Harbour Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $1,096 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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Top Holiday Package Deals in Harbour Island

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,631, price is now CA $1,076 per person
CA $1,076
per person
Apr 26 - May 3
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
8.6/10 Excellent! (68 reviews)
The property was perfect for pets. Big space to walk and off the main road.

Reviewed on Mar 23, 2026

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Town 'n' Country
Price was CA $1,995, price is now CA $1,260 per person
CA $1,260
per person
May 9 - May 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
2/10 (4 reviews)
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Price was CA $2,013, price is now CA $1,312 per person
CA $1,312
per person
May 7 - May 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (1,193 reviews)
Everything was great

Reviewed on Mar 23, 2026

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was CA $1,786, price is now CA $1,173 per person
CA $1,173
per person
May 9 - May 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
7.4/10 Good! (27 reviews)
This resort is absolutely amazing I didn't eat breakfast there but I'm sure it was awesome because everything else there was awesome

Reviewed on Mar 16, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $3,005, price is now CA $2,018 per person
CA $2,018
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (515 reviews)
Our family had a wonderful 4-night stay at this well kept hotel. The apartment was spacious, very clean, had nice amenities, and the hotel is conveniently located just steps from the beach. We recommend and would be happy to stay there again.

Reviewed on Mar 13, 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

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

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
200 N Ashley Dr Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Apr 5 to Apr 6
CA $227
CA $260 total
Apr 5 - Apr 6
includes taxes & fees
7/10 Good! (1,801 reviews)
I had a child in the next room that was nonstop for over 5 hours. I asked to move my room, and I felt that the woman who was working the night shift was completely unsympathetic to my situation. I was speaking to someone else, and she injected herself into our conversation. I would only want people ...

Reviewed on Mar 26, 2026

Hotel Tampa Riverwalk
Ramada by Wyndham Tampa Westshore Airport South

Ramada by Wyndham Tampa Westshore Airport South

3 out of 5
1200 N Westshore Blvd Tampa FL
The price is CA $128 per night from Mar 30 to Mar 31
CA $128
CA $146 total
Mar 30 - Mar 31
includes taxes & fees
6.2/10 (4,199 reviews)
I'm shocked that this is a Wyndham property. It is very run down and felt dodgy and dirty. It is terribly outdated and overpriced for what it is. Shuttle bus was supposed to come in 30 min and we waited over an hour and finally took a taxi. The staff was friendly - none of this is their fault. I ...

Reviewed on Mar 27, 2026

Ramada by Wyndham Tampa Westshore Airport South
Sailport Waterfront Suites

Sailport Waterfront Suites

3.5 out of 5
2506 N Rocky Point Dr Tampa FL
The price is CA $190 per night from Apr 2 to Apr 3
CA $190
CA $241 total
Apr 2 - Apr 3
includes taxes & fees
8.4/10 Very Good! (4,973 reviews)
Liked heated pool and restaurant attached

Reviewed on Mar 26, 2026

Sailport Waterfront Suites
See all 6,014 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 $1,076. 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 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
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

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 $50
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 $91
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.