Diamond Isle Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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

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    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
Downtown St. Petersburg featuring outdoor art

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

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
The price is S$536 per night from 22 Feb to 23 Feb
S$536
22 Feb - 23 Feb
includes taxes & fees
9.2/10 Wonderful! (3,027 reviews)
A perfect stay.

Reviewed on 11 Feb, 2026

Wyndham Grand Clearwater Beach
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
1200 N Westshore Blvd Tampa FL
The price is S$106 per night from 8 Mar to 9 Mar
S$106
8 Mar - 9 Mar
includes taxes & fees
6.2/10 (3,942 reviews)
Mucha limpieza y descanso pleno

Reviewed on 10 Feb, 2026

Ramada by Wyndham Tampa Westshore Airport South
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 S$381 per night from 16 Feb to 17 Feb
S$381
16 Feb - 17 Feb
includes taxes & fees
8.2/10 Very Good! (1,626 reviews)
The resort was excellent. Access to all activities restaurants beach pool etc was really nice. Staff was about half and half. Some excelled - the beach personnel and the front desk personnel were extremely helpful and excellent. The room was very clean and quiet although small.

Reviewed on 13 Feb, 2026

RumFish Beach at TradeWinds
See all 13,441 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

Salvador Dali Museum showing 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
Sand Key Park showing general coastal views and a sandy beach

Sand Key Park

If a restful holiday is part of your travel plans, Sand Key Park might be the perfect place to visit during your trip to Clearwater Beach. Stroll along the clear-water beaches in this family-friendly area or visit its top-notch restaurants.

Sand Key Park

Splash Harbour Water Park

Bring the children to Splash Harbour Water Park and enjoy some excitement at this theme park in Indian Rocks Beach. While you're in the area, stroll along the beautiful beaches.

Splash Harbour Water Park

Things to do

The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

S$47
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

S$47
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Picture 4 for Activity Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

S$70
per adult
100% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
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.