Diamond Isle Vacation Packages

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Top Holiday Package Deals in Diamond Isle

Price found within the past 48 hours. Click for updated prices.
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Aug. 3 - Aug. 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.4/10 Very Good! (1,035 reviews)
From the front desk to the cleaning staff, everyone was helpful and nice. Cleaning staff was always around and kept our room supplied and clean. We had a minor mix up on the room based on accessibility for our 91 year old mom and the front desk made adjustment's and all worked out well. Thank you to the front desk!

Reviewed on May 28, 2024

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Aug. 3 - Aug. 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (297 reviews)
The property was really nice. It was across the street a park that the up-keeping was not that great.

Reviewed on May 27, 2024

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
7.6/10 Good! (1,005 reviews)
As advertised but should inform guest of outside remolding

Reviewed on May 27, 2024

Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Save 100% on your flight
per person
Aug. 3 - Aug. 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.6/10 Excellent! (450 reviews)
The staff was so accommodating and friendly. I was in for two short nights and arrived at the hotel at 2 AM. They let me grab my keys, go to my room to sleep and come back once awoken to fully checkin.

Reviewed on May 13, 2024

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Wesley Chapel South
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
6.8/10 (1,004 reviews)
Beautiful grounds. Rooms were clean and spacious. Would stay here again

Reviewed on May 29, 2024

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
Pass-a-Grille

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 hotel + flight trips in Pass-a-Grille

Diamond Isle Hotel Deals

RumFish Beach Resort by TradeWinds
RumFish Beach Resort by TradeWinds
4 out of 5
6000 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $243 per night from Jun. 9 to Jun. 10
CA $243
CA $360 total
includes taxes & fees
Jun 9 - Jun 10
8.2/10 Very Good! (1,006 reviews)
"Was there on a girl's trip where we just hit the beach and pool so didn't use most of the amenities but there were many available."

Reviewed on May 29, 2024

RumFish Beach Resort by TradeWinds
Sirata Beach Resort
Sirata Beach Resort
3 out of 5
5300 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Jun. 23 to Jun. 24
CA $212
CA $301 total
includes taxes & fees
Jun 23 - Jun 24
7.2/10 Good! (2,245 reviews)
"Excellent"

Reviewed on May 30, 2024

Sirata Beach Resort
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 $305 per night from Jun. 2 to Jun. 3
CA $305
CA $393 total
includes taxes & fees
Jun 2 - Jun 3
9/10 Wonderful! (1,872 reviews)
"We enjoy your stay everything was excellent"

Reviewed on May 31, 2024

Wyndham Grand Clearwater Beach
See all 13,795 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.

Explore other types of vacation packages

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 $554, 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

Image for John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(136 reviews)

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
Image for Tropicana Field

Tropicana Field

4/5(26 reviews)

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
Image for Fort De Soto Park

Fort De Soto Park

4.5/5(28 reviews)

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park

Things to do

Image for StarLite Majesty Evening Yacht Cruise Clearwater

StarLite Majesty Evening Yacht Cruise Clearwater

CA $43
Per adult
86% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Image for 2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

CA $47
Per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
Image for Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

CA $81
Per adult
100% of travellers recommend
Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar
See all activities in St. Petersburg - Clearwater

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.