Diamond Isle Holidays from £720

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Your Diamond Isle Holiday

Experience everything this neighbourhood has to offer with a customized Diamond Isle holiday package. However you picture yourself spending your days here, you'll find countless opportunities for fun, relaxation and adventure. Start your trip to Diamond Isle by visiting nearby attractions such as Clearwater Marine Aquarium, Sand Key Park and Pier 60 Park. Stop dreaming and start doing. When it's time to lock in your next holiday to Diamond Isle, Expedia is here to help.

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

Innisbrook Resort

3.5 out of 5
per person
6 Sept - 13 Sept
found 13 hours ago
Return direct flight included
London (LHR) to Tampa (TPA)
8.2/10 Very Good! (1,001 reviews)
We asked for late check-out twice, and received no response.

Reviewed on 30 Jun 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
18 Aug - 25 Aug
found 1 day ago
Return direct flight included
London (LHR) to Tampa (TPA)
9.6/10 Exceptional! (499 reviews)
We enjoyed the immaculate unit which offered all the amenities that we could possibly ask for. It was tastefully decorated with comfortable furnishings. All the personnel we spoke with were friendly and eager to help with any questions we had. A very enjoyable stay!!

Reviewed on 29 Jun 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
per person
18 Aug - 25 Aug
found 1 day ago
Return direct flight included
London (LHR) to Tampa (TPA)
9.2/10 Wonderful! (1,031 reviews)
The property was quiet, clean and comfortable. The customer service was professional and above average. I would not hesitate to book again. Two bedrooms and two bathrooms, living room and full kitchen was plenty room for husband and I. Only stayed one night but wished it was longer.

Reviewed on 26 Jun 2025

The Avalon Club

The Avalon Club

4 out of 5
per person
7 Aug - 13 Aug
found 1 day ago
Return direct flight included
London (LON) to Tampa (TPA)
9.6/10 Exceptional! (421 reviews)
Everyone was so nice. We really enjoyed how we had such close access to the beach. I think the furniture could use some updating especially in the space we had. Loved our view and will stay there again.

Reviewed on 27 Jun 2025

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
per person
22 Sept - 29 Sept
found 21 hours ago
Return direct flight included
London (LHR) to Tampa (TPA)
8.6/10 Excellent! (2,137 reviews)
Adorable property!! A block away from the bridge to cross over to Siesta Key beach. 7-Eleven 4 minutes away to get ice, beach necessities. Didn't use the pool, but there is parking in front of the rooms. The room itself very comfortable, full kitchen you can cook and it has all items needed to make and serve a meal, full size fridge, good hvac unit to cool the room. Sleeper couch in living room and queen size bed. Super cozy, cute and very comfortable. Would love to return next time we are visiting Siesta Key.

Reviewed on 23 Jun 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
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Pass-a-Grille

5/5(3 area reviews)

As you view this neighborhood’s iconic pink hotel it feels as if you’ve crossed into the past. Find beautiful beaches and serene enjoyment here.

Find hotels in Pass-a-Grille

Top hotels in Diamond Isle

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 £209 per night from 2 Jul to 3 Jul
£209
2 Jul - 3 Jul
includes taxes & fees
8/10 Very Good! (1,963 reviews)
"!!"

Reviewed on 29 Jun 2025

Hilton Clearwater Beach Resort & Spa
Island Grand at TradeWinds
Island Grand at TradeWinds
4 out of 5
5500 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is £196 per night from 7 Jul to 8 Jul
£196
7 Jul - 8 Jul
includes taxes & fees
7.2/10 Good! (1,003 reviews)
"."

Reviewed on 17 Jun 2025

Island Grand at TradeWinds
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 £183 per night from 2 Jul to 3 Jul
£183
2 Jul - 3 Jul
includes taxes & fees
8.2/10 Very Good! (1,282 reviews)
"The beach was crystal clear and very well maintained. They do charge for the first and second rows of the chairs and umbrellas, but the third, fourth and fifth are free. Our first room had a very strong smell and they did give me another one which was much better. Beds were pretty worn out, but the ..."

Reviewed on 25 Jun 2025

RumFish Beach at TradeWinds
See all 12,842 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Diamond Isle travel package cost?
Custom make your Diamond Isle travel package from an affordable £720. Pick from any combination of flights, hotels and rental cars to create the trip you've been dreaming about. Don't forget to add on one or two experiences!
If I'm not able to travel, can I cancel my Diamond Isle travel package?
If your travel plans in Diamond Isle have been upended, it's good to know that you can cancel your booking. If you booked within the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may charge a cancellation fee. For more information, check our Customer Service Portal.
How do I get a cheap travel package to Diamond Isle?
One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities --- we've got it all. Select the combination that best fits you and see your savings grow. We know a package deal 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 getaway.
Does Expedia offer Book Now, Pay Later Diamond Isle holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a dream getaway without draining your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds right for you, Klarna can help. Paying in easy monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: Clicking the "book now" button is easier with this plan. Put down a small deposit on your holiday and then get on your way.

Where should I stay in Diamond Isle?
A visit to Diamond Isle isn't complete until you've seen Clearwater Marine Aquarium and Sand Key Park. Reserve a room as close as possible and easily access these famous tourist attractions.
What are the top hotels in Diamond Isle?
Get your trip off to an excellent start by locking in a room at Wyndham Grand Clearwater Beach. It's one of most sought-after properties in Diamond Isle. Another welcoming option is Edge Hotel Clearwater Beach.
How far in advance should I book my Diamond Isle holiday?
It all depends on the airline, but it's usually possible to compare international airfares on Expedia up to 12 months in advance. While it's generally recommended to book ahead of time, lucky customers occasionally find a cheaper flight just weeks prior to their intended journey.
What does an Expedia Diamond Isle travel package include?
Much of that is up to you. You can select from a variety of Diamond Isle bundles, such as a rental car, hotel and flight. You can also book a hotel with a flight, or a rental car and a flight. Once you've made your booking, you can add on the fun stuff like activities and experiences. Whatever your Diamond Isle trip looks like, get set to save!
What should I know before booking a Diamond Isle travel package?
A travel package can be easier on the bank balance than separately booking all you need for your getaway. For example, combine your hotels, flights and rental cars and score big savings. Whatever sort of holiday you're planning, there's bound to be a package that's right for you.
Can I choose my airline with a Diamond Isle Expedia travel package?
Yes --- that's the beauty of an Expedia package. You can mix and match your flights, hotels and more. We have access to more than 550 airline partners worldwide, so you have lots of choice when creating your Diamond Isle trip.

Popular places to visit

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4/5(33 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 visit its lively bars.

John's Pass Village & Boardwalk
Tropicana Field

Tropicana Field

4.5/5(9 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
Fort De Soto Park featuring a beach

Fort De Soto Park

4.5/5(25 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

£24
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

£27
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

£92
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. Flight-inclusive packages are ATOL protected.