Diamond Isle Holidays from £1,073

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to £195 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Packages with flights are ATOL protected

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.
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
per person
20 Jul - 27 Jul
found 17 hours ago
Return flight included
London (LON) to Tampa (TPA)
8.4/10 Very Good! (1,034 reviews)
The Beach a long way from the resort. There was no restaurant on the property but there were many in walking distance. Overall a good experience.

Reviewed on 5 Jun 2024

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
20 Jul - 27 Jul
found 17 hours ago
Return flight included
London (LON) to Tampa (TPA)
8.8/10 Excellent! (1,000 reviews)
Lively motel with great location and access to the beach. Friendly staff. Kitchenette is great convenience. Would stay again.

Reviewed on 2 Jun 2024

TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
per person
20 Jul - 27 Jul
found 17 hours ago
Return flight included
London (LON) to Tampa (TPA)
7.6/10 Good! (1,010 reviews)
The property is perfect for a family. The kids have a lot of fun with so many outdoor activities. The rooms need some updates. Overall, it is an ideal hotel if you want to have fun with your family, friends, and pets.

Reviewed on 3 Jun 2024

FUSION Resort Two Bedroom Suites

FUSION Resort Two Bedroom Suites

3.5 out of 5
per person
20 Jul - 27 Jul
found 17 hours ago
Return flight included
London (LON) to Tampa (TPA)
9.2/10 Wonderful! (944 reviews)
They always go above and beyond. We had a wonderful anniversary celebration here. Excellent customer service and a breathtaking view.

Reviewed on 3 Jun 2024

RumFish Beach Resort by TradeWinds

RumFish Beach Resort by TradeWinds

4 out of 5
per person
20 Jul - 27 Jul
found 17 hours ago
Return flight included
London (LON) to Tampa (TPA)
8.2/10 Very Good! (1,004 reviews)
I liked how friendly and helpful the staff is. The atmosphere is upbeat. It is clear the staffs' goal is to ensure the guests have a good time. The pool and outside of the property were exceptionally clean and cared for. At first glance, the room looked great, but looking closely you can see the bathroom is very worn and the corners of the floor need attention. My one complaint would be that nothing opens until 7 am. I am a very early riser and had to leave the property for coffee everyday. You do provide coffee and voffee makers, but i didn't have enough cream.

Reviewed on 5 Jun 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
Default Image

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

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 £102 per night from 1 Jul to 2 Jul
£102
per night
1 Jul - 2 Jul
8.6/10 Excellent! (1,027 reviews)
"Parking was great. Hotel was clean and well stocked"

Reviewed on 3 Jun 2024

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
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 £213 per night from 10 Jun to 11 Jun
£213
per night
10 Jun - 11 Jun
8.2/10 Very Good! (1,020 reviews)
"Wonderful"

Reviewed on 2 Jun 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 £173 per night from 27 Jun to 28 Jun
£173
per night
27 Jun - 28 Jun
7.2/10 Good! (2,262 reviews)
"Good atmosphere"

Reviewed on 4 Jun 2024

Sirata Beach Resort
See all 13,737 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 £1,073. 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

Image for John's Pass Village & Boardwalk

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 seaside in this family-friendly area or visit its top-notch restaurants.

John's Pass Village & Boardwalk
Image for Tropicana Field

Tropicana Field

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

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

£25
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

£28
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

£47
Per adult
100% of travellers recommend
Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar
See all activities in St. Petersburg - Clearwater

More trip options

* 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.