Highpoint Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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

Our guide on 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

As you view this neighborhood’s iconic pink hotel it feels as if you’ve crossed into the past. Find beautiful beaches and serene enjoyment here.

Find hotels in Pass-a-Grille

Our pick of the best 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 NZ$572 per night from 6 July to 7 July
NZ$572
6 July - 7 July
includes taxes & fees
9.4/10 Exceptional! (3,399 reviews)
"A great escape! The beach was beautiful!! The Wyndham was very nice and clean! Staff was friendly and very helpful! Our balcony view was the perfect view of the gulf! Convenient spot, we walked or rode the trolley to restaurants and shops!"

Reviewed on 22 June 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 NZ$481 per night from 29 June to 30 June
NZ$481
29 June - 30 June
includes taxes & fees
Hilton Clearwater Beach Resort & Spa
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is NZ$426 per night from 28 June to 29 June
NZ$426
28 June - 29 June
includes taxes & fees
8.2/10 Very good! (2,053 reviews)
"This trip was supposed to be something special for my family. For starters there was a huge wasp nest on our balcony, which we were told would be taken care of - never was. Then our AC stopped working - they did offer to move us but by then it was day 3 of our trip. I was told that they were going ..."

Reviewed on 22 June 2026

RumFish Beach at TradeWinds
See all 16,894 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 holiday package cost?
Our Highpoint packages, which start at just , are the easiest way to save precious money. Select your favourite 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 holiday 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 Centre, an IHG Hotel or Intown Suites Extended Stay Clearwater Fl. Both offer comfortable beds and are popular options with many savvy travellers.
How far in advance should I book my Highpoint holiday?
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 holiday 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 holiday package is the most convenient way to organise 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 holiday 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 holiday package?
It's impossible to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Highpoint holiday 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

A coastal cityscape with a prominent waterfront, a bridge, and a distinctive building with a red facade.

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 seaside in this family-friendly area or visit its lively bars.

John's Pass Village & Boardwalk
Salvador Dali Museum

Salvador Dali Museum

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
Pier 60 Park

Pier 60 Park

Find appeal for all family members from dawn into late evening. Participate in the many exciting activities in this water wonderland.

Pier 60 Park

Activities

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

NZ$63
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The Pirate Ship at John's Pass

Pirate Adventure Cruise - John's Pass

NZ$77
per adult
94% of travellers recommend
Pirate Adventure Cruise - John's Pass
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

NZ$63
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
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.