Bay Island Vacations from $316
Book a Hotel + Flight or Car together to unlock savings
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.
Barsala At Gateway Commons
Save 100% on your flight
per person
Sep 26 - Oct 3
found 14 hours ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
9/10 Wonderful! (32 reviews)
the property was very quiet and friendly. fast response from property manager. loved the amenities and the pool. nice workout place and bathrooms were very clean. the pool area had a kitchen and propane grills to cook in. loved it.
I felt uncomfortable leaving the keys in the apartment and the apartment was left unlocked. Recommendation would be nice to lock the apartment and leave the key in the place where we obtained it from.
Reviewed on Jun 15, 2025
Barsala At The Wayland Condos
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
7.8/10 Good! (9 reviews)
My little getaway was amazing!!! The studio was beautiful, had everything we needed I wasn't expecting a full kitchen with baking utensils as well. We had a blast the view was incredible. I loved the outside setup near the pool as well. Will definitely be booking another getaway real soon!!
Reviewed on Jun 10, 2025
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
Siesta Key Village
1 out of top 10 points of interest in this area
4.5/5(282 area reviews)
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.
Bay Island Hotel Deals
Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $89 total per night from Jul 13 to Jul 14
$89 total
Jul 13 - Jul 14
Total includes taxes and fees
9/10 Wonderful! (4,087 reviews)
"Excellent"
Reviewed on Jul 7, 2025
Tropical Beach Resorts
6717 Sara Sea Circle, Siesta Key, FL
$164 nightly
The price is $185 total per night from Jul 10 to Jul 11
$185 total
Jul 10 - Jul 11
Total includes taxes and fees
9.2/10 Wonderful! (4,753 reviews)
Stancy at Siesta Key
"Was good , attention from personal was good . The habitation is comfortable."
Reviewed on Jul 6, 2025
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West, Bradenton, FL
Fully refundableReserve now, pay when you stay
$197 nightly
The price is $223 total per night from Jul 16 to Jul 17
$223 total
Jul 16 - Jul 17
Total includes taxes and fees
9.4/10 Exceptional! (1,541 reviews)
"Hospitality is great! Everything is clean and tidy !love the scenic view in and around the hotel. Enjoyed the stay !"
Reviewed on Jul 6, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.