Bay Isles Vacation Packages

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Top Holiday Package Deals in Bay Isles

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was CA $1,657, price is now CA $955 per person
CA $955
per person
Apr 11 - Apr 18
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (2,193 reviews)
Great place to stay! Friendly staff. Spacious suites. Pet friendly. Heated pool.

Reviewed on Jan 31, 2026

Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

2.5 out of 5
Price was CA $6,704, price is now CA $3,343 per person
CA $3,343
per person
Mar 28 - Apr 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sarasota (SRQ)
9.6/10 Exceptional! (45 reviews)
The room was exactly as shown, plenty of room to stretch out and we especially loved the end unit. Steps from the beach and shelling was perfect! Grounds were raked each morning with umbrellas taken down each day. Nice cushions on the lounge chairs, deck furniture and the beach towels were nice & fluffy. A great lil refrigerator, we would have liked a coffee maker, rather than a cappuccino and the coffees offered were strong. No microwave. Bathroom with a lovely rain-head was favorable. We definitely recommend and it is located in a desirable area.

Reviewed on Jan 24, 2026

Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Price was CA $2,137, price is now CA $1,136 per person
CA $1,136
per person
Apr 11 - Apr 18
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9/10 Wonderful! (1,156 reviews)
4 times I encountered cockroaches in the room. One time scurrying across my foot while in the bathroom. Doubtful I’ll ever come back here.

Reviewed on Feb 5, 2026

Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Price was CA $1,613, price is now CA $978 per person
CA $978
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (496 reviews)
The room was clean. Comfortable bed. Kitchenette. Beautiful view of the water. Can watch the birds. Close to stores, restaurant, St. Pete beach, Tampa bay, and old Tampa bay, and other sites. The city of St. Petersburg and Tampa.

Reviewed on Jan 24, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $4,937, price is now CA $3,107 per person
CA $3,107
per person
Mar 24 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9.2/10 Wonderful! (480 reviews)
Such a cute cottage. Great location and friendly staff.

Reviewed on Feb 4, 2026

Bay Isles Hotel Deals

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
4675 N Tamiami Trl Sarasota FL
Fully refundable
The price is CA $119 per night from Feb 11 to Feb 12
CA $119
CA $135 total
Feb 11 - Feb 12
includes taxes & fees
8.4/10 Very Good! (2,246 reviews)
The room was fine and recently

Reviewed on Feb 3, 2026

Golden Host Resort - Sarasota
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 $125 per night from Feb 8 to Feb 9
CA $125
CA $158 total
Feb 8 - Feb 9
includes taxes & fees
9/10 Wonderful! (4,975 reviews)
I love staying here when I’m in Sarasota. The rooms are efficient. The work out facility is outstanding with circuit training, free weights, Peloton, stair master, tread. The breakfast is plentiful. The staff are friendly. And the price is excellent. A great value. I look forward to my next ...

Reviewed on Feb 5, 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 CA $273 per night from Feb 8 to Feb 9
CA $273
CA $344 total
Feb 8 - Feb 9
includes taxes & fees
9.2/10 Wonderful! (5,268 reviews)
Nice room and location!

Reviewed on Jan 31, 2026

Tropical Beach Resorts
See all 14,333 properties in Bay Isles
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 Isles vacation package cost?
Get your credit card ready, because a trip to Bay Isles starts from an affordable CA $955. When you bundle your hotels, flights and car rentals into a package, you'll score great deals.
How do I get a cheap travel package to Bay Isles?
Think of all the awesome things you could do in Bay Isles with a wad of extra cash in your wallet. Watch your savings stack up when you combine your travel bookings into a Bay Isles vacation package. You have plenty of choice when you book your trip with Expedia too. In fact, you can pick from over 550 air carriers and 1,000,000 properties across the globe. Whether you're taking off with the entire family or embarking on a solo adventure, exploring Bay Isles is better with a package.
What are the top hotels in Bay Isles?
When it comes to comfy places to stay in Bay Isles, you can't go past The Beach On Longboat Key #221s Resort By Rva. Look up our offers and score a great price.
How far in advance should I book my Bay Isles vacation?
Savvy travelers book early. Air carriers generally advertise flight tickets nearly 12 months in advance, and this is when you can pick up some rock-bottom prices. Boss just told you to use up all your vacation days next week? That's alright! Expedia are never short on fantastic bargains to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Bay Isles travel package include?
Choose from a combination of hotels, flights and rental cars. Once you've made your booking, you can add the fun stuff like experiences and activities. Want to pick your airfare class? That's also easy to do. The choice is all yours when it comes to crafting your ideal Bay Isles escape.
What should I know before booking a Bay Isles travel package?
A travel package can be tailored to your budget and is an easy way to stretch your hard-earned dollars. What you include is your call. Rental cars, hotels and flights — come up with a combination that suits your style.
Can I choose my airline with a Bay Isles Expedia vacation package?
Yes, the choice is yours. We offer more than 550 airlines across the globe, so you can design your Bay Isles vacation according to your budget and style.
If I'm not able to travel, can I cancel my Bay Isles vacation package?
It's good to know that you can cancel your Bay Isles booking if your plans have been upended. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Things to do

Sarasota - Clear Kayak LED Night Glass Bottom Tour

Sarasota - Clear Kayak LED Night Glass Bottom Tour

CA $90
per adult
80% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour

CA $90
per adult
84% of travellers recommend
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

CA $137
per adult
Anna Maria Island & Bradenton Beach Parasailing Tour
See all activities in Longboat Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.