Island Estate Vacations from $337

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Your Island Estate Vacation

Discover the unique character of Island Estate with a tailor-made Island Estate vacation package. From its watersports to its nature, this neighborhood offers endless possibilities for relaxation and adventure. Can't wait to get out and see the sights during your trip to Island Estate? Don't miss nearby attractions such as Clearwater Marine Aquarium, Sand Key Park and Pier 60 Park. No matter your travel goals or the size of your budget, booking the ultimate Island Estate vacation is easy with Expedia.

The Latest Island Estate 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
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9/10 Wonderful! (4,008 reviews)
Staff was very responsive and proactive about solving problems.

Reviewed on Jul 9, 2025

Coral Reef Beach Resort

Coral Reef Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
8.8/10 Excellent! (251 reviews)
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9.6/10 Exceptional! (499 reviews)
Perfect stay. Fresh and new.

Reviewed on Jul 9, 2025

Barsala At The Wayland Condos

Barsala At The Wayland Condos

4 out of 5
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
7.8/10 Good! (9 reviews)
My little getaway was amazing!!! The studio was beautiful, had everything we needed I wasn't expecting a full kitchen with baking utensils as well. We had a blast the view was incredible. I loved the outside setup near the pool as well. Will definitely be booking another getaway real soon!!

Reviewed on Jun 10, 2025

Siesta Key Palms Resort

Siesta Key Palms Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9.2/10 Wonderful! (1,000 reviews)
The property had a Key West vibe with hammocks, 2 pools, private porches, etc.

Reviewed on Jul 8, 2025

Where to stay in Island Estate

Find the best Island Estate areas and neighborhoods for the activities you enjoy most. Learn more about Island Estate
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

Island Estate 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
$238 nightly
The price is $269 total per night from Jul 16 to Jul 17
$269 total
Jul 16 - Jul 17
Total includes taxes and fees
8/10 Very Good! (1,997 reviews)
"The hotel was really nice!"

Reviewed on Jul 8, 2025

Hilton Clearwater Beach Resort & Spa
Wyndham Grand Clearwater Beach
Wyndham Grand Clearwater Beach
4 out of 5
100 Coronado Drive, Clearwater Beach, FL
$290 nightly
The price is $328 total per night from Aug 3 to Aug 4
$328 total
Aug 3 - Aug 4
Total includes taxes and fees
9.4/10 Exceptional! (2,352 reviews)
"Great stay!! Straight from the start til we had to leave. The cleanliness, atmosphere and layout was top notch! Dining options were excellent. We didn't get everyone's name but special shoutouts to Audra at the front desk, Marty(my boy) at the luggage desk, Nathan at Docks and John at Ocean Hai. ..."

Reviewed on Jul 6, 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
$151 nightly
The price is $172 total per night from Aug 3 to Aug 4
$172 total
Aug 3 - Aug 4
Total includes taxes and 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 13,394 properties in Island Estate
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 Island Estate

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 check out its lively bars.

John's Pass Village & Boardwalk
Tropicana Field

Tropicana Field

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
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

35 inch Snook we caught in 1 foot of water behind Clearwater Beach

Fishing Adventure in Clearwater

$600
per traveler
Fishing Adventure in Clearwater
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
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.