Harbour Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Harbour Island
Price found within the past 48 hours. Click for updated prices.
Cedar Cove Resort and Cottages
CA $1,815
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (563 reviews)
Stayed for one night everything was in place very well thought off and cosy and very clean love the swing just out the door and seeing the shells all over and beach was amazing shower and beach chairs was in place staff was very friendly and had a home feeling I will be back
Reviewed on Aug 5, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
CA $1,066
per person
Oct 19 - Oct 24
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (1,113 reviews)
We had a really nice time but the hotel could use more amenities and longer hours for poo/bar.
Reviewed on Aug 7, 2026
ChartHouse Clearwater Beach Marina Hotel
CA $1,349
per person
Sep 18 - Sep 25
found 11 hours ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
9.6/10 Exceptional! (1,306 reviews)
Overall the hotel was just ok. The TV in the rooms do not stream or have cable channels, just very basic Samsung TV Channels. The floors on the property were always slippery with puddles of water everywhere. We had to be very careful walking the entire time. I would not return.
Reviewed on Aug 7, 2026
CW Hotel
CA $1,582
per person
Sep 18 - Sep 25
found 11 hours ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
9.6/10 Exceptional! (29 reviews)
Brand new hotel , we were there for the 1st night of opening so had to deal with all the new problems . Nice hotel I would definitely give them another try
Reviewed on Aug 8, 2026
Where to stay in Harbour Island
Find the best Harbour Island areas and neighborhoods for the activities you enjoy most. Learn more about Harbour Island
Downtown Tampa
4 out of top 10 points of interest in this area
Explore top attractions like the Florida Aquarium, Glazer Children's Museum, and Tampa Riverwalk, or indulge in the vibrant nightlife and dining scene in the River Arts District. Easily navigate the area with TECO Streetcar and HART public transportation.
Ybor City
Designated as a National Historic Landmark District, this Tampa neighborhood boasts the Ybor City Museum State Park and a variety of attractions like the Cigar Museum. Enjoy Florida's oldest restaurant, Columbia, and vibrant nightlife along 7th Avenue, easily accessible via TECO Line Streetcar.
Hyde Park
Historic homes and fine dining abound next to Downtown Tampa. Here it’s easy to develop a taste for the finer things in life.
Town 'n' Country
If you're spending some time in Town 'n' Country, Tampa Bay and Countryway Golf Club are top sights worth seeing.
Tampa Heights
While visiting Tampa Heights, you might make a stop by sights like Armature Works and Tampa Waterworks Park.
Harbour Island Hotel Deals
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
CA $201
CA $228 total
Aug 23 - Aug 24
includes taxes & fees
Four Points by Sheraton Suites Tampa Airport Westshore
4400 W Cypress St Tampa FL
Fully refundableReserve now, pay when you stay
CA $148
CA $168 total
Aug 16 - Aug 17
includes taxes & fees
8.4/10 Very good! (1,131 reviews)
"This is our second year staying here. My family and I love the hotel. Friendly staff and very clean facility."
Reviewed on Aug 7, 2026
OASIS BAY SUITES, Tampa, Busch Gardens, USF
3001 University Center Dr Tampa FL
Fully refundableReserve now, pay when you stay
CA $130
CA $148 total
Aug 21 - Aug 22
includes taxes & fees
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 Harbour Island vacation package cost?
Custom build your Harbour Island vacation package from just CA $902. Choose from any combination of rental cars, flights and hotels to put together the escape you've been dreaming about. Don't forget to add on some activities and experiences!
How do I get a cheap travel package to Harbour Island?
Booking a flight and hotel together with Expedia won't just save valuable time — it'll save you a nice amount too. A Harbour Island vacation package makes it easy to put together your ideal trip. With more than 550 airlines across the world to select from, finding convenient flights that fit your schedule won't be hard. On top of that, we've got over 1,000,000 hotels globally to choose from. Talk about choice! Whatever your budget, Expedia puts more of the world within your reach.
Where should I stay in Harbour Island?
Most travelers who visit Harbour Island put both Port of Tampa and Raymond James Stadium on their to-do lists. Why not reserve a hotel near these great attractions?
What are the top hotels in Harbour Island?
If it's comfort and convenience you're looking for, it's hard to beat The Westin Tampa Waterside. Spend your nights relaxing here and your days discovering Harbour Island's finest sights.
How far in advance should I book my Harbour Island vacation?
Reward yourself with the biggest variety at the cheapest prices by booking your vacation to Harbour Island nice and early. Airlines generally release flights anywhere up to a year in advance, so start your planning ASAP. That being said, Expedia is committed to providing you with the best bargains around, so it's always a good time to book your dream vacation!
What does an Expedia Harbour Island travel package include?
Flights, hotels and a reliable car for all your fun road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you've made your booking, add on a few tours and activities and watch your savings grow. When it comes to creating your Harbour Island trip, the choice is all yours!
What should I know before booking a Harbour Island travel package?
We already have low prices. However, you'll grab an even better deal when you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and a great range of choice.
Can I choose my airline with a Harbour Island Expedia vacation package?
Expedia has access to more than 550 partner airlines worldwide, so you definitely can. Just pick the airline you want and put together your ideal Harbour Island escape.
If I'm not able to travel, can I cancel my Harbour Island vacation package?
If your travel plans in Harbour Island have been upended, it's a relief to know that it is possible to cancel or amend your booking. If you booked within the last 24 hours, you may be able to get a refund. If your booking is older than that, your airline, hotel or car rental company may impose a fee. For more information, check our Customer Service Portal.
Things to do
Pirate Adventure Cruise - John's Pass
CA $69
per adult
94% of travellers recommend
The Official Downtown Tampa Ghost Tour
CA $42
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.