Island Estate Vacations from $475
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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.
Mar Bay Motel &Suites
Save 100% on your flight
Price was $765, price is now $475 per person
$475
per person
Aug 11 - Aug 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (80 reviews)
The room was a little noisy from the air conditioner and outside noise. The shower was way to high.
Reviewed on Jun 19, 2026
CW Hotel
Save 100% on your flight
Price was $1,869, price is now $1,012 per person
$1,012
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
We had such a great stay at the CW Resort in Clearwater! The pool area was beautiful and relaxing, the views were amazing, and the entire property was very clean and well maintained. It was the perfect place to unwind and enjoy a Florida getaway. We would definitely stay here again!
Reviewed on Jul 8, 2026
The Avalon Club
Save 100% on your flight
Price was $1,515, price is now $961 per person
$961
per person
Sep 24 - Sep 30
found 11 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (564 reviews)
The property was not what I was expecting. It was breathtaking. Stellar views of the water. The balcony was huge and my entire party was able to sit out and have morning coffee/tea. Our family will be back for future visits.
Reviewed on Jul 10, 2026
Cedar Cove Resort and Cottages
Save 100% on your flight
Price was $1,333, price is now $851 per person
$851
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (543 reviews)
Being able to stay on the beach well after dark was a plus. Plenty of lounge chairs and a bench swing. Loved it. Also loved the rocking chairs on our porch.
Pull out bed was surprisingly comfortable. Just wish there were more coffee pods - that’s the only recommendation I would make!
Reviewed on Jul 10, 2026
Wyndham Grand Clearwater Beach
Save 100% on your flight
Price was $1,625, price is now $1,049 per person
$1,049
per person
Sep 24 - Sep 30
found 11 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (3,447 reviews)
The resort was very nice, but it wasn’t always easy to grab towels and I wish the staff would ask for the passports for the discount to be used. We ended up forgetting to use it. Otherwise, the staff were all very nice and everything was clean.
Reviewed on Jul 12, 2026
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
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.
Island Estate Hotel Deals
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$252 nightly
The price is $285 total per night from Aug 2 to Aug 3
$285 total
Aug 2 - Aug 3
Total with taxes and fees
9.4/10 Exceptional! (3,531 reviews)
"The resort was very nice, but it wasn’t always easy to grab towels and I wish the staff would ask for the passports for the discount to be used. We ended up forgetting to use it. Otherwise, the staff were all very nice and everything was clean."
Reviewed on Jul 12, 2026
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $217 total per night from Aug 12 to Aug 13
$217 total
Aug 12 - Aug 13
Total with taxes and fees
8.2/10 Very Good! (2,815 reviews)
"Everything is good."
Reviewed on Jul 12, 2026
Hyatt Regency Clearwater Beach Resort and Suites
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $254 total per night from Aug 9 to Aug 10
$254 total
Aug 9 - Aug 10
Total with taxes and fees
9.2/10 Wonderful! (2,205 reviews)
"Good spot"
Reviewed on Jul 12, 2026
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.
Things to do
Sunset Celebration Cruise on Tropics Boat Tours
$37
per adult
92% of travellers recommend
Starlite Infinity Evening Yacht Cruise Clearwater
$37
per adult
90% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
$28
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.