Diamond Isle Vacations from $372

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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.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $682, price is now $372 per person
$372
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,006 reviews)
Voco was an excellent choice for a night away from home. The service was top-notch, with a staff that was truly accommodating. Exceptional location with a shuttle that takes you where ever within 3 miles. I want to give a special shout-out to Rich and Tiffany, who went above and beyond to share their favorite local spots for dining and entertainment. Overall. I enjoyed my stay and highly recommend Voco!

Reviewed on Aug 28, 2025

Clearwater Suites

Clearwater Suites

2.5 out of 5
Save 100% on your flight
Price was $1,060, price is now $608 per person
$608
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (19 reviews)
Super convenient, clean, and right across the street from the beach. Staff was very friendly

Reviewed on Aug 25, 2025

GALAXY HOTEL

GALAXY HOTEL

3.5 out of 5
Downtown St. Petersburg
Save 100% on your flight
Price was $969, price is now $562 per person
$562
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (362 reviews)
Randy was really nice and helpful

Reviewed on Aug 29, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $813, price is now $484 per person
$484
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (609 reviews)
looked brand new, absolutely beautiful inside As soon as you open the door, you can see down the hallway of a view of the Gulf. You are truly renting a 2bedroom, 2bath condo with a full kitchen and full size washer and dryer...everything you would need!

Reviewed on Aug 29, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,301, price is now $800 per person
$800
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,592 reviews)
Everything was great.

Reviewed on Aug 29, 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
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

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
$221 nightly
The price is $250 total per night from Sep 7 to Sep 8
$250 total
Sep 7 - Sep 8
Total with taxes and fees
Hilton Clearwater Beach Resort & Spa
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $155 total per night from Sep 7 to Sep 8
$155 total
Sep 7 - Sep 8
Total with taxes and fees
8.6/10 Excellent! (2,103 reviews)
"Beautiful hotel… very helpful staff… great food and bar and pool area. Daughter goes to U Tampa and I will definitely be staying here again!"

Reviewed on Aug 27, 2025

Hotel Alba, Tapestry Collection by Hilton
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
$184 nightly
The price is $208 total per night from Sep 2 to Sep 3
$208 total
Sep 2 - Sep 3
Total with taxes and fees
RumFish Beach at TradeWinds
See all 12,943 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 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

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

John's Pass Village & Boardwalk
The sunset behind the lifeguard tower in combination with a bit of filtering made this image quite unique. #LifeAtExpedia

Clearwater Beach

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
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

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

St. Petersburg - Clearwater Beaches

Things to do

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$32
per adult
88% 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
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

$37
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
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.