Diamond Isle Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Top Holiday Package Deals in Diamond Isle

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $1,494, price is now CA $968 per person
CA $968
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,206 reviews)
The front desk agent made our check in so easy. Hotel is very close to the beach and amenities were great. 10/10 can’t wait to be back!

Reviewed on Jul 7, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,427, price is now CA $1,601 per person
CA $1,601
per person
Sep 23 - Sep 30
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (1,057 reviews)
There was a problem with the toilet in the master bedroom running all night, both nights. They tried to fix it but was unsuccessful for both nights.

Reviewed on Jul 9, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $1,932, price is now CA $1,333 per person
CA $1,333
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews
We had such a great stay at the CW Resort in Clearwater! The pool area was beautiful and relaxing, the views were amazing, and the entire property was very clean and well maintained. It was the perfect place to unwind and enjoy a Florida getaway. We would definitely stay here again!

Reviewed on Jul 8, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $1,755, price is now CA $1,244 per person
CA $1,244
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (564 reviews)
If you are thinking of booking the Avalon club it is definitely worth it I highly recommend

Reviewed on Jul 8, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,054, price is now CA $1,471 per person
CA $1,471
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (543 reviews)
Easy check in and out and staff was awesome. Love this place

Reviewed on Jul 8, 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

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotels in Pass-a-Grille

Diamond Isle Hotel Deals

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 CA $355 per night from Aug 2 to Aug 3
CA $355
CA $457 total
Aug 2 - Aug 3
includes taxes & fees
9.4/10 Exceptional! (3,503 reviews)
"It's good hotel but definitely not good for couples lot's of family a ton of kids"

Reviewed on Jul 9, 2026

Wyndham Grand Clearwater Beach
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
The price is CA $270 per night from Aug 9 to Aug 10
CA $270
CA $361 total
Aug 9 - Aug 10
includes taxes & fees
8.2/10 Very good! (2,799 reviews)
"THERE WERE HIDDEN FEES THAT WERE REQUIRED AT CHECK IN, THE VALET WAS MANDITORY WHICH WERE 40 A DAY AN YOU HAD NO CHOICE IN THE MATTER. THE PHONE DID NOT WORK SO I COULDNT CALL DOWN TO THE FRONT DESK WHEN THINGS WERE NEEDED, HOUSEKEEPING IS NOT CLEAN UNTIL AFTER 5 AND DIDNT RESTOCK THE TOILET ..."

Reviewed on Jul 9, 2026

Hilton Clearwater Beach Resort & Spa
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 CA $254 per night from Aug 9 to Aug 10
CA $254
CA $375 total
Aug 9 - Aug 10
includes taxes & fees
8.2/10 Very good! (2,128 reviews)
"My first night I had to deal with kids knocking on my door and running multiple times after dark. Not a very pleasant experience. As far as the room. Convenient being walking distance to the beach and having the chairs available. (As long as you get there early) The front desk employee when checking ..."

Reviewed on Jul 9, 2026

RumFish Beach at TradeWinds
See all 13,784 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.
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Frequently asked questions

How much does a Diamond Isle vacation package cost?
Starting from a low CA $968, 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 vacation.
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 traveler favorites.
How far in advance should I book my Diamond Isle vacation?
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 vacation package?
Yes, you're in charge. Expedia has access to more than 550 airlines around the world, so you can design your Diamond Isle vacation according to your budget and travel needs.
If I'm not able to travel, can I cancel my Diamond Isle vacation package?
Your situation can change without warning, so yes, you can. You may be able to cancel and rebook your Diamond Isle vacation 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

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $53
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
Starlite Infinity Evening Yacht Cruise Clearwater

Starlite Infinity Evening Yacht Cruise Clearwater

CA $52
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

CA $95
per adult
100% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
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.