Island Estate Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Island Estate

Price found within the past 48 hours. Click for updated prices.
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Price was CA $1,822, price is now CA $1,282 per person
CA $1,282
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (2,636 reviews)
very good location, well kept public areas and nice bar and pool

Reviewed on Jun 21, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,698, price is now CA $1,601 per person
CA $1,601
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews
The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,930, price is now CA $1,948 per person
CA $1,948
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (552 reviews)
The staff was very kind and accommodating. We will definitely look to book again.

Reviewed on Jun 19, 2026

The Marker

The Marker

2 out of 5
Price was CA $3,512, price is now CA $2,392 per person
CA $2,392
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
6/10 (3 reviews)
There was no staff due to it being brand new! The owner Jeff was great and very polite and went out of his way to make us feel welcome and valued! It was very quiet and comfortable for my family. Only about a two block walk to the beach but being in the bay was beautiful to wake up to!

Reviewed on Apr 12, 2026

Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3 out of 5
Price was CA $2,079, price is now CA $1,465 per person
CA $1,465
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (453 reviews)
Great little place, very small rooms but very clean and nice. Having to check in at a different location was a bit odd but overall a good place.

Reviewed on Jun 15, 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
Pass-a-Grille

Pass-a-Grille

1 out of top 10 points of interest in this area

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.

Find hotels in Pass-a-Grille

Island Estate Hotel Deals

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $365 per night from Jul 16 to Jul 17
CA $365
CA $469 total
Jul 16 - Jul 17
includes taxes & fees
9.4/10 Exceptional! (3,395 reviews)
"Great location close to anything you need on a vacation. Staff was friendly and helpful."

Reviewed on Jun 21, 2026

Wyndham Grand Clearwater Beach
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $296 per night from Jun 28 to Jun 29
CA $296
CA $390 total
Jun 28 - Jun 29
includes taxes & fees
8.2/10 Very Good! (2,706 reviews)
"We had a very nice stay. However the restaurants leave much to be desired. Lots of tasteless foods. That being said it would be a wonderful service if they would serve the people renting the cabanas at the beach for $175 a day to order food to be delivered there."

Reviewed on Jun 21, 2026

Hilton Clearwater Beach Resort & Spa
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $228 per night from Jul 1 to Jul 2
CA $228
CA $346 total
Jul 1 - Jul 2
includes taxes & fees
8.2/10 Very Good! (2,049 reviews)
"Amazing hotel, location, and amenities. Considering coming back!"

Reviewed on Jun 21, 2026

RumFish Beach at TradeWinds
See all 14,308 properties in Island Estate
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,282. 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.

Discover the most popular places to visit in Island Estate

A coastal cityscape with a prominent waterfront, a bridge, and a distinctive building with a red facade.

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 lively bars.

John's Pass Village & Boardwalk
Aerial sunset view of Clearwater beach and Sand key in Western Florida on the Mexican Gulf coast with vacation homes, hotels and bridges connecting

Clearwater Beach

Nothing says vacation like spending a carefree day at Clearwater Beach, a popular beach in Clearwater Beach. Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach
Fort De Soto Park

Fort De Soto Park

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $51
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $51
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

CA $55
per adult
90% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.