Bay Island Vacation Packages 2026 from $693

Your Bay Island Vacation

Bay Island is calling! Whatever type of break you're planning, you can experience and see more of this neighborhood with a Bay Island vacation package. Kick off your trip to Bay Island with a visit to nearby attractions such as Siesta Key Beach, St. Armands Circle and Mote Marine Laboratory & Aquarium. Don't just imagine it — make it happen! Reserve your ultimate Bay Island vacation with Expedia and travel your way.

The Latest Bay Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$693

per person

Oct 20 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,000 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$730

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,173 reviews)

Super clean, beautiful unit! The staff was absolutely amazing and courteous at every turn. We found our home when we are in the area.

Reviewed on Sep 1, 2026

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$816

per person

Oct 20 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,160 reviews)

This hotel has a great location. The staff is so nice they care you and go through all the details that makes you feel like home. The only thing was the breakfast that we found the bread wasn't fresh, the eggs tasted like boxed frozen food . The service was nice but too slow and meals were cold. I would recommend this hotel but please pay attention to the breakfast service! and thr service was too slow

Reviewed on Aug 31, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,548

per person

Oct 2 - Oct 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (584 reviews)

Wyndham Grand Clearwater Beach

Save 100% on your flight

$1,354

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,767 reviews)

Where to stay in Bay Island

Find the best Bay Island areas and neighborhoods for the activities you enjoy most. Learn more about Bay Island

A vibrant building with a purple facade, a sign reading "Siesta," and a staircase leading to the entrance.

Siesta Key Village

1 out of top 10 points of interest in this area

Tropical colored buildings, lots of sandy beaches and a compact shopping area make this village a good choice to visit and stay. Enjoy an on-going social life too.

A large, beige colonial-style building with columns, surrounded by palm trees and dense vegetation.

South Village

1 out of top 10 points of interest in this area

While visiting South Village, you might make a stop by sights like Safe Harbor Siesta Key and Crescent Beach.

Aloha Kai

While Aloha Kai isn't home to many top sights, Siesta Key Beach and Crescent Beach are some notable places to visit nearby.

Bailey Hall

When in Bailey Hall, you can plan a visit to Siesta Key Beach and Lido Beach, some noteworthy sights in the nearby area.

Point of Rocks

While there might not be top attractions in Point of Rocks, you can explore the larger area and discover places like Siesta Key Beach and Point of Rocks.

Bay Island Hotel Deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Fully refundableReserve now, pay when you stay

$62 nightly

$71 total

Sep 8 - Sep 9

Total with taxes and fees

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Fully refundableReserve now, pay when you stay

$168 nightly

$190 total

Sep 11 - Sep 12

Total with taxes and fees

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

$141 nightly

$160 total

Sep 3 - Sep 4

Total with taxes and fees

9.4/10 Exceptional! (5,826 reviews)

"everything we needed was walking distance from our room. Very convenient"

Reviewed on Sep 2, 2026

See all 14,317 properties in Bay Island

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.