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.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,240, price is now CA $1,208 per person
CA $1,208
per person
Jan 21 - Jan 28
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)
Nice property, clean pool. Units were not sound roof at all, you could hear every little noise from each room and other units, but it did not ruin our time there.

Reviewed on Nov 10, 2026

Westwinds Waterfront Resort

Westwinds Waterfront Resort

3 out of 5
Save 100% on your flight
Price was CA $2,019, price is now CA $1,249 per person
CA $1,249
per person
Feb 1 - Feb 8
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (742 reviews)
It was a great location for the beach, dinner, and awesome spot to just hang out on the property! Beautiful beautiful place!!

Reviewed on Nov 9, 2026

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $1,913, price is now CA $1,209 per person
CA $1,209
per person
Jan 21 - Jan 28
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,532 reviews)
Nicely renovated. Clean and convenient.

Reviewed on Nov 10, 2026

La Tortuga Historic Downtown Pass A Grille

La Tortuga Historic Downtown Pass A Grille

4 out of 5
Pass-a-Grille
Price was CA $3,558, price is now CA $2,268 per person
CA $2,268
per person
Jan 23 - Jan 30
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (37 reviews)
Great location on 8th Ave. We loved being so close to the historic section.

Reviewed on Nov 8, 2026

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $2,144, price is now CA $1,375 per person
CA $1,375
per person
Jan 21 - Jan 28
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,266 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
A cityscape with tall buildings, palm trees, and a fountain.

Downtown Tampa

3 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.

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 $191 per night from Nov 23 to Nov 24
CA $191
CA $267 total
Nov 23 - Nov 24
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"$249 a night for a broken, neglected room. The closet door won’t stay open. The bathroom door either blocks you or shuts out your dog, which made mine bark. The bathroom outlet is loose, a clear sign this hotel is not cared for. The sign to 725 South points down an empty hallway. The restaurant is ..."

Reviewed on Nov 8, 2026

Westin Tampa Downtown Waterside
Four Points by Sheraton Suites Tampa Airport Westshore

Four Points by Sheraton Suites Tampa Airport Westshore

3 out of 5
4400 W Cypress St Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Nov 15 to Nov 16
CA $179
CA $203 total
Nov 15 - Nov 16
includes taxes & fees
Four Points by Sheraton Suites Tampa Airport Westshore
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
The price is CA $207 per night from Nov 23 to Nov 24
CA $207
CA $235 total
Nov 23 - Nov 24
includes taxes & fees
The Westin Tampa Bay
See all 6,063 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 $1,208. 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

Crystal River: Manatee River Boat Tour with Naturalist Guide

Crystal River: Manatee River Boat Tour with Naturalist Guide

CA $41
per adult
Crystal River: Manatee River Boat Tour with Naturalist Guide
Tampa: Pirate Adventure Cruise

Tampa: Pirate Adventure Cruise

CA $59
per adult
Tampa: Pirate Adventure Cruise
Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle

Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle

CA $57
per traveller
100% of travellers recommend
Florida's Must-See Sights: Self-Guided Driving Audio Tour Bundle
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.