Highpoint Vacations

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Highpoint Vacation

Take in everything this neighborhood has to offer with a tailor-made Highpoint vacation package. However you imagine yourself spending your days here, you'll find countless opportunities for adventure, relaxation and fun. Your trip to Highpoint wouldn't be complete without a visit to popular attractions nearby such as Tampa Bay Grand Prix, Feather Sound Country Club and Cove Cay Golf Club. No matter what your ideal Highpoint vacation looks like, you can turn it into reality with Expedia.

The Latest Highpoint Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 18
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.4/10 Very Good! (1,030 reviews)
Definitely going back 😍🏝️

Reviewed on May 22, 2024

The Avalon Club

The Avalon Club

4 out of 5
per person
Aug 15 - Aug 19
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.6/10 Exceptional! (297 reviews)
Loved everything about our stay at the Avalon Club! Beach access, easy access, parking, amazing staff, amazing room and views. Everything we were looking for and more!

Reviewed on May 21, 2024

Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
per person
Jul 30 - Aug 6
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.2/10 Very Good! (1,003 reviews)
Beautiful spot, staff was excellent, course was well maintained! No complaints at all. The rooms were clean, very welcoming! I will visit again!

Reviewed on May 19, 2024

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jun 29 - Jul 3
Roundtrip non-stop flight included
New York (NYC) to Tampa (TPA)
8.8/10 Excellent! (1,000 reviews)
It was awesome. Spotless room. Comfy beds. Fully stocked kitchenette. Delicious morning coffee in the lobby. Beautiful pool area. On the beach. Tiki bar was fun and super affordable. Lots of fun games to play. Putt Putt. Foosball. Ping pong. Giant chess and Jenga games. Cool places to hang out.

Reviewed on May 19, 2024

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

3.5 out of 5
Downtown Tampa
Save 100% on your flight
per person
Jun 24 - Jun 27
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
6.8/10 (1,357 reviews)
Hotel was very neat and clean. Victoria (?) at front desk was amazing!! Bartender in restaurant (Pilar?) very good. Pool bartender, not so much.

Reviewed on May 20, 2024

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

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 hotel + flight trips in Pass-a-Grille

Highpoint Hotel Deals

Sirata Beach Resort
Sirata Beach Resort
3 out of 5
5300 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is $164 per night from Jun 13 to Jun 14
$164
$230 total
includes taxes & fees
Jun 13 - Jun 14
7.2/10 Good! (2,244 reviews)
"Good place.nice fire pit open late on beach"

Reviewed on May 16, 2024

Sirata Beach Resort
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 $169 per night from Jun 2 to Jun 3
$169
$226 total
includes taxes & fees
Jun 2 - Jun 3
9/10 Wonderful! (1,870 reviews)
"Front desk guy that checked us in was not very friendly or helpful….some of your staff need more hospitality training…we had a great time in your beautiful resort"

Reviewed on May 20, 2024

Wyndham Grand Clearwater Beach
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 $135 per night from May 26 to May 27
$135
$153 total
includes taxes & fees
May 26 - May 27
8/10 Very Good! (1,009 reviews)
"Nice location"

Reviewed on May 19, 2024

The Westin Tampa Bay
See all 17,146 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Highpoint vacation package cost?
Our Highpoint packages, which start at just $345, 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

Image for John's Pass Village & Boardwalk

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 top-notch restaurants.

John's Pass Village & Boardwalk
Image for Tropicana Field

Tropicana Field

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the top-notch restaurants while you're in the area.

Tropicana Field
Image for 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

Image for StarLite Majesty Evening Yacht Cruise Clearwater

StarLite Majesty Evening Yacht Cruise Clearwater

$32
Per adult
86% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Image for Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

$60
Per adult
100% of travellers recommend
Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar
Image for 2-Hour Sunset Cruise Tour in St. Petersburg

2-Hour Sunset Cruise Tour in St. Petersburg

$67
Per adult
2-Hour Sunset Cruise Tour in St. Petersburg
See all activities in St. Petersburg - Clearwater

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.