Diamond Isle Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Diamond Isle
Price found within the past 48 hours. Click for updated prices.
Westwinds Waterfront Resort
CA $1,084
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (737 reviews)
Excellent time at this property. Only thing I wish was a little bit later checkout time as our flight wasn’t until 9pm at night and we had to be out by 10am. I understand it was most likely due to cleaning for incoming guest so we made it work. Overall I would definitely stay at this property again if we ever returned to Clearwater.
Reviewed on Oct 15, 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
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.
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.
Sand Key
1 out of top 10 points of interest in this area
While visiting Sand Key, you might make a stop by sights like Belleair Beach and Sand Key Park.
Sunset Beach
Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like Sunset Beach and St. Petersburg - Clearwater Beaches.
Sunshine Beach
If you're spending some time in Sunshine Beach, St. Petersburg - Clearwater Beaches and St. Petersburg Municipal Beach at Treasure Island are top sights worth seeing.
Diamond Isle Hotel Deals
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $290
CA $383 total
Oct 29 - Oct 30
includes taxes & fees
9.4/10 Exceptional! (3,992 reviews)
"The Wyndham Grand is a really nice hotel! Staff are all very nice and helpful. The rooms are spacious and clean. It’s also in a great location close to everything."
Reviewed on Oct 18, 2026
Hyatt Regency Clearwater Beach Resort and Suites
301 S Gulfview Blvd Clearwater Beach FL
CA $336
CA $436 total
Oct 19 - Oct 20
includes taxes & fees
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
CA $219
CA $249 total
Oct 25 - Oct 26
includes taxes & fees
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 vacation package cost?
Starting from a low CA $953, 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
Starlite Infinity Evening Yacht Cruise Clearwater
CA $51
per adult
90% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
CA $39
per adult
94% of travellers recommend
Dolphin Racer Speedboat Adventure
CA $50
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.