Bay Island Holidays

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

Siesta Key Village is known for its stunning beaches, and with sights like Siesta Key Beach and Siesta Key Farmers Market, you won't get bored spending a day wandering around this part of Siesta Key.

Find hotels in Siesta Key Village
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

If you're spending some time in South Village, Safe Harbor Siesta Key and Crescent Beach are top sights worth seeing.

Find hotels in South Village
Default Image

Aloha Kai

While there might not be top attractions in Aloha Kai, you can explore the larger area and discover places like Siesta Key Beach and Crescent Beach.

Find hotels in Aloha Kai
Default Image

Bailey Hall

Bailey Hall might not have many top sights, but Siesta Key Beach and Lido Beach are two attractions nearby that you can check out.

Find hotels in Bailey Hall
Default Image

Point of Rocks

While Point of Rocks isn't home to many top sights, Siesta Key Beach and Point of Rocks are some notable places to visit nearby.

Find hotels in Point of Rocks

Top hotels in Bay Island

Kompose Boutique Hotel

Kompose Boutique Hotel

965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
S$82
27 Sept - 28 Sept
includes taxes & fees
Kompose Boutique Hotel
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
S$217
20 Sept - 21 Sept
includes taxes & fees
9.4/10 Exceptional! (2,549 reviews)
"Great location and place to stay,I’m already planning on going back next summer"

Reviewed on 12 Sept, 2026

Compass Hotel by Margaritaville Anna Maria Sound
Tropical Beach Resorts

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
S$226
27 Sept - 28 Sept
includes taxes & fees
Tropical Beach Resorts
See all 14,279 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 holiday package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Bay Island from just . And the more you bundle, the more money you save. The holiday 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 holiday 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 holiday makers book a hotel around this impressive tourist attraction.
What are the top hotels in Bay Island?
Get your holiday 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 holiday?
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 holiday package?
With a holiday 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 holiday package?
Whether it's your hotel, flight or rental car, you can cancel or change it. Locked in your Bay Island holiday 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

Lido Key: Self-Guided Paddleboard Rental

Lido Key: Self-Guided Paddleboard Rental

S$55
per adult
100% of travellers recommend
Lido Key: Self-Guided Paddleboard Rental
Sarasota - Clear Kayak LED Night Glass Bottom Tour

Sarasota - Clear Kayak LED Night Glass Bottom Tour

S$83
per adult
78% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
Taking in the views of another epic Siesta Key sunset!

Siesta Key Electric Bike Sunset Tour

S$91
per adult
96% of travellers recommend
Siesta Key Electric Bike Sunset 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.