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 2 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Tampa (TPA)
8.4/10 Very Good! (1,035 reviews)
Beautiful area. Rooms were nice just wished AC worked better in rooms. Staff is very friendly. Everything you need is within walking distance.

Reviewed on Jun 1, 2024

The Avalon Club

The Avalon Club

4 out of 5
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (297 reviews)
The property was really nice. It was across the street a park that the up-keeping was not that great.

Reviewed on May 27, 2024

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 19
found 1 day ago
Roundtrip flight included
Newark (EWR) to Tampa (TPA)
8.8/10 Excellent! (1,001 reviews)
We had a great time at the property!

Reviewed on Jun 1, 2024

TradeWinds Island Grand

TradeWinds Island Grand

4 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
7.6/10 Good! (1,014 reviews)
Beautiful location! The property is dated; however, the convenience and amenities make up for that. Front desk staff was not helpful when our flight was cancelled with advance notice and we needed to work with them and Expedia to refund one night’s stay. The check-in process was time-consuming and unwelcoming. We are dissatisfied that the hotel is not willing to work with us or Expedia to grant a refund for the night we were unable to stay there due to a cancelled flight because of severe weather in Texas.

Reviewed on Jun 1, 2024

Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

4 out of 5
Save 100% on your flight
per person
Aug 2 - Aug 6
found 1 day ago
Roundtrip flight included
Newark (EWR) to Tampa (TPA)
9/10 Wonderful! (1,650 reviews)
This was a great stay

Reviewed on May 31, 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

RumFish Beach Resort by TradeWinds
RumFish Beach Resort by TradeWinds
4 out of 5
6000 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is $161 per night from Jun 6 to Jun 7
$161
$244 total
includes taxes & fees
Jun 6 - Jun 7
8.2/10 Very Good! (1,011 reviews)
Great time!
"This hotel offered several fun things for the whole family to do. Plenty of pool Options, too! The on site restaurants are a little pricey (especially for my family of 7), but there is SO much within walking distance. We had a great time."

Reviewed on May 31, 2024

RumFish Beach Resort by TradeWinds
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 $155 per night from Jun 24 to Jun 25
$155
$221 total
includes taxes & fees
Jun 24 - Jun 25
7.2/10 Good! (2,249 reviews)
Great family resort!
"Great resort for families! We had a blast going from the beach to pool and to the splash pad. This resort had it all. Decent food and drink at their restaurants, and the daily live music was a nice touch too! We did encounter some minor hiccups, room keys kept deactivating, broken fan to name a couple, ..."

Reviewed on Jun 1, 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 $224 per night from Jun 2 to Jun 3
$224
$288 total
includes taxes & fees
Jun 2 - Jun 3
9/10 Wonderful! (1,871 reviews)
"Very nice but very expensive"

Reviewed on May 31, 2024

Wyndham Grand Clearwater Beach
See all 17,058 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 $556, 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

4.5/5(1,625 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 top-notch restaurants.

John's Pass Village & Boardwalk
Image for Tropicana Field

Tropicana Field

4.5/5(591 reviews)

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

4.5/5(676 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

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.