Diamond Isle Holidays

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    Save up to €900 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

2.5 out of 5
Price was €396, price is now €329 per person
€329
per person
16 Sept - 20 Sept
found 19 hours ago
Return flight included
New York (JFK) to Tampa (TPA)
9.4/10 Exceptional! (1,294 reviews)

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was €605, price is now €464 per person
€464
per person
16 Sept - 20 Sept
found 19 hours ago
Return flight included
New York (JFK) to Tampa (TPA)
8/10 Very good! (142 reviews)

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Price was €560, price is now €470 per person
€470
per person
16 Sept - 20 Sept
found 19 hours ago
Return flight included
New York (JFK) to Tampa (TPA)
8.6/10 Excellent! (2,722 reviews)
The hotel is in a great location and the staff was superb. The part I did not like was the floor and the room. The floor was the 8th. The colors are horrible, bright yellow and bright darker blue, which the corners were not even trimmed properly, it wouldn't matter anyway since the colors were not appealing at all. Now the room was ok, except for the old carpet and the stuffy smell, you'll get over it after being there for a little while. I would not stay there again though. If you are about location the hotel will do it. Thanks to the staff for being so nice.

Reviewed on 29 Jul 2026

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

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.

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 €287 per night from 9 Aug to 10 Aug
€287
9 Aug - 10 Aug
includes taxes & fees
9.4/10 Exceptional! (3,609 reviews)
"Great Family environment. All things to do in walking distance."

Reviewed on 29 Jul 2026

Wyndham Grand Clearwater Beach
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
The price is €146 per night from 2 Aug to 3 Aug
€146
2 Aug - 3 Aug
includes taxes & fees
The Westin Tampa Bay
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 €216 per night from 9 Aug to 10 Aug
€216
9 Aug - 10 Aug
includes taxes & fees
8.2/10 Very good! (2,849 reviews)
"There is a daily charge of $40 daily for valet parking that is mandatory and non negotiable. This is not included in your booking."

Reviewed on 29 Jul 2026

Hilton Clearwater Beach Resort & Spa
See all 13,834 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 €329, 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

Starlite Infinity Evening Yacht Cruise Clearwater

Starlite Infinity Evening Yacht Cruise Clearwater

€32
per adult
90% of travellers recommend
Starlite Infinity Evening Yacht Cruise Clearwater
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

€68
per adult
100% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

€43
per adult
94% of travellers recommend
Pirate Adventure Cruise - John's Pass
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.