Harbor Hills Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Harbor Hills

Price found within the past 48 hours. Click for updated prices.
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
per person
Aug 28 - Sep 3
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9/10 Wonderful! (1,025 reviews)
The breakfast was incredible and the staff were awesome! The sidewalk door was not working at night and we had to walk all the way around the building, but it was fixed the next morning.

Reviewed on Jul. 24, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
per person
Sep 13 - Sep 20
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,008 reviews)
Great choice..I will stay again for sure

Reviewed on Jul. 21, 2025

The Avalon Club

The Avalon Club

4 out of 5
per person
Aug 25 - Aug 29
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (430 reviews)
Great property and location

Reviewed on Jul. 21, 2025

Barsala At The Wayland Condos

Barsala At The Wayland Condos

4 out of 5
per person
Aug 28 - Sep 3
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
7.6/10 Good! (10 reviews)
My little getaway was amazing!!! The studio was beautiful, had everything we needed I wasn't expecting a full kitchen with baking utensils as well. We had a blast the view was incredible. I loved the outside setup near the pool as well. Will definitely be booking another getaway real soon!!

Reviewed on Jun. 10, 2025

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
8.6/10 Excellent! (2,143 reviews)
The hotel rooms inside were super nice and right by the beach.

Reviewed on Jul. 25, 2025

Where to stay in Harbor Hills

Find the best Harbor Hills areas and neighborhoods for the activities you enjoy most. Learn more about Harbor Hills
Default Image

Pass-a-Grille

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotels in Pass-a-Grille

Harbor Hills Hotel Deals

Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from Aug 12 to Aug 13
CA $231
CA $315 total
Aug 12 - Aug 13
includes taxes & fees
8/10 Very Good! (2,051 reviews)
"Location we could pretty much walk anywhere. Beach was clean and beautiful could watch the sunset every night."

Reviewed on Jul. 24, 2025

Hilton Clearwater Beach Resort & Spa
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd, Tampa, FL
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Aug 3 to Aug 4
CA $173
CA $196 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (2,015 reviews)
"The property was very comfortable and well kept. The food there was also great as well! Definitely a go to if you’re in the Tampa area."

Reviewed on Jul. 24, 2025

Hotel Alba, Tapestry Collection by Hilton
Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $392 per night from Aug 3 to Aug 4
CA $392
CA $497 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (2,429 reviews)
"Great stay from start to finish. Super clean and well maintained. Great employees, service was excellent, food and drinks were great as well."

Reviewed on Jul. 25, 2025

Wyndham Grand Clearwater Beach
See all 13,801 properties in Harbor Hills
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 Harbor Hills vacation package cost?
Less than you might think — from a tempting CA $788, as a matter of fact! By bundling hotels, flights and car rentals into your own customized package, your getaway to Harbor Hills is just clicks away.
How do I get a cheap travel package to Harbor Hills?
Crafting your own Harbor Hills vacation package with Expedia is a smart way to save. We offer access to over 550 air carriers and 1,000,000 properties globally. With such a fantastic range to pick from, you'll have no trouble pulling together your ideal getaway.
Where should I stay in Harbor Hills?
With so much to explore in Harbor Hills, we recommend you book a room in a hotel close to its attractions. Largo Medical Center, Pinellas Trail and Largo Mall are some interesting ones to put on your must-see list.
What are the top hotels in Harbor Hills?
When it comes to comfortable places to stay in Harbor Hills, you can't go past Newly Renovated Florida Home Minutes From Indian Rocks And Clearwater Beach. Check out our offers and score a bargain.
How far in advance should I book my Harbor Hills vacation?
While not all airlines release tickets early, you can usually start comparing international fares on Expedia up to 12 months in advance. This is the time when you'll bag some incredible bargains. If you've left everything to the last minute, you might get lucky. Discounted prices occasionally become available a few weeks before departure.
What does an Expedia Harbor Hills travel package include?
With Expedia, you can choose any combination of hotels, car rentals and flights to create your ideal Harbor Hills travel package. Once you've made your booking, you can add on all the fun stuff like tours and activities. Don't forget — the more you bundle, the more cash you'll save!
What should I know before booking a Harbor Hills travel package?
You can look forward to saving with an Expedia travel package. Combine your flights, rental cars and hotels and pick up exciting discounts. You're not limited to hotels, however. We've got island resorts, city apartments and just about everything in between!
Can I choose my airline with a Harbor Hills Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Harbor Hills vacation package?
Your situation can change in a flash, so yes. You may be able to cancel or amend your Harbor Hills vacation package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still make the necessary changes, but your car rental company, hotel or airline may charge a fee. Looking for more information? Look up our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Harbor Hills

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area, or check out its lively bars.

John's Pass Village & Boardwalk
Clearwater Beach

Clearwater Beach

Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach
Fort De Soto Park which includes a sandy beach

Fort De Soto Park

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park

Things to do

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

CA $44
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

CA $51
per adult
94% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
Sea Screamer boat in Orlando

Day Trip to Clearwater Beach with Sea Screamer Ride

CA $171
per adult
90% of travellers recommend
Day Trip to Clearwater Beach with Sea Screamer Ride
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.