Harbor Hills Vacation Packages

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Price found within the past 48 hours. Click for updated prices.
  • Classic Double Room, Bay View
    Aug 15 - Aug 21

    CW Hotel + Flight

    Clearwater Beach
    6 nights
    2.0 star property
    Roundtrip • Montreal (YUL) - Tampa (TPA)
    YUL - TPA • Nonstop TPA - YUL • Nonstop
    CA $3,308
    CA $1,908
    per traveller
    found 6 hours ago
    CW Hotel
  • Exterior
    Jul 1 - Jul 12

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    11 nights
    3.0 star property
    9.2/10 - Wonderful (517 reviews)
    "It was amazing, we stayed at the Flamingo Suite, all was clean and tidy. The cottage has a great location close to all restaurants either south or north of the island since it is situated kind of in the middle of the island. The staff was so nice and understanding. So conveniently located right on the beach. Overall a great experience."
    Reviewed May 25, 2026
    Roundtrip • Montreal (YUL) - Tampa (TPA)
    YUL - TPA • 1 stop TPA - YUL • 1 stop
    CA $4,387
    CA $2,286
    per traveller
    found 0 hours ago
    Cedar Cove Resort and Cottages
  • 2 bedrooms, memory foam beds, in-room safe, blackout drapes
    Jun 28 - Jul 11

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    13 nights
    4.0 star property
    9.6/10 - Exceptional (979 reviews)
    "The room(s) was outstanding. Everything you needed, just like being at home. The pool was small and to many kids playing ball, that made it not useable. The beach access was more of a walk than what we wanted, no chairs on the beach that were provided by the club & no restaurants on site."
    Reviewed May 25, 2026
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $4,985
    CA $3,010
    per traveller
    found 1 day ago
    Ocean Club Treasure Island Hotel
  • Property grounds
    Jul 5 - Jul 11

    The Residences at Siesta Key Beach by Hyatt Vacation Club + Flight

    South Village
    6 nights
    3.5 star property
    9.6/10 - Exceptional (354 reviews)
    "Amazing place for a family vacation !"
    Reviewed May 26, 2026
    Roundtrip • Montreal (YUL) - Tampa (TPA)
    YUL - TPA • Nonstop TPA - YUL • Nonstop
    CA $5,604
    CA $3,536
    per traveller
    found 1 day ago
    The Residences at Siesta Key Beach by Hyatt Vacation Club
  • Grand Suite, 3 Bedrooms, Ocean View | Terrace/patio
    Jun 28 - Jul 11

    The Avalon Club + Flight

    Clearwater Beach
    13 nights
    4.0 star property
    9.4/10 - Exceptional (546 reviews)
    "Definitely I go same place next time"
    Reviewed May 24, 2026
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $7,630
    CA $4,969
    per traveller
    found 1 day ago
    The Avalon Club

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
Pass-a-Grille

Pass-a-Grille

1 out of top 10 points of interest in this area

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

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 $518 per night from Jun 2 to Jun 3
CA $518
CA $640 total
Jun 2 - Jun 3
includes taxes & fees
9.4/10 Exceptional! (3,289 reviews)
"This was our second stat with Wyndham Grand at Clearwater Beach and it was not disappointing. We had very early flight and I ask the hotel if they could have our room ready earlier. They did not promise anything but when we arrived our room was ready and on the top, it was upgraded to the full Gulf ..."

Reviewed on May 26, 2026

Wyndham Grand Clearwater Beach
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 $227 per night from Jun 7 to Jun 8
CA $227
CA $258 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (1,327 reviews)
"Amazing stay! Would stay here again"

Reviewed on May 26, 2026

The Westin Tampa Bay
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 $245 per night from Jun 18 to Jun 19
CA $245
CA $332 total
Jun 18 - Jun 19
includes taxes & fees
8.2/10 Very Good! (2,630 reviews)
"Overall was good but the room I rented for $417 they didn’t have it ready for me. They gave me a $200 room I didn’t get no money back"

Reviewed on May 26, 2026

Hilton Clearwater Beach Resort & Spa
See all 14,679 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
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Frequently asked questions

How much does a Harbor Hills vacation package cost?
Less than you might think — from a tempting , 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

Aerial view of the pink-tinged waters reflecting the vibrant sunset hues next to the John's Pass Village & Boardwalk, Treasure Island, Florida, United States.

John's Pass Village & Boardwalk

4.5/5(141 reviews)

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

John's Pass Village & Boardwalk
Aerial sunset view of Clearwater beach and Sand key in Western Florida on the Mexican Gulf coast with vacation homes, hotels and bridges connecting

Clearwater Beach

4.5/5(5 reviews)

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

Fort De Soto Park

4.5/5(28 reviews)

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

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $51
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
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
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

CA $61
per adult
100% of travellers recommend
Pirate Adventure Cruise - John's Pass
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.