Diamond Isle Vacations from ￥258,889

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The Latest Diamond Isle Vacation Packages

Price found within the past 48 hours. Click for updated prices.
EVEN Hotel Sarasota-Lakewood Ranch by IHG

EVEN Hotel Sarasota-Lakewood Ranch by IHG

3.5 out of 5
per person
Aug 21 - Aug 27
found 13 hours ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
8.4/10 Very Good! (994 reviews)
Hidden gem! Excellent service

Reviewed on Jul 2, 2025

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
per person
Aug 21 - Aug 27
found 13 hours ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
8.6/10 Excellent! (2,137 reviews)
Espectacular el lugar lo único que no nos gustó que la piscina la cierran temprano en tiempo de verano deberían cerrarla a las 10 pm

Reviewed on Jul 6, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
per person
Aug 21 - Aug 27
found 13 hours ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
9.2/10 Wonderful! (1,008 reviews)
The staff were very helpful and friendly.

Reviewed on Jul 4, 2025

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
per person
Aug 21 - Aug 27
found 13 hours ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
9/10 Wonderful! (1,013 reviews)
Great location wonderful staff clean rooms

Reviewed on Jul 7, 2025

Carlisle Inn

Carlisle Inn

3.5 out of 5
Pinecraft
per person
Aug 21 - Aug 27
found 13 hours ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
10/10 Exceptional! (1,868 reviews)
We had such an amazing experience here. We will definitely be back again.

Reviewed on Jul 6, 2025

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

5/5(26 area reviews)

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

Hilton Clearwater Beach Resort & Spa
Hilton Clearwater Beach Resort & Spa
4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is ￥28,124 per night from Jul 14 to Jul 15
￥28,124
￥37,493 total
Jul 14 - Jul 15
includes taxes & fees
8/10 Very Good! (1,979 reviews)
"Had a great stay. Easy to get around to restaurants and stores in foot."

Reviewed on Jul 5, 2025

Hilton Clearwater Beach Resort & Spa
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 ￥36,869 per night from Aug 3 to Aug 4
￥36,869
￥47,376 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (2,350 reviews)
"The entire hotel staff was amazing from front desk,pool staff,restaurants and the maids."

Reviewed on Jul 4, 2025

Wyndham Grand Clearwater Beach
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4 out of 5
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is ￥21,844 per night from Aug 3 to Aug 4
￥21,844
￥24,793 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (1,638 reviews)
"Very beautiful"

Reviewed on Jul 5, 2025

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
See all 12,849 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 vacation package cost?
Starting from a low ￥258,889, 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

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(1,625 reviews)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area, or check out its lively bars.

John's Pass Village & Boardwalk
Tropicana Field

Tropicana Field

4.5/5(591 reviews)

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the lively bars while you're in the area.

Tropicana Field
Fort De Soto Park which includes a sandy beach

Fort De Soto Park

4.5/5(676 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

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

￥4,636
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

￥5,352
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
Sea Screamer boat in Orlando

Day Trip to Clearwater Beach with Sea Screamer Ride

￥18,073
per adult
90% of travellers recommend
Day Trip to Clearwater Beach with Sea Screamer Ride
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.