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Highpoint 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

Your Highpoint Vacation

Say bye-bye to the stress of planning and hello to a Highpoint vacation package. With everything organized before you take off, you can focus on discovering the best of this city, starting with Downtown Dunedin, which is great for shopping, walking and gift and craft shops. Any trip to Highpoint needs a well-crafted itinerary. Fill yours with big-name attractions like Ruth Eckerd Hall, Eddie C. Moore Softball Complex and Bright House Field. A few clicks is all it takes to put together the perfect Highpoint vacation on Expedia.

The Latest Highpoint Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 26 - Jan 30

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    4 nights
    4.0 star property
    9.6/10 - Exceptional (1,317 reviews)
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $1,395
    CA $912
    per traveller
    found 20 hours ago
    Ocean Club Treasure Island Hotel
  • Jan 14 - Jan 17

    voco Sarasota by IHG + Flight

    Central Sarasota
    3 nights
    3.5 star property
    9.0/10 - Wonderful (1,000 reviews)
    Roundtrip • Toronto (YTO) - Tampa (TPA)
    YTZ - TPA • 1 stop TPA - YYZ • Nonstop
    CA $1,375
    CA $920
    per traveller
    found 1 day ago
    voco Sarasota by IHG
  • Jan 14 - Jan 17

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    3 nights
    3.0 star property
    9.4/10 - Exceptional (623 reviews)
    "What a treat for us Minnesotans!!! Special place to stay. Clean, comfy, and cozy! We stayed in the Violet Cottage. Staff allowed us to hang for a bit on the beach (plus parking for our rental) after check-out. There is even a shower available for this exact purpose, which is extra handy and appreciated. Thank you! We hope to be back some day!"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YTO) - Tampa (TPA)
    YTZ - TPA • 1 stop TPA - YYZ • Nonstop
    CA $1,702
    CA $1,180
    per traveller
    found 1 day ago
    Cedar Cove Resort and Cottages
  • Jan 28 - Feb 1

    Hotel Flor Tampa Downtown, Tapestry Collection by Hilton + Flight

    Downtown Tampa
    4 nights
    4.0 star property
    8.6/10 - Excellent (965 reviews)
    Roundtrip • Toronto (YTO) - Tampa (TPA)
    YTZ - TPA • 1 stop TPA - YYZ • Nonstop
    CA $2,243
    CA $1,612
    per traveller
    found 1 day ago
    Hotel Flor Tampa Downtown, Tapestry Collection by Hilton
  • Jan 28 - Feb 1

    Hotel South Tampa & Suites + Flight

    Virginia Park
    4 nights
    3.0 star property
    8.6/10 - Excellent (1,978 reviews)
    "Our stay at Hotel South Tampa was great, the staff was wonderful and the amenities were great. I will absolutely stay again."
    Reviewed November 13, 2026
    Roundtrip • Toronto (YTO) - Tampa (TPA)
    YTZ - TPA • 1 stop TPA - YYZ • Nonstop
    CA $1,325
    CA $953
    per traveller
    found 1 day ago
    Hotel South Tampa & Suites

Where to stay in Highpoint

Find the best Highpoint areas and neighborhoods for the activities you enjoy most.

Downtown St. Petersburg

Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.

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.

Sunset Beach

Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like Sunset Beach and St. Petersburg - Clearwater Beaches.

Sand Key

While visiting Sand Key, you might make a stop by sights like Belleair Beach and Sand Key Park.

Sunshine Beach

If you're spending some time in Sunshine Beach, St. Petersburg - Clearwater Beaches and St. Petersburg Municipal Beach at Treasure Island are top sights worth seeing.

Highpoint Hotel Deals

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.

Frequently Asked Questions

How much does a Highpoint vacation package cost?

Our Highpoint packages, which start at just CA $912, are the easiest way to save precious money. Select your favorite hotels, flights and more to create your dream escape.

How do I get a cheap travel package to Highpoint?

Combining your flight and hotel with Expedia won't just save you time — it'll save you a few dollars too. A Highpoint vacation package makes it simple to arrange the ideal trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your schedule won't be hard. In addition to that, we've got over 1,000,000 hotels globally to select from. Now that's choice! No matter who you are, Expedia will help show you the world.

Where should I stay in Highpoint?

With fascinating attractions like Tampa Bay Grand Prix and Cove Cay Golf Club in this area, look for a hotel located near them. Feather Sound Country Club is another sight that visitors flock to.

What are the top hotels in Highpoint?

If it's your very first time in Highpoint, make a reservation at Holiday Inn Express Clearwater East - Icot Center, an IHG Hotel or Intown Suites Extended Stay Clearwater Fl. Both offer comfortable beds and are popular options with many savvy travelers.

How far in advance should I book my Highpoint vacation?

It's always wise to book early. Airlines generally release flights nearly 12 months in advance, and this is an ideal opportunity to pick up some of the cheapest prices. Boss just told you to take all your vacation days next week? That's fine too — Expedia are never short of fantastic bargains to send you on the getaway of your dreams, at an affordable price.

What does an Expedia Highpoint travel package include?

Flights, hotels and car rentals — we connect you to all the best deals. All you have to do is pick and choose your ideal combination. Once you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to create an awesome Highpoint escape.

What should I know before booking a Highpoint travel package?

Bundling your bookings into a Highpoint vacation package is the most convenient way to organize your trip. Not only that, you'll save when you combine your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?

Can I choose my airline with a Highpoint Expedia vacation package?

Yes, of course. We have more than 550 partner airlines worldwide, so select the carrier that best fits your travel preferences.

If I'm not able to travel, can I cancel my Highpoint vacation package?

It's impossible to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Highpoint vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to find out more.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.