Island Estate Vacations from $757
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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.
The Sarasota Modern, a Tribute Portfolio Hotel
Central Sarasota
Save 100% on your flight
Price was $2,729, price is now $1,545 per person
$1,545
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (532 reviews)
Staff were really friendly from front desk to bartenders to valet. Food was excellent and pool was nice with a fun vibe. Parts of hotel are dated and parts are newly renovated. It’s in a great location. I would return.
Reviewed on Mar 9, 2026
Kompose Boutique Hotel
Save 100% on your flight
Price was $1,444, price is now $872 per person
$872
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (5,088 reviews)
Love the rooms. Comfy bed! Only disappointment for my husband was no coffee or coffee maker in room.
Reviewed on Mar 13, 2026
FUSION Resort Waterfront Suites
Save 100% on your flight
Price was $1,933, price is now $1,203 per person
$1,203
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,135 reviews)
The pool was the highlight of the stay...it was warm ..hot tub was great and deck area was great...only downside seemed to always out or low on towels....All staff were very friendly. Air conditioning was freat since it was 80 to 85 degrees all week...
Reviewed on Mar 12, 2026
Legoland Florida Hotel
Save 100% on your flight
Price was $1,194, price is now $762 per person
$762
per person
May 14 - May 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
9/10 Wonderful! (81 reviews)
We stayed here for the convenience of location to Legoland. Our room was the Adventure room. It was at the very end of the hallway and looked like it hadn't been used in awhile. The shelves were dusty and the bathtub even had dust in it. The room was pretty dark. The bed was relatively comfortable. It is an older hotel that could use a refresh. The disco elevator was fun for the kids. Breakfast was good but the floor around the tables was very dirty. We left an item behind and were very pleased when it was found and returned to us (for a hefty price) but we were very happy to get it back. Very difficult to contact this property by phone. Communication online or via text is strongly encouraged/preferred by the property.
Reviewed on Mar 9, 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
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 12 to Apr 13
$435 total
Apr 12 - Apr 13
Total with taxes and fees
9.4/10 Exceptional! (3,063 reviews)
Great hotel and location on the beach
Reviewed on Mar 13, 2026
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! (1,674 reviews)
My beach view was perfect, the staff was wonderful, the amenities were beyond...always something to do or nothing at all...your choice. The trip could not have been more relaxing.
Reviewed on Mar 13, 2026
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$315 nightly
The price is $356 total per night from Mar 25 to Mar 26
$356 total
Mar 25 - Mar 26
Total with taxes and fees
8.2/10 Very Good! (2,490 reviews)
You pay a resort fee and still have to pay valet every day your there and rent beach chairs and umbrellas for $96 a day not sure what the resort fee was for. Very friendly and clean but very expensive.
Reviewed on Mar 13, 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
4.5/5(1,625 reviews)
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
5/5(5 reviews)
Nothing says vacation like spending a carefree day at St. Petersburg - Clearwater Beaches, a popular beach in St. Petersburg - Clearwater.
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.
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.