Bay Island Holidays

Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was €495, price is now €340 per person
€340
per person
23 Mar - 27 Mar
found 1 day ago
Return flight included
Boston (BOS) to Tampa (TPA)
No reviews
Great staff, very clean.

Reviewed on 11 Jan 2026

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Price was €885, price is now €601 per person
€601
per person
23 Mar - 27 Mar
found 1 day ago
Return flight included
Boston (BOS) to Sarasota (SRQ)
7/10 Good! (1,744 reviews)
Great place . Right by river walk. Can walk a mile all the way to aquarium and cruise ship port. Free coffee in the morning. I wish there are more eatery right by the hotel. But you can walk to other eatery by the river walk or in the downtown area.

Reviewed on 13 Jan 2026

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Beach Park
Price was €1,132, price is now €789 per person
€789
per person
23 Mar - 27 Mar
found 1 day ago
Return flight included
Boston (BOS) to Sarasota (SRQ)
8.6/10 Excellent! (1,751 reviews)
The staff is very accommodating and helpful. Parking is complimentary but a little confusing. Restaurant/bar is available on site. Rooms a comfortable, views of internal courtyard. Pool is currently inoperable. Exercise room and outdoor seating/ open play areas are nice as well

Reviewed on 12 Jan 2026

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

2.5 out of 5
Price was €664, price is now €505 per person
€505
per person
23 Mar - 27 Mar
found 1 day ago
Return flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (1,000 reviews)
Clean new hotel. Excellent breakfast. EV chargers. Would definitely stay here again.

Reviewed on 12 Jan 2026

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Price was €789, price is now €610 per person
€610
per person
23 Mar - 27 Mar
found 1 day ago
Return flight included
Boston (BOS) to Tampa (TPA)
8.4/10 Very Good! (2,509 reviews)
Many rooms including mine had no hot water. Even though the issue was reported, nothing was done about it. Took one cold shower the entire stay.

Reviewed on 12 Jan 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
Unbelievable sugar white sand beach, beautiful place to visit.

South Village

1 out of top 10 points of interest in this area

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

Find hotels in South Village

Top hotels in Bay Island

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 €87 per night from 14 Jan to 15 Jan
€87
14 Jan - 15 Jan
includes taxes & fees
9/10 Wonderful! (4,866 reviews)
Always looked and smelled very clean! Beds and pillows were extremely comfortable.

Reviewed on 7 Jan 2026

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 €159 per night from 15 Jan to 16 Jan
€159
15 Jan - 16 Jan
includes taxes & fees
9.2/10 Wonderful! (5,203 reviews)
Everything was good nice and clean

Reviewed on 8 Jan 2026

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 €219 per night from 20 Jan to 21 Jan
€219
20 Jan - 21 Jan
includes taxes & fees
9.4/10 Exceptional! (1,909 reviews)
Great, nice clean hotel. Booked a Duluxe balcony room facing the marina. The hotel is idealy located although nothing was really walkable outside of the hotel [other than] the FIsh House Bar/Restaurant] so a car is recommended to get you places. The breakfast at the hotel was fresh with a good variation ...

Reviewed on 6 Jan 2026

Compass Hotel by Margaritaville Anna Maria Sound
See all 13,905 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 €340. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.