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.

Top Holiday Package Deals in Highpoint

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was CA $1,589, price is now CA $1,051 per person
CA $1,051
per person
Sep 9 - Sep 16
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (2,333 reviews)
Super bueno y muy cerca de todo

Reviewed on Jun 15, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,513, price is now CA $1,524 per person
CA $1,524
per person
Sep 9 - Sep 16
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (526 reviews)
Beautiful facility. Perfect for families close to all the beaches and fun. Can't wait to return for our next visit!

Reviewed on Jun 18, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $1,795, price is now CA $1,170 per person
CA $1,170
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
No reviews
The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Price was CA $3,776, price is now CA $2,551 per person
CA $2,551
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Tampa (TPA)
8.2/10 Very Good! (556 reviews)
Excelente ubicación y 100% recomendado.

Reviewed on May 30, 2026

The Don CeSar

The Don CeSar

4 out of 5
Price was CA $2,041, price is now CA $1,412 per person
CA $1,412
per person
Aug 21 - Aug 26
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (1,165 reviews)
I have one word, WOW!!! You need to go and experience this amazing place for yourself!!!!!!

Reviewed on Jun 19, 2026

Where to stay in Highpoint

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

Highpoint Hotel Deals

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
The price is CA $236 per night from Jul 3 to Jul 4
CA $236
CA $268 total
Jul 3 - Jul 4
includes taxes & fees
8.6/10 Excellent! (1,372 reviews)
"Swimming pool was closed for our stay."

Reviewed on Jun 15, 2026

The Westin Tampa Bay
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 $367 per night from Jul 8 to Jul 9
CA $367
CA $471 total
Jul 8 - Jul 9
includes taxes & fees
9.4/10 Exceptional! (3,380 reviews)
"Very welcoming place. Staff is pleasant and attentive. Located within walking distance to local attractions."

Reviewed on Jun 18, 2026

Wyndham Grand Clearwater Beach
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 $278 per night from Jun 30 to Jul 1
CA $278
CA $370 total
Jun 30 - Jul 1
includes taxes & fees
8.2/10 Very Good! (2,695 reviews)
"Overall the hotel was very nice, the amenities were great, the staff were friendly. Check in was a little rough, but check out was a breeze. Cons: the air conditioner did not work very well, there was mold all over the corner of our room, and everything was incredibly expensive, especially for a ..."

Reviewed on Jun 19, 2026

Hilton Clearwater Beach Resort & Spa
See all 16,866 properties in Highpoint
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 Highpoint vacation package cost?
Our Highpoint packages, which start at just CA $1,051, 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.