Diamond Isle Vacations from $367

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Your Diamond Isle Vacation

Book a Diamond Isle vacation package and discover the rhythm and lifestyle of this captivating neighborhood. With all your travel plans worked out, the only thing you need to concentrate on here is living your best life. Not sure what to do during your trip to Diamond Isle? Nearby attractions such as Clearwater Marine Aquarium, Sand Key Park and Pier 60 Park are good places to begin. Expedia can help turn your ideal Diamond Isle vacation into reality, whatever your budget or travel plans.

The Latest Diamond Isle Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $708, price is now $367 per person
$367
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
18.4/10 Exceptional! (4,624 reviews)
Staff was great! Room clean! Food and drink was tasty 😊

Reviewed on Nov 21, 2025

Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Price was $1,157, price is now $558 per person
$558
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
16.4/10 Exceptional! (1,002 reviews)
Yes, the staff was very courteous and accommodating. The lobby was bright and clean. . The room was clean and roomie very comfortable. The pool was clean and the hot tub was so relaxing. Breakfast each morning was consistently delicious and even a beautiful presentation liked having the convenience of purchasing products right on the site.

Reviewed on Nov 20, 2025

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $798, price is now $428 per person
$428
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
17.2/10 Exceptional! (2,193 reviews)
Spotless room with fully stocked kitchen area! Friendly staff and clean pool! We had a great stay at Hibiscus suites and would stay again!

Reviewed on Nov 21, 2025

DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

4 out of 5
Save 100% on your flight
Price was $1,139, price is now $628 per person
$628
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
17.6/10 Exceptional! (1,501 reviews)
Friendly staff, clean rooms and easy parking. Close to the airport. Outdoor seating area with fire pit was nice!

Reviewed on Nov 18, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,711, price is now $989 per person
$989
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
18.8/10 Exceptional! (481 reviews)
Excellent staff. Very clean, spacious, great location

Reviewed on Nov 17, 2025

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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
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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)

You can do some window-shopping at John's Pass Village & Boardwalk during your stay in Madeira Beach. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

5/5(5 reviews)

Why not spend a lazy afternoon at St. Petersburg - Clearwater Beaches during your trip to St. Petersburg - Clearwater?

St. Petersburg - Clearwater Beaches
Clearwater Beach

Clearwater Beach

4.5/5(44 reviews)

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

Things to do

The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

$37
per adult
88% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$32
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

$35
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
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.