Highpoint Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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
Price found within the past 48 hours. Click for updated prices.
Drury Plaza Hotel Tampa Brandon

Drury Plaza Hotel Tampa Brandon

3 out of 5
Price was €466, price is now €393 per person
€393
per person
10 Aug - 15 Aug
found 1 day ago
Return flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (9 reviews)
The kick back was nice but it was the same options every time. Pool and staff were great

Reviewed on 18 Jun 2026

Landing Tampa Westshore

Landing Tampa Westshore

4.5 out of 5
Port Tampa City
Price was €895, price is now €709 per person
€709
per person
10 Aug - 15 Aug
found 1 day ago
Return flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (194 reviews)
Todo, desde indication hasta tipo de muebles y servicios

Reviewed on 26 May 2026

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

4 out of 5
Beach Park
Price was €602, price is now €489 per person
€489
per person
10 Aug - 15 Aug
found 1 day ago
Return flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (1,817 reviews)
Everything was very clean and ran smoothly. Common areas were nice. However, beds have been an issue. We stayed here early 2025 and one of the double/queen beds had a dip in the mattress so large you could have literally sat a basketball in the hole. We turned the mattress so the hole was closer to the foot of the bed. On this recent trip we had a king bed, but was also so worn and old that there was a big dip in the middle of the mattress and it took effort to roll out of bed. Replace the mattresses! I don’t think we will return.

Reviewed on 17 Jun 2026

The Hemingway

The Hemingway

4 out of 5
Rocky Point
Price was €671, price is now €557 per person
€557
per person
10 Aug - 15 Aug
found 1 day ago
Return flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (27 reviews)
Was a nice stay. Enjoyed the pool and the view. Could’ve used more necessities such as cups, and towels.

Reviewed on 10 Apr 2026

Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
Price was €550, price is now €472 per person
€472
per person
10 Aug - 15 Aug
found 1 day ago
Return flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (2,634 reviews)
Great hotel with great staff. The place was cute and vibes were there!

Reviewed on 18 Jun 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
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

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 €159 per night from 19 Jul to 20 Jul
€159
19 Jul - 20 Jul
includes taxes & fees
8.6/10 Excellent! (1,372 reviews)
"Swimming pool was closed for our stay."

Reviewed on 15 Jun 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 €291 per night from 20 Jul to 21 Jul
€291
20 Jul - 21 Jul
includes taxes & fees
9.4/10 Exceptional! (3,379 reviews)
"Very welcoming place. Staff is pleasant and attentive. Located within walking distance to local attractions."

Reviewed on 18 Jun 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 €228 per night from 30 Jun to 1 Jul
€228
30 Jun - 1 Jul
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 19 Jun 2026

Hilton Clearwater Beach Resort & Spa
See all 16,858 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 €393, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.