Harbour Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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.
The Don CeSar

The Don CeSar

4 out of 5
Price was CA $2,038, price is now CA $1,407 per person
CA $1,407
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (1,173 reviews)
I have one word, WOW!!! You need to go and experience this amazing place for yourself!!!!!!

Reviewed on Jun 19, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,698, price is now CA $1,601 per person
CA $1,601
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,647, price is now CA $1,681 per person
CA $1,681
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (526 reviews)
Beautiful facility. Perfect for families close to all the beaches and fun. Can't wait to return for our next visit!

Reviewed on Jun 18, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,930, price is now CA $1,948 per person
CA $1,948
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (552 reviews)
The staff was very kind and accommodating. We will definitely look to book again.

Reviewed on Jun 19, 2026

The Marker

The Marker

2 out of 5
Price was CA $3,512, price is now CA $2,392 per person
CA $2,392
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
6/10 (3 reviews)
There was no staff due to it being brand new! The owner Jeff was great and very polite and went out of his way to make us feel welcome and valued! It was very quiet and comfortable for my family. Only about a two block walk to the beach but being in the bay was beautiful to wake up to!

Reviewed on Apr 12, 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

Downtown Tampa

4 out of top 10 points of interest in this area
4.5/5(56 area reviews)

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.

Find hotels in Downtown Tampa

Harbour Island Hotel Deals

Westin Tampa Downtown Waterside

Westin Tampa Downtown Waterside

4 out of 5
725 S Harbour Island Blvd Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $228 per night from Jul 3 to Jul 4
CA $228
CA $309 total
Jul 3 - Jul 4
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Great hotel, currently under renovation, sure it will be fabulous! Great location, restaurants, staff was so kind. Great stay!"

Reviewed on Jun 19, 2026

Westin Tampa Downtown Waterside
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
111 W Fortune St Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Jul 6 to Jul 7
CA $154
CA $177 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (2,641 reviews)
"very good location, well kept public areas and nice bar and pool"

Reviewed on Jun 21, 2026

The Barrymore Hotel Tampa Riverwalk
The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
4860 West Kennedy Boulevard Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jul 5 to Jul 6
CA $173
CA $196 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (1,820 reviews)
"Everything was very clean and ran smoothly. Common areas were nice. However, beds have been an issue. We stayed here early 2025 and one of the double/queen beds had a dip in the mattress so large you could have literally sat a basketball in the hole. We turned the mattress so the hole was closer ..."

Reviewed on Jun 17, 2026

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
See all 6,105 properties in Harbour 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Harbour Island vacation package cost?
Custom build your Harbour Island vacation package from just CA $1,407. 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.

Discover the most popular places to visit in Harbour Island

Busch Gardens Tampa Bay

Busch Gardens Tampa Bay

4.5/5(79 reviews)

Exotic animals and thrill rides all on the one site at this theme park and zoo designed for the whole family.

Busch Gardens Tampa Bay
Tampa_RaymondJamesStadium_503050_03

Raymond James Stadium

4.5/5(30 reviews)

Catch an event at Raymond James Stadium during your trip to Tampa. Attend a football game or simply enjoy the top-notch restaurants while you're in the area.

Raymond James Stadium
Tampa Riverwalk

Tampa Riverwalk

4.5/5(93 reviews)

Walk, bike or rollerblade along Tampa’s waterside neighborhood, with public art, museums, restaurants and more attractions right on the waterfront.

Tampa Riverwalk

Things to do

The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

CA $62
per adult
94% of travellers recommend
Pirate Adventure Cruise - John's Pass
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $51
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $51
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
See all activities in Tampa
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.