Bay Island Vacation Packages

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Top Holiday Package Deals in Bay Island

Price found within the past 48 hours. Click for updated prices.
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
per person
Sep 26 - Sep 29
found 14 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Sarasota (SRQ)
9/10 Wonderful! (859 reviews)
It is difficult to get the bill at the end of your stay emailed to you, but the stay and property was really nice. The young waitress was absolutely amazing with impeccable customer service. Loved the atmosphere and the beds are really spacious and not like other hotels that claim they gave you a queen and it looks like a double. I just wished room service gave the room a proper cleaning while we were there at least once or twice for the 8 nights we stayed and not just straightening up the room.

Reviewed on Aug. 5, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Sarasota (SRQ)
9.8/10 Exceptional! (274 reviews)
Beachfront location is great!!

Reviewed on Jul. 22, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Oct 24 - Oct 27
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (557 reviews)
Everything was great. Beautiful view from our room. Surer clean. For sure will stay again.

Reviewed on Aug. 4, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
per person
Oct 24 - Oct 27
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,046 reviews)
Everything is great. Lacking food on the property and roof top bar doesn’t exist anymore

Reviewed on Aug. 1, 2025

Clearwater Suites

Clearwater Suites

2.5 out of 5
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.4/10 Very Good! (9 reviews)
Very conveniently located. Great room size and comfortable bed.

Reviewed on Aug. 5, 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
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Siesta Key Village

1 out of top 10 points of interest in this area
4.5/5(12 area reviews)

Travelers to Siesta Key Village praise its stunning beaches. If you've got some more time to explore, be sure to make a stop by Siesta Key Beach and Siesta Key Farmers Market.

Find hotels in Siesta Key Village

Bay Island Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is CA $73 per night from Aug 10 to Aug 11
CA $73
CA $98 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (4,220 reviews)
"Fabulous hotel! We really enjoyed our stay. The hotel decor is so individual. Great breakfast which was included as we booked through Expedia. We liked the hotel and Sarasota so much we booked an extra 2 nights."

Reviewed on Aug. 4, 2025

Kompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Sep 1 to Sep 2
CA $192
CA $247 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (4,831 reviews)
"The BEST place on the island. We’ve been coming here for 20 years and it just keeps getting better!!! The staff is so accommodating and will do anything for you. The new pool is absolutely amazing!!! We are sooo glad that they’ve been able to recover from the devastating hurricanes last year."

Reviewed on Aug. 5, 2025

Tropical Beach Resorts
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West, Bradenton, FL
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Aug 14 to Aug 15
CA $221
CA $283 total
Aug 14 - Aug 15
includes taxes & fees
9.4/10 Exceptional! (1,627 reviews)
"Wonderful."

Reviewed on Aug. 4, 2025

Compass Hotel by Margaritaville Anna Maria Sound
See all 13,175 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.
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Frequently asked questions

How much does a Bay Island vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Bay Island from just CA $523. And the more you bundle, the more money you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Bay Island?
Bundle your flights and hotels, throw in extras such as activities or a rental car, and save with a Bay Island vacation package. You won't just score impressive discounts on your trip — you'll have plenty of choice at your fingertips too. When you book with Expedia, you can select from more than 550 partner airlines and 1,000,000 properties around the world. Your next affordable adventure starts right here, right now!
Where should I stay in Bay Island?
If you love being where the action is, stay near Siesta Key Beach. Many vacationers book a hotel around this impressive tourist attraction.
What are the top hotels in Bay Island?
Get your vacation off to a good start by booking a stay at Baydream Bungalow | Pet Friendly Home W. It's one of most sought-after hotels in Bay Island. Another comfortable option is The Seagrape Villa - Luxury Accommodation In Paradise.
How far in advance should I book my Bay Island vacation?
To land rock-bottom prices, book as soon as you can. Air carriers typically advertise flight tickets, along with some of the lowest fares, around 12 months in advance. Hotels, experiences and car rental should also be booked well in advance to avoid disappointment. If you're in need of a last-minute getaway to Bay Island, there are always plenty of great deals on Expedia. Book your escape today!
What does an Expedia Bay Island travel package include?
Rental cars, hotels and flights, or any combination of them — it's your choice. Whether you're headed to Bay Island with the whole family or enjoying a solo break, there's a package to match every budget and style. Once you've made your booking, why not add on a few tours or activities?
What should I know before booking a Bay Island travel package?
Our prices are always low. However, you'll score even better deals if you book your flights, hotels and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a terrific range of choice.
Can I choose my airline with a Bay Island Expedia vacation package?
With a vacation package, you're the boss. Whether you're looking to fly to Bay Island in coach or business class, simply pick from the available airline options. Expedia has access to over 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Bay Island vacation package?
Whether it's your hotel, flight or rental car, you can cancel or change it. Locked in your Bay Island vacation package in the last 24 hours? You may be able to make changes at no cost. If it's been longer than that, you may be charged a fee by your airline, hotel or car rental company. For further information, visit our Customer Service Portal. We're here to help you every step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.