Island Estate Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Top Holiday Package Deals in Island Estate
Price found within the past 48 hours. Click for updated prices.
CW Resort
CA $1,639
per person
Jan 8 - Jan 15
found 8 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
9.4/10 Exceptional! (204 reviews)
Excellent stay,beautiful room for my annual girls trip of seven. Plenty of room,comfortable beds and close to beach,restaurants and bars.Only wish was that the pool had a more upbeat vibe with music and we were able to have food and drinks while relaxing at the pool..
Reviewed on Oct 18, 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.
Pass-a-Grille
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.
Sand Key
1 out of top 10 points of interest in this area
While visiting Sand Key, you might make a stop by sights like Belleair Beach and Sand Key Park.
Sunset Beach
Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like Sunset Beach and St. Petersburg - Clearwater Beaches.
Sunshine Beach
If you're spending some time in Sunshine Beach, St. Petersburg - Clearwater Beaches and St. Petersburg Municipal Beach at Treasure Island are top sights worth seeing.
Island Estate Hotel Deals
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $290
CA $383 total
Oct 28 - Oct 29
includes taxes & fees
9.4/10 Exceptional! (3,994 reviews)
"Great experience. We will be back to enjoy the hotel and Clear Water Beach."
Reviewed on Oct 19, 2026
Hyatt Regency Clearwater Beach Resort and Suites
301 S Gulfview Blvd Clearwater Beach FL
Fully refundableReserve now, pay when you stay
CA $336
CA $436 total
Oct 20 - Oct 21
includes taxes & fees
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
CA $219
CA $249 total
Oct 25 - Oct 26
includes taxes & fees
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.
Frequently asked questions
How much does an Island Estate vacation package cost?
Go from looking to booking with our Island Estate vacation packages, which start from a low CA $1,121. Choose the flights and hotels that suit your travel plans. Then, add on some sightseeing tours to round off your unique adventure.
How do I get a cheap travel package to Island Estate?
Combine your bookings with Expedia to save on your next getaway. With more than 550 airlines and 1,000,000 properties worldwide, your Island Estate vacation package can be customized exactly to suit your travel style. With all those extra dollars, why not throw in some awesome tours and activities? It's an easy way to unlock even more bargains. Your dream vacation in Island Estate is much closer than you thought!
Where should I stay in Island Estate?
A journey to Island Estate isn't complete without stopping by Clearwater Marine Aquarium and Sand Key Park. Book somewhere right nearby so you can easily access these terrific tourist attractions.
What are the top hotels in Island Estate?
Get your vacation off to a good start by reserving a room at 818 Harbor Island - 4 Bedroom Condo. It's one of most popular properties in Island Estate. Another welcoming option is Starboard Clipper Cove #605 - 2 Bedroom Apts.
How far in advance should I book my Island Estate vacation?
Travelers are generally able to look up international fares on Expedia within 12 months of departure. Booking last minute? With a stroke of luck, it's still possible to purchase an affordable ticket just weeks before your flight.
What does an Expedia Island Estate travel package include?
Flights, car rentals and hotels — we bring you the very best bargains. All you have to do is figure out your favorite combination. After you've made your booking, you can add on the fun stuff like activities and sightseeing tours. Our travel packages make it easy to create an unforgettable Island Estate escape.
What should I know before booking an Island Estate travel package?
Our prices are always low. However, you'll enjoy even more bargains if you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and a great range of choice.
Can I choose my airline with an Island Estate Expedia vacation package?
Yes, and with over 550 airlines to pick from around the world, you've got lots of choice. Take a look at the available options and find out which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Island Estate vacation package?
We totally understand — life sometimes gets in the way of your plans. If you've booked an Island Estate vacation package and have to cancel or change it, we're here to help. We recommend looking up our Customer Service Portal first for information. But generally speaking, if you've taken out your package within 24 hours, you may be able to change your itinerary at no cost. If it's more than 24 hours, your airline, hotel or car rental company may charge a fee.
Things to do
Starlite Infinity Evening Yacht Cruise Clearwater
CA $51
per adult
90% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
CA $39
per adult
94% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
CA $52
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.