Island Estate Vacations from ￥258,889

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The Latest Island Estate Vacation Packages

Price found within the past 48 hours. Click for updated prices.
EVEN Hotel Sarasota-Lakewood Ranch by IHG

EVEN Hotel Sarasota-Lakewood Ranch by IHG

3.5 out of 5
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
8.4/10 Very Good! (994 reviews)
I love this hotel! Comfortable and clean! I really recommend!

Reviewed on Jul 8, 2025

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
8.6/10 Excellent! (2,137 reviews)
Espectacular el lugar lo único que no nos gustó que la piscina la cierran temprano en tiempo de verano deberían cerrarla a las 10 pm

Reviewed on Jul 6, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
9.2/10 Wonderful! (1,008 reviews)
The hotel staff (Maria front desk and Rich shuttle driver) set the standard for how guest should be treated. Maria greeted us with a smile each time at the desk, provided us with essentials if needed, and pertinent information about the area. We rented bicycles from the hotel and got stuck in a storm. Rich came immediately to pick myself and my daughter up. He loaded the bicycles and instructed us to stay under protection until he did so. He brought us towels to dry off in the van and instructed us to take hot showers when returned to avoid getting sick! True genuine concern was shown to me and my daughter. The other transport guy was really nice as well but I forget the name. The pool was rather small but that’s ok we spent most time at the beaches. The bicycle and beach chair rentals are an amazing perk in addition to the hotel shuttle (within 3 mile radius). Hotel is walkable to the Bayfront park and lido beach is only a 10 min drive in which you can take the shuttle. Also visited siesta key beach but had to uber there. The hotel was clean and housekeeping popped in promptly to tidy up and replenish essentials. Will recommend this hotel thanks so much Voco staff.

Reviewed on Jul 7, 2025

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
9/10 Wonderful! (1,013 reviews)
Had a great time at this property. Staff was nice and accommodating. Property was very clean and pretty,

Reviewed on Jul 7, 2025

Carlisle Inn

Carlisle Inn

3.5 out of 5
Pinecraft
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Tampa (TPA)
10/10 Exceptional! (1,868 reviews)
We had such an amazing experience here. We will definitely be back again.

Reviewed on Jul 6, 2025

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

5/5(26 area reviews)

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

Hilton Clearwater Beach Resort & Spa
Hilton Clearwater Beach Resort & Spa
4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
The price is ￥28,025 per night from Jul 14 to Jul 15
￥28,025
￥37,437 total
Jul 14 - Jul 15
includes taxes & fees
8/10 Very Good! (1,979 reviews)
"Had a great stay. Easy to get around to restaurants and stores in foot."

Reviewed on Jul 5, 2025

Hilton Clearwater Beach Resort & Spa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4 out of 5
4860 West Kennedy Boulevard, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is ￥22,058 per night from Aug 3 to Aug 4
￥22,058
￥25,036 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (1,638 reviews)
"Very beautiful"

Reviewed on Jul 5, 2025

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
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 ￥37,231 per night from Aug 3 to Aug 4
￥37,231
￥47,840 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (2,352 reviews)
"Great stay!! Straight from the start til we had to leave. The cleanliness, atmosphere and layout was top notch! Dining options were excellent. We didn't get everyone's name but special shoutouts to Audra at the front desk, Marty(my boy) at the luggage desk, Nathan at Docks and John at Ocean Hai. ..."

Reviewed on Jul 6, 2025

Wyndham Grand Clearwater Beach
See all 13,394 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.

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 ￥258,889. 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

John's Pass Village & Boardwalk

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 lively bars.

John's Pass Village & Boardwalk
Tropicana Field

Tropicana Field

4.5/5(591 reviews)

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the lively bars while you're in the area.

Tropicana Field
Fort De Soto Park which includes a sandy beach

Fort De Soto Park

4.5/5(676 reviews)

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

35 inch Snook we caught in 1 foot of water behind Clearwater Beach

Fishing Adventure in Clearwater

￥86,790
per traveler
Fishing Adventure in Clearwater
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

￥4,636
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

￥5,352
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
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.