Island Estate Vacations from $414
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
Mar Bay Motel &Suites
Reviewed on Feb 26, 2026
FUSION Resort Waterfront Suites
Reviewed on Mar 15, 2026
Ocean Club Treasure Island Hotel
Reviewed on Mar 15, 2026
SkyBeach Resort
Reviewed on Mar 14, 2026
Pelican Pointe Clearwater Beach Hotel
Reviewed on Mar 14, 2026
Where to stay in Island Estate
Downtown St. Petersburg
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
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
RumFish Beach at TradeWinds
Staff is friendly, very family oriented, my children enjoyed it, currently the property is being renovated, but it wasn’t in our way or hindered our stay at the time. Love the access to the beach, drinks were good but a bit on the higher price,We did bring a cooler, ice was available and no issues ...
Reviewed on Mar 15, 2026
Hilton Clearwater Beach Resort & Spa
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
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
StarLite Majesty Evening Yacht Cruise Clearwater
