Island Estate Vacations from $414
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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
Price was $602, price is now $414 per person
$414
per person
May 29 - Jun 1
found 9 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
8.6/10 Excellent! (68 reviews)
Staff was very responsive although we did not meet in person. Very old but clean Florida Motel which is all we needed for the night and the price was good!
Reviewed on Feb 26, 2026
Pelican Pointe Clearwater Beach Hotel
Save 100% on your flight
Price was $1,301, price is now $893 per person
$893
per person
May 20 - May 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,010 reviews)
We had a partial view of the beach. Pool was heated and clean. Staff was lovely. Our bathtub needs to be reglazed (room 229).
Reviewed on Mar 14, 2026
Crystal Palms Beach Resort
Sunshine Beach
Save 100% on your flight
Price was $1,616, price is now $1,111 per person
$1,111
per person
May 20 - May 27
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (4 reviews)
There was construction going on all around us, and it was very loud when I was trying to take a nap. Aside from the sound, there was plastic and tape everywhere and furniture blocking the hallway. The elevators were slow as ever, and at one point I thought we were stick because the doors wouldn't open. But despite all this, the worst part was the mattress in each room.. both my boyfriend and I had very sore backs after night 1.. and he ended up sleeping on the couch for nights 2 and 3.. while I just suffered through it since there was nowhere else. All in all, it was not the best experience. But the balcony was huge and the view was nice.
Reviewed on Mar 15, 2026
Hotel Alba, Tapestry Collection by Hilton
Westshore
Price was $990, price is now $695 per person
$695
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (2,571 reviews)
Great hotel, convenient to the airport. Bed was great.
Reviewed on Mar 16, 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
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.
Island Estate Hotel Deals
RumFish Beach at TradeWinds
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
$309 nightly
The price is $349 total per night from Mar 22 to Mar 23
$349 total
Mar 22 - Mar 23
Total with taxes and fees
8.4/10 Very Good! (1,686 reviews)
If you have shellfish allergy they cannot accommodate you at any restaurant except the pizza during the day. For dinner they can. So just know hanging at the pool or beach you will need to go else where for food. Our toilet overflowed twice, the room with double bed is actually the size of a single ...
Reviewed on Mar 16, 2026
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$385 nightly
The price is $435 total per night from Apr 16 to Apr 17
$435 total
Apr 16 - Apr 17
Total with taxes and fees
9.4/10 Exceptional! (3,073 reviews)
We had a gulf-front room, so the view of the beach & ocean was great. Noise from the street and other events could be a bit however, the patio doors/windows were pretty solid so not a lot of noise got inside the room. Staff was great, helpful and friendly. Nice location. Pricey, for one, i don't ...
Reviewed on Mar 15, 2026
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$319 nightly
The price is $361 total per night from Mar 22 to Mar 23
$361 total
Mar 22 - Mar 23
Total with taxes and fees
8.2/10 Very Good! (2,496 reviews)
Hilton was beautiful! You couldn’t ask for a better location right on the beach and 2 pools. You could walk to shops, restaurants, the park and pier. Staff went above and beyond every day! We actually booked extra days because we loved it so much!
Reviewed on Mar 15, 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.
Discover the most popular places to visit in Island Estate
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 top-notch restaurants.
St. Petersburg - Clearwater Beaches
Nothing says vacation like spending a carefree day at St. Petersburg - Clearwater Beaches, a popular beach in St. Petersburg - Clearwater.
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.
Things to do
Sunset Celebration Cruise on Tropics Boat Tours
$37
per adult
92% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
$37
per adult
90% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
$37
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.