Diamond Isle Vacation Packages

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Diamond Isle

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,152, price is now CA $732 per person
CA $732
per person
Mar 26 - Mar 31
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Older property but very well maintained. It was clean and had everything we needed for our stay. Great communication with the host.

Reviewed on Feb 10, 2026

The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Price was CA $1,306, price is now CA $835 per person
CA $835
per person
May 10 - May 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.2/10 Very Good! (515 reviews)
All of those and the wonderful, helpful staff

Reviewed on Feb 19, 2026

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Town 'n' Country
Price was CA $1,855, price is now CA $1,189 per person
CA $1,189
per person
Apr 14 - Apr 21
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Tampa (TPA)
2/10 (4 reviews)
Arvilla

Arvilla

2 out of 5
Sunshine Beach
Price was CA $1,754, price is now CA $1,147 per person
CA $1,147
per person
Apr 6 - Apr 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
7.2/10 Good! (24 reviews)
It was clean but small. Quiet atmosphere

Reviewed on Feb 23, 2026

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was CA $1,366, price is now CA $894 per person
CA $894
per person
Apr 7 - Apr 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
Staff are polite and efficient. Nice pool. Overall a nice hotel close to airport.

Reviewed on Feb 22, 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 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

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 $487 per night from Feb 26 to Feb 27
CA $487
CA $604 total
Feb 26 - Feb 27
includes taxes & fees
9.2/10 Wonderful! (3,028 reviews)
The hotel, staff, room was amazing!

Reviewed on Feb 18, 2026

Wyndham Grand Clearwater Beach
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 $324 per night from Feb 24 to Feb 25
CA $324
CA $452 total
Feb 24 - Feb 25
includes taxes & fees
8.2/10 Very Good! (1,637 reviews)
The staff was friendly and helpful. The room was worn and dated - cracked bathroom floor, leaky bathroom sink faucet, low sh. ower pressure, dusty couch with very worn arms. Food/drinks are very expensive. Many amenities worn and broken.

Reviewed on Feb 17, 2026

RumFish Beach at TradeWinds
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
The price is CA $278 per night from Mar 8 to Mar 9
CA $278
CA $315 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (1,139 reviews)
Clean rooms very helpful stafff. Will stay again

Reviewed on Feb 22, 2026

The Westin Tampa Bay
See all 13,464 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Diamond Isle vacation package cost?
Starting from a low CA $732, 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.

Discover the most popular places to visit in Diamond Isle

Florida. Madeira Beach Florida. Gulf of Mexico or ocean beach, Hotels and Resorts. John's Pass Village and Boardwalk. Turquoise color of salt water. American shore. Summer or Autumn vacation.

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 check out its top-notch restaurants.

John's Pass Village & Boardwalk
White sand and palm trees in Clearwater beach

Clearwater Beach

Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach
Vinoy Park

Vinoy Park

While area beaches are abundant, it’s convenient to have this lovely spot right in the city. Lounge under a palm tree and enjoy the frequent entertainment.

Vinoy Park

Things to do

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $50
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

CA $51
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
Picture 4 for Activity Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

CA $75
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.