Island Estate Vacation Packages 2026 from $462

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

$462

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,007 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$867

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,128 reviews)

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,441

per person

Oct 2 - Oct 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (568 reviews)

I loved it here, would come back! 5 out of 5 stars! We had everything we needed!

Reviewed on Aug 11, 2026

CW Hotel

Save 100% on your flight

$974

per person

Oct 15 - Oct 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (48 reviews)

Sueñe

Reviewed on Aug 11, 2026

The Westin Sarasota

Central Sarasota

$847

per person

Oct 17 - Oct 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,151 reviews)

Had a wonderful experience, convenient location

Reviewed on Aug 12, 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

A beach with people, a city skyline, and a distinctive pink building.

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.

A modern plaza with a large sculpture, palm trees, and a high-rise building in the background.

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.

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 St. Petersburg - Clearwater Beaches and Sand Key Park.

A beach with people walking along the shore, waves crashing onto the sand, and a city skyline in the background.

Sunset Beach

Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like St. Petersburg - Clearwater Beaches and Sunset Beach.

A sunset over the ocean with a person paddleboarding and a floating structure.

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

$247 nightly

$279 total

Aug 24 - Aug 25

Total with taxes and fees

The Westin Tampa Bay

7627 W Courtney Campbell Cswy Tampa FL

Fully refundableReserve now, pay when you stay

$143 nightly

$163 total

Aug 31 - Sep 1

Total with taxes and fees

8.6/10 Excellent! (1,498 reviews)

"Great stay"

Reviewed on Aug 12, 2026

Hilton Clearwater Beach Resort & Spa

400 Mandalay Ave Clearwater Beach FL

$198 nightly

$224 total

Aug 19 - Aug 20

Total with taxes and fees

See all 14,470 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.