Highpoint Vacations

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    Save up to ￥109,000 when you book a flight and hotel together*

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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
5/5(26 area reviews)

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 ￥58,786 per night from Jul 1 to Jul 2
￥58,786
￥72,726 total
Jul 1 - Jul 2
includes taxes & fees
9.4/10 Exceptional! (3,305 reviews)
"At first, they tried to put us in a room that was facing a parking garage when I had paid for a golf view king-size bed. Thank goodness I had my reservation pulled up on my phone. They said I requested and accessible room, but that was not true. When they finally gave me my room, I was extremely ..."

Reviewed on Jun 1, 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 ￥28,294 per night from Jun 18 to Jun 19
￥28,294
￥38,272 total
Jun 18 - Jun 19
includes taxes & fees
8.2/10 Very Good! (2,649 reviews)
"We did not enjoy this hotel as much as we expected. It’s a little older, rundown and needs an update. The rugs in the room did not look clean and looked very old. Also the crowd was not the classiest."

Reviewed on May 31, 2026

Hilton Clearwater Beach Resort & Spa
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
The price is ￥26,228 per night from Jun 28 to Jun 29
￥26,228
￥29,770 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (1,338 reviews)
"I went there to enjoy a beautiful day at the pool, chill and relax. But the pool, although it looked fine, was closed. We had to lay out on the beach which had brown dirty water. We wanted to swim and chill in the pool! Also I thought that breakfast was to be included, that may have my misunderstanding. ..."

Reviewed on May 31, 2026

The Westin Tampa Bay
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.

Frequently asked questions

How much does a Highpoint vacation package cost?
Our Highpoint packages, which start at just , 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

4.5/5(1,655 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
Fort De Soto Park

Fort De Soto Park

4.5/5(681 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
Salvador Dali Museum

Salvador Dali Museum

4.5/5(1,191 reviews)

Browse the surrealistic masterpieces of a world-famous Spanish painter in a remarkable building that perfectly suits the style of the art exhibits.

Salvador Dali Museum

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

￥5,829
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

￥5,757
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

￥7,051
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.