Bay Island Vacations from $344
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.
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $554, price is now $344 per person
$344
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
It was nice to have a gym available and it was always empty. Shower was my favorite park, really big and open, bed was super comfy. The elevators were outnof order though and the coffee machine in the room didnt work, but over all it was a pretty nice hotel. One of the nicest ive been too.
Reviewed on Oct 4, 2025
FUSION Resort Waterfront Suites
Save 100% on your flight
Price was $2,313, price is now $1,269 per person
$1,269
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,068 reviews)
Have stayed here a couple times now and would definitely go back. Love the vibes. Only thing that was a bummer is that my daughter and I love using the complimentary bikes to ride around town. However, the bikes are in pretty rough shape. If doable, I would consider maybe replacing the bikes.
Reviewed on Oct 7, 2025
Captiva Beach Resort
South Village
Save 100% on your flight
Price was $1,087, price is now $669 per person
$669
per person
Jan 2 - Jan 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9/10 Wonderful! (1,132 reviews)
I would give it 4.5⭐️ Everyone who works there was wonderful.y only issue was the room smelled like smoke.
Reviewed on Sep 25, 2025
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $748, price is now $466 per person
$466
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
Excellent room and facility . Clean and exactly like online pictures .
Reviewed on Oct 9, 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
$71 nightly
The price is $81 total per night from Oct 16 to Oct 17
$81 total
Oct 16 - Oct 17
Total with taxes and fees
9/10 Wonderful! (4,408 reviews)
"Excellent!"
Reviewed on Oct 5, 2025
Tropical Beach Resorts
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $166 total per night from Oct 13 to Oct 14
$166 total
Oct 13 - Oct 14
Total with taxes and fees
9.2/10 Wonderful! (5,015 reviews)
"My wife and I came here for our honeymoon and it was a wonderful experience! My wife didn’t want to leave. Everything was clean, housekeeping was excellent it was so much to do and so many free forms or transportation! EVERYONE was nice, and the beach clean and breath taking. I can’t wait to go ..."
Reviewed on Oct 6, 2025
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West, Bradenton, FL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $229 total per night from Oct 12 to Oct 13
$229 total
Oct 12 - Oct 13
Total with taxes and fees
9.4/10 Exceptional! (1,787 reviews)
"Check in great, graded was our 7th anniversary"
Reviewed on Oct 8, 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.
