Diamond Isle Holidays

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Our guide on 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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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

Our pick of the best Diamond Isle Hotel Deals

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 NZ$405 per night from 1 Oct to 2 Oct
NZ$405
1 Oct - 2 Oct
includes taxes & fees
8.2/10 Very Good! (1,437 reviews)
"It was nice and relaxing and right in the beach! The interior is a little dated but comfortable. We had everything we needed in the little kitchenette. I wish we could have stayed longer. The beds are very comfy!"

Reviewed on 15 Sept 2025

RumFish Beach at TradeWinds
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 NZ$388 per night from 24 Sept to 25 Sept
NZ$388
24 Sept - 25 Sept
includes taxes & fees
8/10 Very Good! (2,192 reviews)
"This was our second stay at the Hilton Clearwater. The location is perfect. No need for a car. Shopping, dining and close to the harbor if you decide to go on a dinner cruise. The private beach was beautiful. The hotel was clean and had been updated. We will definitely visit again!"

Reviewed on 15 Sept 2025

Hilton Clearwater Beach Resort & Spa
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 NZ$399 per night from 19 Sept to 20 Sept
NZ$399
19 Sept - 20 Sept
includes taxes & fees
9/10 Wonderful! (1,062 reviews)
"Front desk was so helpful and made check in a breeze. We had dampness and a stuck tub/shower lever. They were thoughtful by dropping the resort fee. Parking is $30/day."

Reviewed on 14 Sept 2025

Grand Hyatt Tampa Bay
See all 13,094 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.

Discover the most popular places to visit in Diamond Isle

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

John's Pass Village & Boardwalk
Tropicana Field

Tropicana Field

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the top-notch restaurants while you're in the area.

Tropicana Field
Salvador Dali Museum featuring night scenes and modern architecture

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

Activities

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

NZ$54
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

NZ$59
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

NZ$63
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
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.