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.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

Sunshine Beach
CA $1,036
per person
Nov 14 - Nov 21
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,173 reviews)
Firt time I'm treasure island first time at ocean club and I will definitely come back sooner than later. The only bad thin was today check out day for some reason housekeeping team n

Reviewed on Sep 1, 2026

CW Resort

CW Resort

CA $1,229
per person
Nov 14 - Nov 21
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (117 reviews)
Amazing brand new hotel, spacious rooms , breathtaking views , hotel is spotless. Very convenient location, close to every attraction , less than 5 minutes walk to the beach .

Reviewed on Sep 1, 2026

The Avalon Club

The Avalon Club

CA $1,346
per person
Nov 14 - Nov 21
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (590 reviews)
2/5 stars — Avoid: False advertising, poor conditions, and dishonest billing We booked 5 nights at the Avalon but left after 3 due to a string of issues. The "beachfront" view advertised on their website was misleading — in reality, our room overlooked a public parking lot, with the actual beach a few hundred feet beyond that. Amenities weren't much better: the towels and pool/beach chairs were worn out and old, despite an extra $40/day charge to use them. The shower grout was visibly moldy and the sofa looked like they got it off of a curb. After complaining to Expedia about these issues, I received an email from the resort at 5am on day two saying they'd refund our stay, but that I needed to check out by noon that same day or be charged for an additional night. I was off-property in Orlando at the time and couldn't make that window. When I returned, I told the front desk I'd be checking out the next morning at 11am (making it 3 nights total), and they simply said "ok" — no objection, no mention that this would affect the refund. Despite that, I was billed for the full 5 nights. When I called to dispute it, they claimed that because I didn't check out on the exact day specified in their 5am email, they were no longer honoring the refund. Between the false advertising, dated amenities charged at a premium, and a resort that goes back on what its own staff acknowledged, I would not recommend staying here.

Reviewed on Aug 27, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

CA $2,427
per person
Oct 10 - Oct 17
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
9.2/10 Wonderful! (584 reviews)
The Hotel Zamora

The Hotel Zamora

CA $1,430
per person
Oct 5 - Oct 12
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.8/10 Excellent! (391 reviews)
Highly recommend, friendly staff great hotel.

Reviewed on Aug 31, 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 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

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.

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.

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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.

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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.

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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

Kompose Boutique Hotel

965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
CA $56
CA $93 total
Sep 2 - Sep 3
includes taxes & fees
Kompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
CA $155
CA $211 total
Sep 3 - Sep 4
includes taxes & fees
Tropical Beach Resorts
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
CA $176
CA $238 total
Sep 8 - Sep 9
includes taxes & fees
9.4/10 Exceptional! (2,528 reviews)
"The room was clean and staff are nice. I love the breakfast buffet, there’s a lot of food than I thought. Overall it’s perfect and I will still choose to stay there if I come back to AMI."

Reviewed on Sep 1, 2026

Compass Hotel by Margaritaville Anna Maria Sound
See all 14,311 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.

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 $1,036. 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.

Things to do

Taking in the views of another epic Siesta Key sunset!

Siesta Key Electric Bike Sunset Tour

CA $99
per adult
96% of travellers recommend
Siesta Key Electric Bike Sunset Tour
Mangroves, Manatees & a Hidden Beach Kayak Tour

Mangrove Tunnel & Manatee Kayak Eco-Tour

CA $82
per adult
94% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
Sarasota Guided Mangrove Tunnel Kayak Tour

Sarasota Guided Mangrove Tunnel Kayak Tour

CA $82
per adult
96% of travellers recommend
Sarasota Guided Mangrove Tunnel Kayak Tour
See all activities in Siesta Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.