Bay Island Vacations from $240
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.
Compass Hotel by Margaritaville Anna Maria Sound
Save 100% on your flight
Price was $1,037, price is now $538 per person
$538
per person
Jan 27 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
18.8/10 Exceptional! (1,843 reviews)
It was awesome and the staff was great,the manager was awesome,I had an issue with my booking and he took care of me,stand up guy
Reviewed on Nov 23, 2025
Hilton Garden Inn Sarasota - Bradenton Airport
Save 100% on your flight
Price was $789, price is now $414 per person
$414
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
16.4/10 Exceptional! (1,002 reviews)
Staff was very friendly and happy to help. The room was clean. The front area was organized, and plenty of snack items were available to purchase.
Reviewed on Nov 24, 2025
Hibiscus Suites - Gateway to Siesta Key
Save 100% on your flight
Price was $1,468, price is now $771 per person
$771
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
17.2/10 Exceptional! (2,193 reviews)
Spotless room with fully stocked kitchen area! Friendly staff and clean pool! We had a great stay at Hibiscus suites and would stay again!
Reviewed on Nov 21, 2025
Crystal Palms Beach Resort
Sunshine Beach
Price was $1,774, price is now $936 per person
$936
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
17.6/10 Exceptional! (2,355 reviews)
Been here before. Love the view and location. Beautiful rooms, fully equipped with all you need for cooking. Looking forward to seeing you again soon.
Reviewed on Nov 23, 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
$73 nightly
The price is $82 total per night from Dec 1 to Dec 2
$82 total
Dec 1 - Dec 2
Total with taxes and fees
9/10 Wonderful! (4,675 reviews)
Great
Reviewed on Nov 23, 2025
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $140 total per night from Nov 30 to Dec 1
$140 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (5,110 reviews)
The staff was so helpful & friendly. The room was clean & the amenities were awesome.
Reviewed on Nov 23, 2025
Carlisle Inn
3727 Bahia Vista Sarasota FL
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $142 total per night from Nov 30 to Dec 1
$142 total
Nov 30 - Dec 1
Total with taxes and fees
9.8/10 Exceptional! (2,101 reviews)
Get find, hotel is very clean and the room is spacious. The complimentary cookies every evening was amazing.
Reviewed on Nov 22, 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.