Highpoint Vacation Packages

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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.
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Price was CA $1,513, price is now CA $1,027 per person
CA $1,027
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (1,196 reviews)
Loved the location and the roof top pool and bar!!

Reviewed on May 6, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $3,165, price is now CA $1,985 per person
CA $1,985
per person
Jul 20 - Jul 27
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
9.6/10 Exceptional! (932 reviews)
Wonderful hotel and staff

Reviewed on May 8, 2026

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
South Village
Price was CA $4,608, price is now CA $2,913 per person
CA $2,913
per person
Jun 20 - Jun 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.8/10 Exceptional! (339 reviews)
Need more staff at the Cabana Bar

Reviewed on May 2, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,910, price is now CA $1,873 per person
CA $1,873
per person
Jul 26 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (534 reviews)
It was actually perfect. Amazing beach, amazing spacious room. One of our new top picks for vacay spots.

Reviewed on Apr 30, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $3,481, price is now CA $2,414 per person
CA $2,414
per person
Jul 25 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (506 reviews)
The staff was so sweet and accommodating. Everything you could need for an overnight at the beach. Room by the road had traffic noise but we didn’t mind at all!

Reviewed on May 7, 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

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 $469 per night from May 25 to May 26
CA $469
CA $584 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (3,222 reviews)
This hotel is in the perfect location. The beach is so close and umbrellas and chaise lounges are set up daily for your use. If you want the convenience of the pool, the ocean view is still amazing. Everything is walkable from this hotel with plenty of restaurants, bars and shopping in both directions. ...

Reviewed on May 8, 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 $291 per night from Jun 7 to Jun 8
CA $291
CA $383 total
Jun 7 - Jun 8
includes taxes & fees
8.2/10 Very Good! (2,609 reviews)
This is the third time that I have stayed here and I am never disappointed.

Reviewed on May 8, 2026

Hilton Clearwater Beach Resort & Spa
Island Grand at TradeWinds

Island Grand at TradeWinds

4 out of 5
5500 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from May 21 to May 22
CA $208
CA $320 total
May 21 - May 22
includes taxes & fees
7.6/10 Good! (1,139 reviews)
Yes

Reviewed on May 8, 2026

Island Grand at TradeWinds
See all 16,836 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
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Highpoint vacation package cost?
Our Highpoint packages, which start at just CA $1,027, 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.

Discover the most popular places to visit in Highpoint

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

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
White sand and palm trees in 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

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

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 $51
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 $62
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.