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 $1,096 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.
Zoo House Down Town Tampa

Zoo House Down Town Tampa

2.5 out of 5
Riverbend
Price was CA $822, price is now CA $486 per person
CA $486
per person
Apr 10 - Apr 15
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
2/10 (1 review)
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was CA $1,657, price is now CA $955 per person
CA $955
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (2,193 reviews)
Great place to stay! Friendly staff. Spacious suites. Pet friendly. Heated pool.

Reviewed on Jan 31, 2026

Crystal Palms Beach Resort

Crystal Palms Beach Resort

3.5 out of 5
Sunshine Beach
Price was CA $2,779, price is now CA $1,663 per person
CA $1,663
per person
Apr 11 - Apr 18
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (2,355 reviews)
Furniture was very old/ dirty and couch was broken.

Reviewed on Jan 14, 2026

Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Price was CA $1,617, price is now CA $978 per person
CA $978
per person
Apr 11 - Apr 18
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (496 reviews)
The room was clean. Comfortable bed. Kitchenette. Beautiful view of the water. Can watch the birds. Close to stores, restaurant, St. Pete beach, Tampa bay, and old Tampa bay, and other sites. The city of St. Petersburg and Tampa.

Reviewed on Jan 24, 2026

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Price was CA $2,295, price is now CA $1,469 per person
CA $1,469
per person
Apr 11 - Apr 18
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
Great room, great view and beach. Wonderful staff. I would stay here again.

Reviewed on Feb 6, 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
Curtis Hixon Waterfront Park

Downtown Tampa

5 out of top 10 points of interest in this area
4.5/5(55 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 Waterside

The Westin Tampa Waterside

4 out of 5
725 S Harbour Island Blvd Tampa FL
The price is CA $380 per night from Feb 22 to Feb 23
CA $380
CA $480 total
Feb 22 - Feb 23
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Nice location! Morning walks looking at the water was great

Reviewed on Jan 20, 2026

The Westin Tampa Waterside
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 $98 per night from Mar 8 to Mar 9
CA $98
CA $111 total
Mar 8 - Mar 9
includes taxes & fees
6.2/10 (3,905 reviews)
Great breakfast, deposits were different amounts for 2 different stays which was odd but hotel was fine for 1 night

Reviewed on Feb 2, 2026

Ramada by Wyndham Tampa Westshore Airport South
Quality Inn Airport - Cruise Port

Quality Inn Airport - Cruise Port

2.5 out of 5
1020 S Dale Mabry Hwy Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Mar 8 to Mar 9
CA $161
CA $183 total
Mar 8 - Mar 9
includes taxes & fees
8/10 Very Good! (1,389 reviews)
The room was spotless and the staff was courteous

Reviewed on Feb 1, 2026

Quality Inn Airport - Cruise Port
See all 6,034 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
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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 $486. 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 showing rides

Busch Gardens Tampa Bay

4.5/5(77 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(29 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(92 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 StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $39
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

CA $52
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

CA $51
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
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.