Island Estate Vacations from $521
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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.
voco Sarasota by IHG
Central Sarasota
Price was $804, price is now $521 per person
$521
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,012 reviews)
We enjoyed our stay at vocoSarasota.. The best part was the amazing and very accommodating staff especially the Shuttle drivers Rich, Barry and Cody. they were terrific.
Rooms were very nice. I just wished they had better outdoor accomodations especially the pool area.The daily breakfast was good even when the chef had to be the Manager on duty. Just a few hiccups with that. overall it was a delightful stay and the location was perfect!!!!
Reviewed on Mar 17, 2026
Mar Bay Motel &Suites
Save 100% on your flight
Price was $1,025, price is now $673 per person
$673
per person
Apr 26 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (68 reviews)
The property was perfect for pets. Big space to walk and off the main road.
Reviewed on Mar 23, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,191, price is now $829 per person
$829
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (846 reviews)
Beautiful hotel. Very clean, comfortable.
Had a great time.
The condos have everything you would need.
Reviewed on Mar 24, 2026
The Fold Hotels Indian Shores
Price was $784, price is now $563 per person
$563
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (955 reviews)
Stayed for three nights with my kids while visiting family in the area so we didn’t make full use of the property but it was fantastic for our needs! The areas were all well kept, our room was spacious and clean. Kids loved the pool/hot tub
Reviewed on Mar 23, 2026
The Barrymore Hotel Tampa Riverwalk
Downtown Tampa
Save 100% on your flight
Price was $1,152, price is now $827 per person
$827
per person
Apr 30 - May 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (2,526 reviews)
Check-in was easy and quick, same as checkout. Convenient shuttle to the docks, although it depends on how many people are ahead of you. Room is clean and quiet, nicely laid out for relaxing and watching TV.
Reviewed on Mar 22, 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
$282 nightly
The price is $319 total per night from Apr 12 to Apr 13
$319 total
Apr 12 - Apr 13
Total with taxes and fees
8.2/10 Very Good! (1,715 reviews)
Clean rooms, very nice staff, great dining options
Reviewed on Mar 24, 2026
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$391 nightly
The price is $442 total per night from Apr 16 to Apr 17
$442 total
Apr 16 - Apr 17
Total with taxes and fees
9.4/10 Exceptional! (3,074 reviews)
Great location and beautiful hotel the only thing is that the bartenders as well as the restaurant servers are “in no hurry” it takes some time to get served. If you don’t get your chair around the pool by 9am you can’t get one, ppl put their towels on them and walk away for breakfast. Also the hotel ...
Reviewed on Mar 23, 2026
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$324 nightly
The price is $366 total per night from Mar 25 to Mar 26
$366 total
Mar 25 - Mar 26
Total with taxes and fees
8.2/10 Very Good! (2,516 reviews)
Staff was great, location great, great view, the body scrub in the spa was so nice, toilet had to be flushed twice, low pressure I guess. The hotel is old and in some area a little rough. When we opened the sliding glass door to the small balcony, the frame came loose and almost fell off. A nice ...
Reviewed on Mar 24, 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(1,653 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.
Clearwater Beach
4.5/5(47 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.
St. Petersburg - Clearwater Beaches
4.5/5(6 reviews)
Why not spend a lazy afternoon at St. Petersburg - Clearwater Beaches during your trip to St. Petersburg - Clearwater?
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.