and St. Petersburg - Clearwater Beaches.

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Top hotels in Diamond Isle

The Westin Tampa Bay

The Westin Tampa Bay

7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
S$223
14 Sept - 15 Sept
includes taxes & fees
The Westin Tampa Bay
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
S$361
15 Sept - 16 Sept
includes taxes & fees
9.4/10 Exceptional! (3,871 reviews)
"Yuli and the andrews at the bar rule so hard; nicest people ever. Same with, Olivia, at ocean hai in the hotel restaurant and Evan at the front reception desk — it’s hard to find kind, genuine people in the world and they all left an impact on me that would make me want to come back again :)"

Reviewed on 12 Sept, 2026

Wyndham Grand Clearwater Beach
Hyatt Regency Clearwater Beach Resort and Suites

Hyatt Regency Clearwater Beach Resort and Suites

301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
S$402
1 Oct - 2 Oct
includes taxes & fees
9.4/10 Exceptional! (2,343 reviews)
"A"

Reviewed on 12 Sept, 2026

Hyatt Regency Clearwater Beach Resort and Suites
See all 13,931 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 1,000,000 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.

Things to do

Mega Bite II

Mega Bite Dolphin Tour Boat in Clearwater Beach

S$36
per adult
96% of travellers recommend
Mega Bite Dolphin Tour Boat in Clearwater Beach
Starlite Infinity Evening Yacht Cruise Clearwater

Starlite Infinity Evening Yacht Cruise Clearwater

S$47
per adult
90% of travellers recommend
Starlite Infinity Evening Yacht Cruise Clearwater
Suncoast Sailing's Sunset Sailing Experience!

Suncoast Sailing's Sunset Sailing Experience!

S$90
per adult
98% of travellers recommend
Suncoast Sailing's Sunset Sailing Experience!
See all activities in St. Petersburg - Clearwater

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.