Bay Island Vacation Packages 2026 from $842

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.

Captiva Beach Resort

South Village

Save 100% on your flight

$842

per person

Dec 2 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,324 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,553

per person

Dec 27 - Jan 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,282 reviews)

Nice hotel

Reviewed on Oct 25, 2026

Stylish Treasure Island Escape

Sunshine Beach

$4,357

per person

Dec 4 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

No reviews

La Tortuga Historic Downtown Pass A Grille

Pass-a-Grille

$1,043

per person

Jan 13 - Jan 19

found 12 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (36 reviews)

Such a beautiful place!!! My only recommendation is they need to lock the gates at the pool! We left at 3:30 am and there were 3 people swimming in the pool… they took off running away when they saw us, so definitely not guests!!! The property is so beautiful and well cared for that I’d hate to see someone destroy something!

Reviewed on Oct 18, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,160

per person

Jan 15 - Jan 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (604 reviews)

Awesome resort, highly recommend if visiting AMI. Great location and can use free island trolley to go anywhere you want.

Reviewed on Oct 24, 2026

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 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.

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.

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

$70 nightly

$79 total

Oct 28 - Oct 29

Total with taxes and fees

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Fully refundableReserve now, pay when you stay

$163 nightly

$184 total

Nov 25 - Nov 26

Total with taxes and fees

9.4/10 Exceptional! (6,009 reviews)

""The receptionist's office was very customer-service-oriented and helpful with our needs. They communicated quickly via text and phone. The cleaning ladies were exceptional with their service and flexibility. This place is definitely 5-star in service and cleanliness, and the location was half a ..."

Reviewed on Oct 24, 2026

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Fully refundableReserve now, pay when you stay

$171 nightly

$194 total

Nov 4 - Nov 5

Total with taxes and fees

9.4/10 Exceptional! (2,635 reviews)

"Jennifer was very friendly and helpful when we checked in."

Reviewed on Oct 24, 2026

See all 14,765 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.