Harbour Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

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

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

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    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.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $1,519, price is now CA $996 per person
CA $996
per person
Jul 28 - Jul 31
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (506 reviews)
The staff was so sweet and accommodating. Everything you could need for an overnight at the beach. Room by the road had traffic noise but we didn’t mind at all!

Reviewed on May 7, 2026

The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Price was CA $1,634, price is now CA $1,104 per person
CA $1,104
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (2,602 reviews)
Stayed for 3 nights … room was clean, staff was super friendly and hotel is centrally Located. They also offer a complementary Shuttle anywhere within a 2 mile radius which was very helpful… will definitely stay again…

Reviewed on May 11, 2026

The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Price was CA $1,517, price is now CA $1,029 per person
CA $1,029
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,196 reviews)
Loved the location and the roof top pool and bar!!

Reviewed on May 6, 2026

Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Price was CA $1,635, price is now CA $1,143 per person
CA $1,143
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,245 reviews)
The 2 bedroom condo was very clean and updated. The walk to the beach was short and we didn't have to cross any busy streets just walked the small roads within the complex of other resort condos.

Reviewed on May 8, 2026

East Gulf Dockside Beach Homes

East Gulf Dockside Beach Homes

2.5 out of 5
Price was CA $1,804, price is now CA $1,270 per person
CA $1,270
per person
Jul 11 - Jul 18
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
No reviews

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

5 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

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from May 25 to May 26
CA $225
CA $256 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (1,298 reviews)
elevators not working, pool closed for renovations,noicy hallways ,only one electric charger for cars and always not available.

Reviewed on May 11, 2026

The Westin Tampa Bay
OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

3 out of 5
3001 University Center Dr Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from May 25 to May 26
CA $171
CA $194 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (2,241 reviews)
Nice breakfast options and the property was very clean

Reviewed on May 11, 2026

OASIS BAY SUITES, Tampa, Busch Gardens, USF
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 $196 per night from May 31 to Jun 1
CA $196
CA $225 total
May 31 - Jun 1
includes taxes & fees
8.6/10 Excellent! (2,629 reviews)
Stayed for 3 nights … room was clean, staff was super friendly and hotel is centrally Located. They also offer a complementary Shuttle anywhere within a 2 mile radius which was very helpful… will definitely stay again…

Reviewed on May 11, 2026

The Barrymore Hotel Tampa Riverwalk
See all 6,129 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
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Frequently asked questions

How much does a Harbour Island vacation package cost?
Custom build your Harbour Island vacation package from just CA $996. 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
100% 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
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

CA $92
per adult
100% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
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.