Diamond Isle Holidays

  • Plan, book, travel with confidence

    • Better together

    Save up to €185 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
Default Image

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.

Find hotels in Downtown St. Petersburg

Top hotels in Diamond Isle

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 €209 per night from 20 Oct to 21 Oct
€209
20 Oct - 21 Oct
includes taxes & fees
8/10 Very Good! (2,239 reviews)
"Staff was very friendly and caring of our needs and wants. The hotel was clean inside and out. The pool area was clean but the floor tiles were uneven and slippery. The pool bar staff was friendly and very accommodating."

Reviewed on 10 Oct 2025

Hilton Clearwater Beach Resort & Spa
DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
3050 N Rocky Point Dr W, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is €75 per night from 26 Oct to 27 Oct
€75
26 Oct - 27 Oct
includes taxes & fees
8/10 Very Good! (1,008 reviews)
"The room was clean; however, the bathroom is dated."

Reviewed on 9 Oct 2025

DoubleTree by Hilton Tampa Rocky Point Waterfront
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 €238 per night from 19 Oct to 20 Oct
€238
19 Oct - 20 Oct
includes taxes & fees
9.4/10 Exceptional! (2,709 reviews)
"Ocean Hai was absolutely terrible. The food didn't resemble Asian food whatsoever and was very overpriced. I would not recommend to anyone nor would I ever go back!"

Reviewed on 10 Oct 2025

Wyndham Grand Clearwater Beach
See all 13,137 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.

Popular places to visit

John's Pass Village & Boardwalk

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 beautiful beaches in this family-friendly area or visit its top-notch restaurants.

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

Fort De Soto Park

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

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

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

Things to do

The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

€32
per adult
88% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

€30
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
Guaranteed Dolphin Sighting Tour on Tropics Boat Tours

Guaranteed Dolphin Sighting Tour on Tropics Boat Tours

€32
per adult
94% of travellers recommend
Guaranteed Dolphin Sighting Tour on Tropics Boat Tours
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.