Highpoint Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to ฿27,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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(3 area reviews)

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

Top hotels in Highpoint

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 ฿11,372 per night from 1 Jun to 2 Jun
฿11,372
฿14,124 total
1 Jun - 2 Jun
includes taxes & fees
9.4/10 Exceptional! (3,216 reviews)
Definitely returning. Amazing hospitality from the moment you drive up. Food choices could be better at the poolside bar, while food at ocean hai was very yummy, just expensive. all very worth it. Walking distance to pier 60 and many boat tours. Private beach chairs are such a nice perk with reasonable, ...

Reviewed on 7 May 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 ฿6,272 per night from 7 Jun to 8 Jun
฿6,272
฿8,362 total
7 Jun - 8 Jun
includes taxes & fees
8.2/10 Very Good! (2,605 reviews)
TIKI BAR ON THE BEACH WAS NICE TO ENJOY A NICE SUNSET. SERVICE WAS GOOD. BEACH VIEW WAS OK, SIDE VIEW OF THE GULF FROM OUR ROOM. ROOM WAS AVERAGE, NOTHING SPECIAL. GOT LOCKED OUT IN OUR BALCONY, HAD TO CALL THE FRONT DESK FOR MAINTENACE TO COME AND OPEN THE SLIDING DOOR. THE FRAME ON THE DOOR WAS ...

Reviewed on 6 May 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 ฿4,901 per night from 13 May to 14 May
฿4,901
฿7,541 total
13 May - 14 May
includes taxes & fees
7.6/10 Good! (1,136 reviews)
The pool was so crowded we could not get a seat. MANY children screaming. It was a bit too much! it was a great spot for the whole family. It was just my husband and I.

Reviewed on 5 May 2026

Island Grand at TradeWinds
See all 16,942 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.

Popular places to visit

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 visit its lively bars.

John's Pass Village & Boardwalk
Eckerd College

Eckerd College

Walk around the campus at Eckerd College as part of your travels around St. Petersburg. Amble around this family-friendly area's beautiful beaches and enjoy its top-notch restaurants.

Eckerd College
StPetersburg_JannusLive_553248621533125382_02

Jannus Live

Jannus Live is just one of the places to see in St. Petersburg, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Jannus Live

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

฿1,186
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

฿2,129
per adult
100% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

฿1,276
per adult
90% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
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.